Ashland vacation rentals

We found 289 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:Dec 11 - Dec 18

Front of house
Pool
Fire pit. 
Perfect for chilly nights.
Dining room
Exceptional
(38 reviews)

Come stay at our farmhouse! A place to integrate all the beauty surrounding you!

Ashland

9% off
$851
$5,958 for 7 nights
All fees included
Come stay at our farmhouse! A place to integrate all the beauty surrounding you!
Kitchen
Kitchen
Double Rainbow
Exterior
Exceptional
(131 reviews)

Tranquil setting surrounded by panoramic mountain views, grazing horses

Phoenix

11% off
$144
$1,008 for 7 nights
All fees included
Tranquil setting surrounded by panoramic mountain views, grazing horses
Room
Private kitchen
Outdoor dining
Interior
Wonderful
(9 reviews)

Beautiful bungalow downtown Ashland railroad district, rv parking, adventure!

Ashland

16% off
$184
$1,290 for 7 nights
All fees included
Beautiful bungalow downtown Ashland railroad district, rv parking, adventure!
Private kitchen
Exterior
Living area
Exterior detail
Exceptional
(82 reviews)

Premier Downstairs Flat in Perfect Down Town Location

Ashland

17% off
$254
$1,781 for 7 nights
All fees included
Premier Downstairs Flat in Perfect Down Town Location
Room
Dining
Living area
Your friendly host(s) are often in the small cabin in case you need anything. :)
Exceptional
(9 reviews)

Gorgeous Lakeside BarnHOUSE + SAUNA!

Ashland

18% off
$298
$2,088 for 7 nights
All fees included
Gorgeous Lakeside BarnHOUSE + SAUNA!
Private kitchen
Exterior detail
Interior
Property grounds
Exceptional
(5 reviews)

ABBOTT'S COTTAGES- Cardinal cottage. 1 bedroom/1 bath, short walk to downtown!

Ashland

8% off
$146
$1,024 for 7 nights
All fees included
ABBOTT'S COTTAGES- Cardinal cottage. 1 bedroom/1 bath, short walk to downtown!
Room
Outdoor dining
Exterior
Living area
Exceptional
(5 reviews)

ABBOTT'S COTTAGES- The Bluejay. 3 bedroom/2 bath in walking distance to downtown

Ashland

9% off
$295
$2,063 for 7 nights
All fees included
ABBOTT'S COTTAGES- The Bluejay. 3 bedroom/2 bath in walking distance to downtown
Titania kitchen
Oberon
Oberon entry
Property grounds
Exceptional
(136 reviews)

Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland

Ashland

9% off
$186
$1,300 for 7 nights
All fees included
Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
Interior
Private kitchen
Dining
Interior
Exceptional
(8 reviews)

Galaxy-Themed, Fastest WiFi, 3 King Beds Home

Medford

6% off
$231
$1,619 for 7 nights
All fees included
Galaxy-Themed, Fastest WiFi, 3 King Beds Home
Room
Exterior detail
Outdoor dining
Private kitchen
Exceptional
(6 reviews)

ABBOTT'S COTTAGES- The Egret. Studio cottage within walking distance of downtown

Ashland

8% off
$141
$988 for 7 nights
All fees included
ABBOTT'S COTTAGES- The Egret. Studio cottage within walking distance of downtown
Living area
Living area
Exterior detail
Primary bedroom
Exceptional
(53 reviews)

East Main Downtown Bungalow

Ashland

17% off
$147
$1,028 for 7 nights
All fees included
East Main Downtown Bungalow
Dining
Primary bedroom
Exterior detail
Private kitchen
Exceptional
(48 reviews)

New Downtown 3 Bedroom Upstairs Flat with views

Ashland

18% off
$257
$1,800 for 7 nights
All fees included
New Downtown 3 Bedroom Upstairs Flat with views
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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: These spacious homes are the top choice for visitors in Ashland, offering a homey atmosphere perfect for families or groups.
  • Cottages: Quaint and cozy, cottages are a charming option for those seeking a peaceful getaway in Ashland.
  • Apartments: Ideal for solo travelers or couples, apartments provide convenient and comfortable accommodations in the heart of the city.
  • Cabins: 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: 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: 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: 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, savor exquisite wines at Paschal Winery just 5 miles away, or take an adventurous ride on the 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, enjoying its serene atmosphere. For a fun adventure, head to 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 for an evening of culture and entertainment. For adventure lovers, hike the Bull Gap Lower Trailhead and enjoy stunning scenery. Don't miss the 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: 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: 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: 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: 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: 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: 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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January36.3°F (2.4°C)Light RainMostly SunnyAverageSlightly Low
February37.2°F (2.9°C)Light RainMostly SunnyAverageSlightly Low
March40.5°F (4.7°C)Light RainMostly SunnyAverageAverage
April46.0°F (7.8°C)Light RainMostly SunnySlightly HighSlightly Low
May53.2°F (11.8°C)Light RainMostly SunnyAverageAverage
June60.4°F (15.8°C)No Rain (Dry)Mostly SunnySlightly HighSlightly High
July69.3°F (20.7°C)No Rain (Dry)SunnySlightly HighSlightly High
August68.7°F (20.4°C)No Rain (Dry)SunnyAverageSlightly High
September61.5°F (16.4°C)No Rain (Dry)SunnyAverageAverage
October51.1°F (10.6°C)Light RainMostly SunnySlightly LowAverage
November40.8°F (4.9°C)Light RainMostly SunnySlightly LowAverage
December34.7°F (1.5°C)Light RainMostly SunnySlightly LowAverage

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.

In fair Ashland, where we lay our scene...

Best known for its world-class Shakespeare festival, this welcoming city has a super-arty college vibe, and feels smaller than it is, in a good way. An Ashland vacation rental gives you the kind of high culture that leaves the other theatrical hotspots sulking into their interval drinks, but it also does a fine line in brewpubs, quirky eateries, lively nightspots, and intrepid outdoor adventure. Not only that, but folks here are so friendly that you can understand why the thru-hikers from the Pacific Crest Trail are so reluctant to leave. After all, "what is the city but the people?"

Is this a Shakespeare festival I see before me?

In Ashland, "the play's the thing," and the Oregon Shakespeare Festival is an Ashland institution. For the last 80 years, it's been staging the best of the Bard along with up-to-the-minute works from more modern writers. It runs between February and November, putting on a heap of plays across several venues. Less famous, but just as good, is the Ashland Independent Film Festival. And if all that sounds like a bit too much sitting down for you, how about taking a stroll in the city's pride and joy, Lithia Park, or getting hands-on at ScienceWorks museum?

To Ashland or not to Ashland, there is no question

Though a good chunk of vacationers are in town for the theater, Ashland offers plenty of outdoor activities too. It's a much-loved R&R pit-stop on the Pacific Crest Trail, which accounts for the more extreme examples of beards and boots mixed up among the thespians. Water activities feature almost as prominently, especially rafting, kayaking, and fishing on the Rogue River. And when the snow comes, you can be sure that it won't be a winter of discontent for the daring souls shooting down the slopes at Mount Ashland Ski Area.

Shall I compare thee to a summer's day, O Ashland?

A "more lovely and more temperate" choice than an Ashland vacation rental is going to be a tall order. Sure, the odd dump of snow in the winter will leave those mountain tops "whiter than new snow upon a raven's back," and there's the occasional summer day when "too hot the eye of heaven shines," but generally the weather in Ashland is as refined as the city itself. Ashland tends to escape the worst of the North West's famous rain, but as the man himself said, "sometimes hath the brightest day a cloud." So bring a raincoat.

A vacation! A vacation! My kingdom for a vacation!

Thanks to its location in the foothills of the Siskiyou and Cascades mountains, the landscapes round Ashland are nothing short of spectacular. Rushing rivers, vast forests, and snow-capped peaks are the order of the day. To the south, you've got Siskiyou Mountain Park, with Mount Ashland an obvious point. Closer in to Ashland, it's more about the fields and orchards, and after all that nature, you might decide to sample the produce of one of the local vineyards. For as we all know, "good wine is a good familiar creature, if it be well used."

Transportation to and around Ashland

The nearest airport is in Rogue Valley Intl. Airport (MFR), located 14.4 mi (23.3 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Klamath Falls, OR (LMT-Klamath Falls Intl.), which is 49.7 mi (79.9 km) away.

Frequently asked questions

What is the best area to stay in Ashland when booking a vacation rental?
Among the most sought-after neighborhoods to book a vacation property in Ashland is Historic Railroad District. Find your perfect stay with Vrbo and explore this area as a local.
What is the most popular type of vacation rental accommodation in Ashland?
Cabins are the most popular type of vacation rental in Ashland, according to our data. Even if you have something different in mind, Vrbo has properties in loads of sizes and shapes. Explore our options to find your ideal match.
How much does it cost to rent a vacation rental in Ashland?
The average price for a vacation home in Ashland is based on several factors, like property type, length of stay and time of year. Whether you prefer a sprawling villa with space for extended family or a cozy condo ideal for just you and the kids, just add your dates of travel to discover stays that offer great value.
How much does it cost to rent a beach house in Ashland?
Prices for beach houses in Ashland may vary depending on the style and size of the property and when you plan to travel. Simply enter your travel dates into Vrbo and the number of guests to view vacation rental options and prices. From there you can use our filter tool to narrow down your search by amenities, ratings, nearby activities and more.
Are there pet-friendly vacation rentals in Ashland?
With 168 vacation rentals that welcome pets, your furry little friend can join you on your Ashland vacation. Use the filter tool to search our pet-friendly vacation rentals and find the pawfect pad on Vrbo.
Can I rent a house with a pool in Ashland?
Check the "pool" box in our handy filter tool and you'll find 10 houses with private pools in Ashland on Vrbo. Morning dip, sunset soak or midnight swim? How you spend your leisure time is up to you when your Vrbo vacation home comes with its own swimming pool.
What are popular rental amenities in Ashland?
When it comes to rental amenities that guests are on the lookout for in Ashland, an electric car charging station, a barbecue grill and a garden are at the top of the list. With Vrbo vacation homes, you'll enjoy options to match your taste and style, whether you're going on a vacation with friends, relatives or even pets.
Are there large group vacation rentals in Ashland?
Ashland has 20 vacation properties that can accommodate 10 or more people. These stays come with enough space to share good times with friends and family.
Are there vacation rentals in Ashland that welcome kids?
Ashland has 166 family-friendly vacation rentals. And booking a stay that welcomes children is a cinch with our "Properties good for families" filter. On top of having the entire place to yourselves, you can also look forward to conveniences and perks like bunk beds, full kitchens and private pools.
What are the top attractions for families in Ashland?
Keep the kids busy at these leading family-friendly attractions in Ashland:
  • North Mountain Park
  • Mount Ashland Ski Area
  • Emigrant Lake
Are there one-bedroom vacation rentals in Ashland?
You'll find 52 one-bedroom properties in Ashland to pick from. A one-bedroom vacation property is a great choice if it's just two of you or if you're vacationing solo. Add in more space, convenience and privacy than a hotel, and you've got yourself a getaway to remember.
Can I find two-bedroom vacation rentals in Ashland?
Ashland has 50 two-bedroom vacation properties for you to select from. Experience a vacation home with all the space and comfort you need at a price that's hard to resist on Vrbo.
Are there vacation rentals with WiFi in Ashland?
Ashland has 41 vacation rentals with WiFi, so you can stay connected when you're away. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming Hollywood blockbusters to catching up on social media, these Vrbo homes make it a breeze to go online.
How can I find vacation rentals with air conditioning in Ashland?
Pick your dates and then use the filters to locate vacation rentals with ac in Ashland on Vrbo. With 129 air-conditioned properties available here, you can enjoy a cool and comfy stay.
How old do you have to be to rent a vacation rental in Ashland?
The minimum age allowed can differ across properties on Vrbo, so double-check the rules of the vacation rental in Ashland you want to book. But usually, it's 16, 18 or 21.
How long can I rent a vacation rental in Ashland for?
The length of time you can book a vacation rental in Ashland is down to the property. Just enter your chosen dates to display a list of options offering extended stays. With a range of amenities such as full kitchens and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to get the perfect place to call your home away from home in Ashland.
Does Vrbo offer discounts for vacation homes in Ashland?
Short stay or extended escape, Vrbo has some fantastic deals and discounts in Ashland that'll match your style and your budget. Browse our weekly and monthly discounts on vacation rentals, or see what's recently been added with one of our newly listed homes. Whatever you're after, you'll find the ideal place to stay — without breaking the bank.

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