---
title: "Ashland Vacation Rentals, Oregon: house rentals & more | Vrbo"
description: "Explore an array of Ashland vacation rentals, including houses, cabins & more bookable online. Choose from more than 295 properties, ideal house rentals for families, groups and couples. Rent a whole home for your next weekend or vacation."
canonical: "https://www.vrbo.com/vacation-rentals/usa/oregon/southern-oregon/ashland"
language: en-US
market: US
currency: USD
prices_as_of: 2026-11-13T16:46:18Z
---

# Ashland vacation rentals
![A stone bridge over a calm stream with autumn leaves.](https://images.trvl-media.com/place/6290/8b9480db-b4f2-4804-8b28-cad8b8066a10.jpg?impolicy=resizecrop&rw=1920&ra=fit&ch=480)

We found 295 vacation rentals — enter your dates for availability

Immerse yourself in the enchanting charm of Ashland, where the majestic Cascade Mountains meet the serene waters of Emigrant Lake. This vibrant city invites you to explore its lush parks, like Lithia Park, and indulge in cultural treasures, such as the acclaimed Oregon Shakespeare Festival. With a variety of cozy cottages, spacious homes, and inviting apartments, Ashland’s vacation rentals offer the perfect blend of comfort and convenience for group travelers seeking unforgettable adventures together. Experience the freedom and warmth of a home away from home while creating lasting memories in this picturesque destination.

## Holiday rentals with weekly discounts - Ashland

### Showing deals for:**Feb 12 - Feb 19**

### [Tranquil setting surrounded by panoramic mountain views, grazing horses](https://www.vrbo.com/search?startDate=2027-02-12&endDate=2027-02-19&selected=27131289&adults=2)

![Kitchen](https://images.trvl-media.com/lodging/28000000/27140000/27131300/27131289/30486d75.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high)
- Location: Phoenix
- Guest rating: 10/10 (Exceptional, 135 reviews)
- Price: $139 (was $157, 11% off), $974 for 7 nights, All fees included

### [Gorgeous custom Airstream with spectacular views only 4 mi. to Ashland](https://www.vrbo.com/search?startDate=2027-02-12&endDate=2027-02-19&selected=33957942&adults=2)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33960000/33958000/33957942/eb852386.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high)
- Location: Talent
- Guest rating: 9.6/10 (Exceptional, 18 reviews)
- Price: $88 (was $96, 9% off), $615 for 7 nights, All fees included

### [Sunshine Studio - Private apt and yard (eco, solar)](https://www.vrbo.com/search?startDate=2027-02-12&endDate=2027-02-19&selected=78069033&adults=2)

![Room](https://images.trvl-media.com/lodging/79000000/78070000/78069100/78069033/4dab3273.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high)
- Location: Medford
- Guest rating: 9.8/10 (Exceptional, 115 reviews)
- Price: $104 (was $115, 9% off), $729 for 7 nights, All fees included

### [East Main Downtown Bungalow](https://www.vrbo.com/search?startDate=2027-02-12&endDate=2027-02-19&selected=68070529&adults=2)

![Living area](https://images.trvl-media.com/lodging/69000000/68080000/68070600/68070529/dc512f77.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high)
- Location: Ashland
- Guest rating: 9.2/10 (Wonderful, 56 reviews)
- Price: $142 (was $172, 17% off), $993 for 7 nights, All fees included

### [ABBOTT'S COTTAGES- Cardinal cottage. 1 bedroom/1 bath, short walk to downtown!](https://www.vrbo.com/search?startDate=2027-02-12&endDate=2027-02-19&selected=115924228&adults=2)

![Exterior detail](https://images.trvl-media.com/lodging/116000000/115930000/115924300/115924228/8b6a25ce.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high)
- Location: Ashland
- Guest rating: 9.6/10 (Exceptional, 5 reviews)
- Price: $129 (was $149, 13% off), $906 for 7 nights, All fees included

### [Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland](https://www.vrbo.com/search?startDate=2027-02-12&endDate=2027-02-19&selected=19825617&adults=2)

![Oberon](https://images.trvl-media.com/lodging/20000000/19830000/19825700/19825617/d50a77c7.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high)
- Location: Ashland
- Guest rating: 9.8/10 (Exceptional, 138 reviews)
- Price: $157 (was $171, 8% off), $1,099 for 7 nights, All fees included

### [Ashland's Mountain View Vacation Rental.](https://www.vrbo.com/search?startDate=2027-02-12&endDate=2027-02-19&selected=63932439&adults=2)

![Kitchen with new full size stainless steel appliances Coffee, teas or hot cocoa ](https://images.trvl-media.com/lodging/64000000/63940000/63932500/63932439/5a25c57f.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high)
- Location: Ashland
- Guest rating: 9.8/10 (Exceptional, 50 reviews)
- Price: $260 (was $285, 9% off), $1,818 for 7 nights, All fees included

### [Beautiful bungalow downtown Ashland railroad district, rv parking, adventure!](https://www.vrbo.com/search?startDate=2027-02-12&endDate=2027-02-19&selected=121825561&adults=2)

![Private kitchen](https://images.trvl-media.com/lodging/122000000/121830000/121825600/121825561/7b780ef9.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high)
- Location: Ashland
- Guest rating: 9/10 (Wonderful, 13 reviews)
- Price: $175 (was $210, 17% off), $1,227 for 7 nights, All fees included

### [ABBOTT'S COTTAGES- The Lark. 2 bedroom cottage, just two blocks to downtown](https://www.vrbo.com/search?startDate=2027-02-12&endDate=2027-02-19&selected=115971713&adults=2)

![Property grounds](https://images.trvl-media.com/lodging/116000000/115980000/115971800/115971713/de6ee1b7.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high)
- Location: Ashland
- Guest rating: 10/10 (Exceptional, 7 reviews)
- Price: $232 (was $255, 9% off), $1,626 for 7 nights, All fees included

### [ABBOTT'S COTTAGES, Avocet cottage- 3 bdrm/2bath, walking distance to downtown](https://www.vrbo.com/search?startDate=2027-02-12&endDate=2027-02-19&selected=113833953&adults=2)

![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113840000/113834000/113833953/21675980.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high)
- Location: Ashland
- Guest rating: 9.8/10 (Exceptional, 7 reviews)
- Price: $237 (was $273, 13% off), $1,659 for 7 nights, All fees included

### [ABBOTT'S COTTAGES - Falcon. 2 bedroom/2 bath within walking distance to downtown](https://www.vrbo.com/search?startDate=2027-02-12&endDate=2027-02-19&selected=115971137&adults=2)

![Exterior](https://images.trvl-media.com/lodging/116000000/115980000/115971200/115971137/98af5634.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high)
- Location: Ashland
- Guest rating: 9.4/10 (Exceptional, 10 reviews)
- Price: $252 (was $276, 9% off), $1,763 for 7 nights, All fees included

### [Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly](https://www.vrbo.com/search?startDate=2027-02-12&endDate=2027-02-19&selected=90085208&adults=2)

![Kitchen is well stocked ](https://images.trvl-media.com/lodging/91000000/90090000/90085300/90085208/795cc436.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high)
- Location: Ashland
- Guest rating: 9.8/10 (Exceptional, 87 reviews)
- Price: $270 (was $325, 17% off), $1,889 for 7 nights, All fees included

### [Titania - Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland](https://www.vrbo.com/search?startDate=2027-02-12&endDate=2027-02-19&selected=19838934&adults=2)

![Exterior](https://images.trvl-media.com/lodging/20000000/19840000/19839000/19838934/87817502.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high)
- Location: Ashland
- Guest rating: 10/10 (Exceptional, 87 reviews)
- Price: $196 (was $213, 8% off), $1,369 for 7 nights, All fees included

### [Premier Downstairs Flat in Perfect Down Town Location](https://www.vrbo.com/search?startDate=2027-02-12&endDate=2027-02-19&selected=57755559&adults=2)

![Exterior](https://images.trvl-media.com/lodging/58000000/57760000/57755600/57755559/871bb930.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high)
- Location: Ashland
- Guest rating: 10/10 (Exceptional, 93 reviews)
- Price: $252 (was $305, 18% off), $1,762 for 7 nights, All fees included

### [New Downtown 3 Bedroom Upstairs Flat with views](https://www.vrbo.com/search?startDate=2027-02-12&endDate=2027-02-19&selected=70975536&adults=2)

![Primary bedroom](https://images.trvl-media.com/lodging/71000000/70980000/70975600/70975536/4904e5f8.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high)
- Location: Ashland
- Guest rating: 9.8/10 (Exceptional, 52 reviews)
- Price: $258 (was $313, 18% off), $1,807 for 7 nights, All fees included

## Find spaces that suit your style

[Search for Houses](https://www.vrbo.com/search?destination=Ashland%2C+Oregon%2C+United+States+of+America&regionId=6290&latLong=42.19672%2C-122.713948&adults=2&startDate=2026-11-27&d1=2026-11-27&endDate=2026-11-29&d2=2026-11-29&property%5Ftype%5Fgroup=house)

House

[Search for Condos/Apartments](https://www.vrbo.com/search?destination=Ashland%2C+Oregon%2C+United+States+of+America&regionId=6290&latLong=42.19672%2C-122.713948&adults=2&startDate=2026-11-27&d1=2026-11-27&endDate=2026-11-29&d2=2026-11-29&property%5Ftype%5Fgroup=apartment%5For%5Fcondo)

Condo/Apartment

[search for cabins](https://www.vrbo.com/search?destination=Ashland%2C+Oregon%2C+United+States+of+America&regionId=6290&latLong=42.19672%2C-122.713948&adults=2&startDate=2026-11-27&d1=2026-11-27&endDate=2026-11-29&d2=2026-11-29&property%5Ftype%5Fgroup=cabin)

Cabin

[search for cottages](https://www.vrbo.com/search?destination=Ashland%2C+Oregon%2C+United+States+of+America&regionId=6290&latLong=42.19672%2C-122.713948&adults=2&startDate=2026-11-27&d1=2026-11-27&endDate=2026-11-29&d2=2026-11-29&property%5Ftype%5Fgroup=cottage)

Cottage

[search for villas](https://www.vrbo.com/search?destination=Ashland%2C+Oregon%2C+United+States+of+America&regionId=6290&latLong=42.19672%2C-122.713948&adults=2&startDate=2026-11-27&d1=2026-11-27&endDate=2026-11-29&d2=2026-11-29&property%5Ftype%5Fgroup=villa)

Villa

[search for chalets](https://www.vrbo.com/search?destination=Ashland%2C+Oregon%2C+United+States+of+America&regionId=6290&latLong=42.19672%2C-122.713948&adults=2&startDate=2026-11-27&d1=2026-11-27&endDate=2026-11-29&d2=2026-11-29&property%5Ftype%5Fgroup=chalet)

Chalet

## Find properties near top attractions in Ashland

![A statue of a person in a brown outfit with a hat and sunglasses, holding a pipe and a book, standing on a pedestal in a park with green bushes and trees.](https://images.trvl-media.com/place/6290/b7ae12c5-31b7-437b-8947-0bfe6b9d08cf.jpg?impolicy=fcrop&w=600&h=400&p=1&q=medium)

1

###### [Oregon Shakespeare Festival](https://www.vrbo.com/search?regionId=6183594&startDate=&endDate=&locale=en%5FUS&rfrrid=slp)

![A wood duck standing on rocks with moss and greenery in the background.](https://images.trvl-media.com/place/553248621532642212/4ef58f19-de19-4351-bf68-0d92a6cbf1ec.jpg?impolicy=fcrop&w=600&h=400&p=1&q=medium)

2

###### [Lithia Park](https://www.vrbo.com/search?regionId=553248621532642212&startDate=&endDate=&locale=en%5FUS&rfrrid=slp)

![A snowy forest with tall evergreen trees covered in snow.](https://images.trvl-media.com/place/6087455/da84e456-ba2e-4cc1-a63a-455c73ca7334.jpg?impolicy=fcrop&w=600&h=400&p=1&q=medium)

3

###### [Mount Ashland Ski Area](https://www.vrbo.com/search?regionId=6087455&startDate=&endDate=&locale=en%5FUS&rfrrid=slp)

## Find the best place to stay - Ashland

### [Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly](https://www.vrbo.com/3167318?containsVideo=false)

![Image of Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly](https://media.vrbo.com/lodging/91000000/90090000/90085300/90085208/795cc436.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455)
- Address: Ashland, OR
- Guest rating: 9.8/10 (Exceptional, 87 reviews)

Premier Host

Sleeps 8 · 3 bedrooms · 2 bathrooms

### [Premier Downstairs Flat in Perfect Down Town Location](https://www.vrbo.com/2056462?containsVideo=false)

![Image of Premier Downstairs Flat in Perfect Down Town Location ](https://media.vrbo.com/lodging/58000000/57760000/57755600/57755559/871bb930.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455)
- Address: Ashland, OR
- Guest rating: 10/10 (Exceptional, 93 reviews)

Premier Host

Sleeps 6 · 3 bedrooms · 2 bathrooms

### [The Ashland Cottage, walk to town](https://www.vrbo.com/651189?containsVideo=false)

![Image of The Ashland Cottage, walk to town](https://media.vrbo.com/lodging/19000000/18980000/18973800/18973754/fc87b003.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455)
- Address: Ashland, OR
- Guest rating: 10/10 (Exceptional, 241 reviews)

Premier Host

Sleeps 4 · 1 bedroom · 1+ bathroom

### [Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland](https://www.vrbo.com/560782?containsVideo=false)

![Image of Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland ](https://media.vrbo.com/lodging/20000000/19830000/19825700/19825617/d50a77c7.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455)
- Address: Ashland, OR
- Guest rating: 9.8/10 (Exceptional, 138 reviews)

Premier Host

Sleeps 3 · 1 bedroom · 1 bathroom

### [Hyatt Lake Mountain Retreat](https://www.vrbo.com/2004745?containsVideo=false)

![Image of Hyatt Lake Mountain Retreat](https://media.vrbo.com/lodging/56000000/55020000/55010300/55010257/25eb62a7.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455)
- Address: Ashland, OR
- Guest rating: 9.8/10 (Exceptional, 104 reviews)

Premier Host

Sleeps 7 · 3 bedrooms · 1 bathroom

### [A Cowslip's Belle Inn](https://www.vrbo.com/pdp/lo/95265593?containsVideo=false)

![Image of A Cowslip's Belle Inn](https://media.vrbo.com/lodging/96000000/95270000/95265600/95265593/f33edd7e.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455)
- Address: 159 N Main St, Ashland, OR, 97520
- Guest rating: 9.6/10 (Exceptional, 56 reviews)

## Top rated rentals - Ashland

### [Paschal Winery](https://www.vrbo.com/pdp/lo/104007590?containsVideo=false)

![Image of Paschal Winery](https://media.vrbo.com/lodging/105000000/104010000/104007600/104007590/49be0da4.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455)

- Guest rating: 9.8/10 (Exceptional, 19 reviews)
- Review: Excellent Winery Lodging. A wonderful winery to stay at between Ashland and Medford. The Paschal Winery had lovely accommodations, and we stayed three nights in a glamping trailer. The winery has excellent wines, amazing food, and we had three great bands to listen to during the weekend. We'd stay there again for sure. The vineyards are a beautiful setting to relax in, watch sunsets and star gaze., by Denise, Stayed Sep 2025

### Peace of mind
Our Book with Confidence guarantee gives you 24/7 support

### All the privacy of home
Enjoy full kitchens, laundry, pools, yards and more

### More for less
More space, more privacy, more amenities — more value

### A place for everyone
We stand for diversity, inclusion and families everywhere.
[Learn more](https://www.vrbo.com/vacation-ideas/explore-vrbo/inclusion-and-diversity)

## Find out more about Ashland

### Why visit Ashland

- **Outdoor Adventures:**  Ashland is perfect for nature lovers, offering stunning lakes and urban parks for hiking, biking, and exploring.
- **Cultural Richness:**  The city boasts a vibrant arts scene, highlighted by local theaters, galleries, and cultural events.
- **Wine Country:**  Visit local vineyards to enjoy some of the finest wines the region has to offer.
- **Charming Accommodations:**  Choose from cozy cottages to modern apartments that provide a comfortable stay for every traveler.
- **Friendly Atmosphere:**  Ashland's welcoming vibe makes it ideal for romantic getaways, family vacations, and summer retreats.

### Popular types of accommodation in Ashland

Planning a getaway to Ashland? Exciting times await as you select your perfect accommodation. Discover a variety of options, from charming houses and cozy cottages to modern apartments. Whether you're searching for spacious house rentals or intimate vacation homes, Ashland offers an array of Oregon vacation rentals that cater to every traveler's needs. Get ready to relax and enjoy your stay in this beautiful town.

- **[Houses: ](https://www.vrbo.com/vacation-rentals/houses/usa/oregon/southern-oregon/ashland)** These spacious homes are the top choice for visitors in Ashland, offering a homey atmosphere perfect for families or groups.
- **[Cottages: ](https://www.vrbo.com/vacation-rentals/cottages/usa/oregon/southern-oregon/ashland)** Quaint and cozy, cottages are a charming option for those seeking a peaceful getaway in Ashland.
- **[Apartments: ](https://www.vrbo.com/vacation-rentals/condos-and-apartments/usa/oregon/southern-oregon/ashland)** Ideal for solo travelers or couples, apartments provide convenient and comfortable accommodations in the heart of the city.
- **[Cabins: ](https://www.vrbo.com/vacation-rentals/cabins/usa/oregon/southern-oregon/ashland)** Rustic cabins offer a unique experience, blending nature with comfort for a relaxing retreat.
- **Chalets:**  These alpine-style lodgings provide a picturesque setting for a memorable stay in Ashland.\*\*

### Top attractions in Ashland

Ashland, Oregon, is perfect for outdoor enthusiasts and adventure seekers, offering stunning scenery and a rich cultural experience. Explore beautiful lakes, visit modern colleges and universities, and enjoy urban parks that cater to a variety of interests. Whether you're traveling solo, with family, or friends, Ashland promises an unforgettable getaway filled with exciting attractions and natural beauty.

- **[Southern Oregon University: ](https://www.vrbo.com/vacation-rentals/usa/oregon/ashland/southern-oregon-university)** A modern campus bustling with city vibes, Southern Oregon University offers a vibrant atmosphere with beautiful architecture and a variety of cultural events. You'll find students engaged in a range of activities, making it a lively spot to explore.
- **[Lithia Park: ](https://www.vrbo.com/vacation-rentals/usa/oregon/ashland/lithia-park)** This urban park is a family-friendly gem in Ashland, featuring lush greenery, walking trails, and serene ponds. Perfect for a leisurely stroll or a picnic, the park provides a peaceful escape while still feeling connected to the city.
- **[Howard Prairie Lake: ](https://www.vrbo.com/vacation-rentals/usa/oregon/southern-oregon/howard-prairie-lake)** A picturesque lake surrounded by stunning scenery, Howard Prairie Lake is ideal for outdoor lovers. Enjoy beach activities, fishing, or a romantic sunset by the water's edge, making it a perfect getaway for nature enthusiasts.

### Things to do recommended for couples

Planning a romantic getaway in Ashland? Enjoy skiing together at [Mount Ashland Ski Area](https://www.vrbo.com/vacation-rentals/usa/oregon/ashland/mount-ashland-ski-area), savor exquisite wines at [Paschal Winery](https://www.vrbo.com/vacation-rentals/usa/oregon/ashland/paschal-winery) just 5 miles away, or take an adventurous ride on the [Ariel Ski Lift](https://www.vrbo.com/vacation-rentals/usa/oregon/medford/ariel-ski-lift). Each experience promises to create unforgettable memories for you both.

### Things to do recommended for families

Families can unwind at [Howard Prairie County Resort](https://www.vrbo.com/tgp/vacation-rental/871877635937050624/howard-prairie-county-resort), enjoying its serene atmosphere. For a fun adventure, head to [Rogue Valley Family Fun Center](https://www.vrbo.com/vacation-rentals/usa/oregon/central-point/rogue-valley-family-fun-center), just 16 miles away, where excitement awaits. Additionally, Howard Prairie County Recreation Area offers more relaxation and outdoor activities for everyone.

### Things to do recommended for groups

Experience the magic of the [Oregon Shakespeare Festival](https://www.vrbo.com/vacation-rentals/usa/oregon/ashland/oregon-shakespeare-festival) for an evening of culture and entertainment. For adventure lovers, hike the [Bull Gap Lower Trailhead](https://www.vrbo.com/vacation-rentals/united-states-of-america/oregon/jackson-county/ashland/bull-gap-lower-trailhead) and enjoy stunning scenery. Don't miss the [Lithia Artisans Market](https://www.vrbo.com/vacation-rentals/usa/oregon/ashland/lithia-artisans-market) for a taste of local business and city vibes.

*\*Distances are measured in a straight line; actual driving distances may vary depending on the route.*

### What do I need to keep in mind when booking a vacation in Ashland

If you're traveling with a group, family, pets, or planning an extended stay, it's important to set your priorities when filtering options. Here are some helpful Vrbo booking tips to assist you.

- **[Traveling to Ashland with a group: ](https://www.vrbo.com/search?bedroom%5Fcount%5Fgt=3&regionId=6290&rooms%5Fspaces%5Fgroup=kitchen&rfrr=crcontent)** Think about how many bedrooms you require, as well as features like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
- **[Traveling to Ashland with young kids: ](https://www.vrbo.com/search?house%5Frules%5Fgroup=children%5Fallowed&properties%5Fgood%5Ffor%5Fgroup=families&regionId=6290&rfrr=crcontent)** Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with amenities that suit their age, like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
- **[Taking your pets with you to Ashland: ](https://www.vrbo.com/search?house%5Frules%5Fgroup=pets%5Fallowed&regionId=6290&amenities=PETS&rfrr=crcontent)** For many families, a vacation isn't truly fulfilling without their furry companion by their side. If you can relate, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that all family members, including your four-legged friends, feel comfortable and at home.
- **Planning for a long term stay visiting Ashland:**  If you're in search of vacation rentals with discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don’t forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

### Where to stay in and around Ashland

Exploring Ashland, Oregon, offers a delightful blend of outdoor adventures and stunning scenery. Known for its friendly atmosphere, this charming city is perfect for romantic getaways, family vacations, or summer retreats. Be sure to visit local vineyards for a taste of the region's finest wines, and immerse yourself in the vibrant arts scene. Ashland's nearby attractions promise unforgettable experiences, making it a must-visit destination for every traveler.

- **[Historic Downtown District: ](https://www.vrbo.com/vacation-rentals/usa/oregon/southern-oregon/ashland/historic-downtown-di)** The Historic Downtown District of Ashland is a charming neighborhood that captivates visitors with its romantic ambiance and family-friendly attractions. Nestled in the heart of Ashland, this area is known for its vibrant arts scene and a plethora of outdoor activities. Explore the renowned Oregon Shakespeare Festival, indulge in unique shops and galleries, and enjoy delicious dining options. With stunning parks and scenic hiking trails nearby, as well as access to the beautiful local lake and national parks, this district offers a perfect blend of culture and nature for all types of travelers.
- **[Talent: ](https://www.vrbo.com/vacation-rentals/usa/oregon/southern-oregon/talent)** Located just 5 miles from Ashland, Talent is a delightful city that beckons adventure seekers and nature lovers alike. Known for its stunning scenery and recreational opportunities, Talent offers a range of outdoor activities, including hiking, fishing, and skiing in the winter months. Visitors can explore the local parks and enjoy the community's vibrant arts and theater scene. With its proximity to beautiful lakes and national parks, Talent is an ideal destination for those looking to immerse themselves in the great outdoors while enjoying the charm of a small town.
- **[Historic Railroad District: ](https://www.vrbo.com/vacation-rentals/usa/oregon/southern-oregon/ashland/historic-railroad-di)** The Historic Railroad District is another gem in Ashland, offering a delightful mix of outdoor adventures and family-friendly fun. This picturesque neighborhood is rich in history and features a variety of attractions, including theaters and hiking trails. Visitors can easily access ski resorts in the winter, making it a year-round destination for outdoor enthusiasts. With its beautiful lake and the nearby national state park, the Historic Railroad District provides a perfect setting for romantic getaways and family excursions alike, all within walking distance of Ashland's vibrant downtown.

### Best time to go to Ashland

If you're planning a trip to Ashland, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and June to July, while off-peak times, like October to December tend to have fewer bookings and better deals.

| **Calendar Month** | **Temperature** | **Precipitation** | **Cloudiness** | **Occupancy** | **Pricing**   |
| ------------------ | --------------- | ----------------- | -------------- | ------------- | ------------- |
| January            | 36.3°F (2.4°C)  | Light Rain        | Mostly Sunny   | Average       | Slightly Low  |
| February           | 37.2°F (2.9°C)  | Light Rain        | Mostly Sunny   | Average       | Slightly Low  |
| March              | 40.5°F (4.7°C)  | Light Rain        | Mostly Sunny   | Average       | Average       |
| April              | 46.0°F (7.8°C)  | Light Rain        | Mostly Sunny   | Slightly High | Slightly Low  |
| May                | 53.2°F (11.8°C) | Light Rain        | Mostly Sunny   | Average       | Average       |
| June               | 60.4°F (15.8°C) | No Rain (Dry)     | Mostly Sunny   | Slightly High | Slightly High |
| July               | 69.3°F (20.7°C) | No Rain (Dry)     | Sunny          | Slightly High | Slightly High |
| August             | 68.7°F (20.4°C) | No Rain (Dry)     | Sunny          | Average       | Slightly High |
| September          | 61.5°F (16.4°C) | No Rain (Dry)     | Sunny          | Average       | Average       |
| October            | 51.1°F (10.6°C) | Light Rain        | Mostly Sunny   | Slightly Low  | Average       |
| November           | 40.8°F (4.9°C)  | Light Rain        | Mostly Sunny   | Slightly Low  | Average       |
| December           | 34.7°F (1.5°C)  | Light Rain        | Mostly Sunny   | Slightly Low  | Average       |

### Booking with Vrbo is simple

Are you hoping to cut costs on your next adventure? Being flexible with your travel dates can help, as prices often vary. Additionally, booking an extended stay can lead to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to narrow down options by price, location, and type of vacation rental.

### Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform where you can easily create new trips, resume your planning, or manage your existing itineraries. You’ll be able to see your saved or booked properties organized into sections for Potential, Upcoming, or Current Trips. To begin using Trip Boards, head over to: https://www.vrbo.com/trips.

\*\*Based on Vrbo properties bookings.

## Frequently Asked Questions

### What is the best area to stay in Ashland, Oregon, United States of America when booking a vacation rental?

When looking for the best area to stay in Ashland, Oregon, the Historic District is a fantastic choice. This charming neighborhood is known for its picturesque streets and proximity to the Oregon Shakespeare Festival, a major attraction that draws visitors from all over to enjoy world-class performances. Additionally, the nearby Lithia Park offers beautiful trails, gardens, and a serene environment superb for relaxation and outdoor activities.

Another appealing area is the Ashland Creek neighborhood, which provides a more laid-back atmosphere while still being close to downtown. Here, you can explore local shops, art galleries, and cafes, making it a great spot for those who appreciate a vibrant arts scene. The proximity to both the festival and the stunning natural beauty of the surrounding mountains enhances the appeal of this area.

In terms of vacation rentals, both neighborhoods offer a variety of options, from cozy cottages to more spacious homes, allowing you to find the superb fit for your stay.

### How much does it cost to rent a vacation home in Ashland?

Prices for vacation rentals in Ashland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from [affordable rentals in Ashland](https://www.vrbo.com/search?regionId=6290&sort=PRICE%5FLOW%5FTO%5FHIGH) to more spacious homes. To get the best value, book early and take advantage of [Vrbo’s free rewards program](https://www.vrbo.com/welcome-one-key).

### Are there any discounts for Ashland vacation house rentals?

You can find great discounts on house rentals in Ashland on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.

### Where are the best Ashland ski resort rentals?

For skiing near Ashland, the best options are centered around the Mount Ashland Ski Area, which is just a short drive from the town. In Ashland, travelers can find a range of vacation rentals, from cozy cabins to larger homes that cater to families or groups. Many properties feature amenities like wood-burning stoves or fireplaces, making them great for après-ski relaxation. Fully equipped kitchens are common, allowing guests to prepare meals after a day on the slopes.

In the downtown area of Ashland, visitors can enjoy a vibrant arts scene, with easy access to local shops, restaurants, and the famous Oregon Shakespeare Festival. Some rentals in this area offer outdoor spaces like decks or patios, where guests can unwind while taking in the beautiful mountain views.

Additionally, the surrounding Ashland National Forest provides opportunities for outdoor activities beyond skiing, such as snowshoeing and hiking. Many rentals are conveniently located near these natural attractions, enhancing the overall experience for guests who wish to explore the stunning landscapes of Southern Oregon.

### What is the most popular type of vacation rental accomodation in Ashland?

In Ashland, [vacation houses](https://www.vrbo.com/vacation-rentals/houses/usa/oregon/southern-oregon/ashland) are the most popular type of rental, with about 88 available throughout the area. These homes are often located in serene neighborhoods, providing a spacious and comfortable environment ideal for families or larger groups. Most vacation houses come equipped with multiple bedrooms, fully furnished kitchens, and outdoor spaces for relaxation or dining al fresco, allowing guests to enjoy the beautiful surroundings. Additionally, there are around 50 apartments available, which cater to those seeking a more compact living option, often featuring modern amenities and convenient access to local attractions like the Oregon Shakespeare Festival and Lithia Park. For a more quaint stay, approximately 40 cottages and several cabins offer unique charm and rustic appeal, typically set against picturesque backdrops.

### Are there any family house rentals in Ashland?

In Ashland, Oregon, there are numerous family-friendly vacation rentals available, with around 87 options to choose from. The downtown area is particularly appealing, as it offers easy access to the renowned Oregon Shakespeare Festival and a variety of parks, great for family outings. Many homes in this locale feature spacious living areas, fully equipped kitchens for family meals, and outdoor spaces for kids to enjoy.

Travelers can also find properties with amenities such as game rooms, hot tubs, and cozy fireplaces, providing comfort and entertainment for all ages. Nearby attractions, including Lithia Park with its playgrounds and walking trails, add to the area's family-friendly charm.

### Can I rent a vacation home with a pool or hot tub in Ashland?

In Ashland, there are some vacation homes available for rent that feature pools and hot tubs, with around 11 options to choose from. This charming town, known for its vibrant arts scene and proximity to the stunning Rogue Valley, offers a range of neighborhoods where these properties can be found. Many rentals come equipped with private pools, hot tubs, and spacious outdoor areas, ideal for relaxation after a day of exploring.

Travelers can expect amenities such as fully equipped kitchens, comfortable living spaces, and sometimes even outdoor dining areas that enhance the experience of enjoying the beautiful Oregon weather. Additionally, some properties may offer scenic views of the surrounding landscape, making them great for unwinding in a tranquil setting.

### Can I find long-stay vacation rentals in Ashland?

A long-stay vacation rental in Ashland is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.\* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

 \*Based on analysis of Vrbo booking and occupancy data for 2024 stays.

### Are there pet-friendly house rentals in Ashland?

In Ashland, travelers will find a variety of pet-friendly house rentals, with over 100 options available to choose from. Many of these rentals are situated in charming neighborhoods that offer a blend of scenic beauty and convenient access to local attractions. Visitors can expect amenities such as spacious backyards for pets to roam, fully equipped kitchens for self-catering, and comfortable living spaces ideal for relaxing after a day of exploration.

The area is known for its vibrant arts scene, and staying in Ashland provides easy access to the famous Oregon Shakespeare Festival, as well as local parks and nature trails that welcome pets. Lithia Park, located in the heart of downtown, features expansive green spaces, walking paths, and even a dog park, making it a great spot for pet owners to enjoy outdoor activities.

### Are there any remote work vacation rentals in Ashland?

In Ashland, Oregon, there are numerous options for remote work vacation rentals, with around 162 available. This vibrant town, known for its arts scene and proximity to the stunning Cascade Mountains, provides a variety of accommodations that cater to remote workers. Many properties feature dedicated office spaces with desks and ergonomic chairs, high-speed internet, and even computer monitors, ensuring a productive work environment.

Travelers can expect properties equipped with modern amenities, including fully stocked kitchens for meal preparation, cozy living areas for relaxation, and sometimes outdoor spaces for those much-needed breaks. Ashland's charming downtown area, with its shops, cafes, and the renowned Oregon Shakespeare Festival, adds an element of cultural enrichment to the work-from-home experience. To help narrow your search, insert your dates and apply the "[WiFi](https://www.vrbo.com/search?regionId=6290&amenities%5Ffacilities%5Fgroup=internet%5Favailable)" filter on Vrbo.

### Are there any Ashland vacation rentals with parking?

Vrbo offers a wide selection of [vacation rentals in Ashland with parking](https://www.vrbo.com/search?regionId=6290&amenities%5Ffacilities%5Fgroup=parking) available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the “Parking available” filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.

### What are popular rental amenities in Ashland?

In Ashland, popular vacation rental amenities include fully equipped kitchens, allowing travelers to prepare their own meals and enjoy home-cooked dining experiences. Many rentals also offer onsite parking, which is convenient for those traveling with vehicles. Outdoor spaces such as decks or patios are common, providing a ideal setting for relaxation after a day of exploring the charming downtown or attending a performance at the Oregon Shakespeare Festival. Additionally, coffee and tea makers are typically available, suiting those who enjoy a warm beverage in the morning. For pet owners, several properties permit pets, making it easier for guests to bring their furry companions along on their adventures.

### When is the best time to visit Ashland for a vacation rental?

The best time to visit Ashland for a vacation rental is during the peak season from June to August, particularly in July when the town comes alive with vibrant activities and events. This period is great for travelers who appreciate outdoor adventures, as the warm temperatures (ranging from the low 50s to high 80s Fahrenheit) create ideal conditions for hiking, exploring local parks, and attending the celebrated Oregon Shakespeare Festival.

During these summer months, visitors can take part in the lively option of Ashland, enjoying not only the scenic beauty of the area but also the rich cultural experiences it offers. The lush landscapes and nearby trails provide ample opportunities for sightseeing and outdoor recreation, ensuring that every adventure seeker finds something to delight in.

If you're looking for a more budget-friendly option, consider visiting in December. This month offers a unique charm, with fewer tourists and the opportunity to enjoy a quieter experience while still appreciating the festive holiday spirit. Ashland's cozy ambiance during this time can be particularly appealing for those who prefer a relaxed getaway.

Ultimately, your ideal time to visit Ashland will depend on whether you seek the bustling energy of summer or the tranquil beauty of winter.

### How early should I book a Ashland vacation rental?

Book your Ashland vacation rental at least two months before you travel for the best selection of properties.\* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

 \*Based on analysis of Vrbo booking and occupancy data for 2024 stays.

### What are the top attractions in Ashland, Oregon, United States of America?

In Ashland, visitors can explore a variety of attractions that showcase the town's unique culture and natural beauty. The Oregon Shakespeare Festival, located in the heart of downtown, is a major draw, offering a diverse range of performances throughout the year. Nearby, Lithia Park provides a scenic outdoor space with walking trails, gardens, and a picturesque pond, making it ideal for leisurely strolls or picnics.

The historic district features charming shops, art galleries, and cafes, allowing travelers to experience local artisan crafts and cuisine. For those interested in the arts, the Ashland Art Center is a great spot to see local artwork and participate in workshops.

Nature enthusiasts can venture to the surrounding areas, such as the breathtaking Mount Ashland, which offers hiking trails and stunning views, particularly during the fall when the foliage is vibrant.

### Can I change or cancel my Ashland home rental booking on Vrbo?

To find Ashland vacation rentals with free cancellation, just use Vrbo's handy "[Free cancellation](https://www.vrbo.com/search?regionId=6290&free%5Fcancellation%5Fgroup=free%5Fcancellation)" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with [Affirm](https://www.vrbo.com/search?regionId=6290&booking%5Foptions%5Fgroup=pay%5Flater%5Fwith%5Faffirm). Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.

### Why should I join Vrbo as a host?

Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, [become a host](https://www.vrbo.com/en-us/list) and let Vrbo handle the heavy lifting to help you thrive.

 Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

### Are all fees included in the Ashland vacation rental prices shown on Vrbo?

Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

### What is VrboCare™ and how does it work?

Vrbo’s mission is to help guests relax, reconnect, and enjoy precious time together. With [VrboCare™](https://www.vrbo.com/tlp/trust-and-safety/care-guarantee), you can have peace of mind knowing you’re protected and that if something goes wrong, we will do our best to make it right as applicable.

 If a significant issue arises that your host can’t resolve, we’ll help you address it, find a similar property, or get your reservation refunded if applicable. That’s our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.

### What can I expect from Vrbo customer service and VrboCare™ support?

Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

 Vrbo also offers support via live chat through our [Help Center](https://www.vrbo.com/helpcenter/?articleId=40104), where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.

### Can I plan a group trip on Vrbo?

Vrbo's [Trip Planner](https://www.vrbo.com/why/trip-planning) makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

## More vacation ideas

- [Lodging](?equalTargetTab=tab-0)
- [Vacation Rentals](?equalTargetTab=tab-1)
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- [Siskiyou-Hargadine Historic District Vacation Rentals](https://www.vrbo.com/vacation-rentals/usa/oregon/southern-oregon/ashland/siskiyou-hargadine-d)
- [City Center Medford Vacation Rentals](https://www.vrbo.com/vacation-rentals/usa/oregon/medford/city-center-medford)
- [Gold Hill Vacation Rentals](https://www.vrbo.com/vacation-rentals/usa/oregon/southern-oregon/gold-hill)
- [White City Vacation Rentals](https://www.vrbo.com/vacation-rentals/usa/oregon/white-city)
- [Applegate Vacation Rentals](https://www.vrbo.com/vacation-rentals/usa/oregon/southern-oregon/applegate)
- [Rogue River Vacation Rentals](https://www.vrbo.com/vacation-rentals/usa/oregon/southern-oregon/rogue-river)
- [Ruch Vacation Rentals](https://www.vrbo.com/vacation-rentals/usa/oregon/southern-oregon/ruch)
- [Shady Cove Vacation Rentals](https://www.vrbo.com/vacation-rentals/usa/oregon/southern-oregon/shady-cove)
- [Williams Vacation Rentals](https://www.vrbo.com/vacation-rentals/usa/oregon/southern-oregon/williams)
- [Trail Vacation Rentals](https://www.vrbo.com/vacation-rentals/usa/oregon/trail)
- [Grants Pass Vacation Rentals](https://www.vrbo.com/vacation-rentals/usa/oregon/southern-oregon/grants-pass)
- [Rocky Point Vacation Rentals](https://www.vrbo.com/vacation-rentals/usa/oregon/southern-oregon/rocky-point)
- [Prospect Vacation Rentals](https://www.vrbo.com/vacation-rentals/usa/oregon/southern-oregon/prospect)
- [Merlin Vacation Rentals](https://www.vrbo.com/vacation-rentals/usa/oregon/southern-oregon/merlin)
- [Southern Oregon Vacation Rentals](https://www.vrbo.com/vacation-rentals/usa/oregon/southern-oregon)
- [Klamath Falls Vacation Rentals](https://www.vrbo.com/vacation-rentals/usa/oregon/southern-oregon/klamath-falls)
- [Cave Junction Vacation Rentals](https://www.vrbo.com/vacation-rentals/usa/oregon/southern-oregon/cave-junction)
- [Downtown Klamath Falls Vacation Rentals](https://www.vrbo.com/vacation-rentals/usa/oregon/downtown-klamath-falls)

## Other language versions

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hreflang:
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  en-CA: https://www.vrbo.com/en-ca/vacation-rentals/united-states/oregon/jackson-county/ashland
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  ja-JP: https://www.vrbo.com/ja-jp/%E5%AE%BF%E6%B3%8A/%E3%82%A2%E3%83%A1%E3%83%AA%E3%82%AB/%E3%82%AA%E3%83%AC%E3%82%B4%E3%83%B3%E5%B7%9E/jackson-county/%E3%82%A2%E3%83%83%E3%82%B7%E3%83%A5%E3%83%A9%E3%83%B3%E3%83%89
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  sv-SE: https://www.vrbo.com/sv-se/semesterbostad/usa/oregon/jackson-county/ashland
  fr: https://www.abritel.fr/d/715/ashland
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```