Ashland holiday lettings

We found 289 holiday rentals — enter your dates for availability
Discover a selection of 107 homes, 56 apartments and other holiday rentals in Ashland that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday homes have the best amenities for spending time at your holiday home, which might include parking and a garden. Whatever you're looking for, you're sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Ashland

Showing deals for:11 Dec - 18 Dec

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

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

Ashland

8% off
£4,553
for 7 nights, 1 room
£650 per night
includes taxes & fees
Come stay at our farmhouse! A place to integrate all the beauty surrounding you!
Kitchen
Kitchen
Exterior
Double Rainbow
Exceptional
(131 reviews)

Tranquil setting surrounded by panoramic mountain views, grazing horses

Phoenix

11% off
£746
for 7 nights, 1 cottage
£107 per night
includes taxes & fees
Tranquil setting surrounded by panoramic mountain views, grazing horses
Private kitchen
Private kitchen
Room
Interior
Wonderful
(9 reviews)

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

Ashland

15% off
£1,053
for 7 nights, 1 home
£150 per night
includes taxes & fees
Beautiful bungalow downtown Ashland railroad district, rv parking, adventure!
Room
Exterior
Private kitchen
Living area
Exceptional
(82 reviews)

Premier Downstairs Flat in Perfect Down Town Location

Ashland

16% off
£1,479
for 7 nights, 1 home
£211 per night
includes taxes & fees
Premier Downstairs Flat in Perfect Down Town Location
Your friendly host(s) are often in the small cabin in case you need anything. :)
Dining
Living area
Living area
Exceptional
(9 reviews)

Gorgeous Lakeside BarnHOUSE + SAUNA!

Ashland

18% off
£1,506
for 7 nights, 1 home
£215 per night
includes taxes & fees
Gorgeous Lakeside BarnHOUSE + SAUNA!
Private kitchen
Exterior detail
Property grounds
Interior
Exceptional
(5 reviews)

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

Ashland

8% off
£829
for 7 nights, 1 cottage
£118 per night
includes taxes & fees
ABBOTT'S COTTAGES- Cardinal cottage. 1 bedroom/1 bath, short walk to downtown!
Living area
Outdoor dining
Room
Exterior
Exceptional
(5 reviews)

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

Ashland

8% off
£1,696
for 7 nights, 1 home
£242 per night
includes taxes & fees
ABBOTT'S COTTAGES- The Bluejay. 3 bedroom/2 bath in walking distance to downtown
Titania kitchen
Oberon
Property grounds
Titania kitchen
Exceptional
(136 reviews)

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

Ashland

8% off
£1,080
for 7 nights, 1 apartment
£154 per night
includes taxes & fees
Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
Interior
Private kitchen
Interior
Dining
Exceptional
(8 reviews)

Galaxy-Themed, Fastest WiFi, 3 King Beds Home

Medford

6% off
£1,371
for 7 nights, 1 home
£196 per night
includes taxes & fees
Galaxy-Themed, Fastest WiFi, 3 King Beds Home
Private kitchen
Exterior detail
Living area
Room
Exceptional
(6 reviews)

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

Ashland

8% off
£801
for 7 nights, 1 apartment
£114 per night
includes taxes & fees
ABBOTT'S COTTAGES- The Egret. Studio cottage within walking distance of downtown
Exterior detail
Living area
Living area
Interior
Exceptional
(53 reviews)

East Main Downtown Bungalow

Ashland

16% off
£833
for 7 nights, 1 home
£119 per night
includes taxes & fees
East Main Downtown Bungalow
Living area
Primary bedroom
Exterior detail
Private kitchen
Exceptional
(48 reviews)

New Downtown 3 Bedroom Upstairs Flat with views

Ashland

16% off
£1,517
for 7 nights, 1 home
£217 per night
includes taxes & fees
New Downtown 3 Bedroom Upstairs Flat with views
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Ashland

  • Oregon Shakespeare Festival: Experience world-class theatre at this renowned festival, showcasing a variety of plays in a stunning outdoor setting.
  • Scenic Outdoor Activities: Enjoy hiking and exploring the beautiful landscapes that surround Ashland, perfect for nature lovers.
  • Charming Parks: Relax in picturesque parks and gardens that offer serene escapes and family-friendly environments.
  • Local Arts Scene: Immerse yourself in Ashland's vibrant cultural atmosphere with galleries, concerts, and local events.
  • Community Vibes: Experience the friendly, welcoming atmosphere that makes Ashland feel like a home away from home.

Popular types of accommodation in Ashland

Discover the charm of Ashland, Oregon, a captivating city renowned for its vibrant arts scene and stunning natural beauty. From houses and cosy cottages to stylish apartments, there’s a perfect retreat for every traveller. Explore the enchanting landscapes, enjoy scenic hikes, or relax by an onsite pool after a day of adventure. Ashland promises an unforgettable experience with its welcoming atmosphere and rich cultural offerings.

  • Houses: The top choice for visitors, these spacious homes offer a comfortable and private stay in Ashland.
  • Cottages: Quaint and charming, these small homes provide a cozy retreat amidst the lovely surroundings of Ashland.
  • Apartments: Ideal for those seeking convenience, these self-contained units are perfectly situated for easy access to local attractions.
  • Cabins: Embrace nature in these rustic lodgings, offering a serene escape within Ashland's beautiful landscapes.
  • Chalets: These stylish mountain lodges provide a unique blend of comfort and character, perfect for a memorable stay.**

Top attractions in Ashland

Ashland, Oregon, is a charming city perfect for outdoor enthusiasts and those seeking scenic beauty. Visitors can enjoy leisurely walks along Ashland Creek, attend concerts by the Ashland City Band, and experience the renowned Oregon Shakespeare Festival. With its picturesque parks and vibrant cultural scene, Ashland offers a delightful blend of adventure and relaxation, making it an ideal destination for a memorable vacation.

  • Howard Prairie Lake: A serene retreat with picturesque beaches and stunning scenery, perfect for relaxation and romantic outings. Enjoy outdoor activities like fishing and kayaking amidst the tranquil surroundings.
  • Emigrant Lake: Another beautiful lake offering scenic views and a lovely beach atmosphere. Ideal for picnics, swimming, and exploring nature, this spot is perfect for couples and families alike.
  • Lithia Park: An urban oasis featuring lush gardens, walking trails, and playgrounds. A family-friendly environment where you can enjoy outdoor activities while being close to the city’s vibrant culture.

Things to do recommended for couples

For a romantic getaway in Ashland, indulge in a scenic hike at Lithia Park, followed by a picnic amidst the stunning gardens. In the evening, enjoy a captivating performance at the Oregon Shakespeare Festival, creating unforgettable memories together.

Things to do recommended for families

Families visiting Ashland can explore the enchanting Lithia Park, with its lovely playgrounds and duck ponds, and enjoy a thrilling performance at the Oregon Shakespeare Festival, perfect for all ages. Don’t miss the hands-on activities at the ScienceWorks Museum for an educational day out.

Things to do recommended for groups

Experience the thrill of motor racing at Champion Raceway, located 26km from Ashland. It’s the perfect spot for adventure-seeking groups, offering an exhilarating atmosphere filled with excitement and competition.

*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

When planning your trip, whether you're travelling with a group, family, pets, or seeking extended stays, it’s important to filter your options according to your priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Ashland with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor space for group gatherings. Luckily, you can easily filter for all these options, and much more, on Vrbo.
  • Traveling to Ashland with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, along with suitable facilities 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, a family holiday wouldn't feel complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Ashland: If you're in search of holiday rentals with discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Ashland

Ashland, Oregon, offers a delightful blend of outdoor adventures and charming scenery. Visitors can explore the stunning landscapes surrounding the city, enjoy friendly local vibes, and immerse themselves in the vibrant arts scene. Don't miss the picturesque parks and gardens that provide a serene escape, making Ashland a perfect destination for romantic getaways or family outings. Whether hiking in the hills or enjoying a leisurely stroll through the town, Ashland promises an unforgettable holiday experience.

  • Historic Downtown District: Nestled in the heart of Ashland, the Historic Downtown District is a vibrant neighbourhood that perfectly embodies the town's artistic spirit. Renowned for its romantic ambiance, it offers an array of outdoor activities, making it ideal for families and couples alike. Visitors can explore the renowned Oregon Shakespeare Festival, indulge in eclectic dining options, and stroll through charming streets lined with historical buildings. The nearby Lithia Park, with its scenic trails and picturesque lake, provides ample opportunities for hiking and relaxation, while the proximity to both a national park and state park ensures a wealth of natural beauty to discover.
  • Talent: Located a mere 8km from Ashland, the city of Talent is a hidden gem for outdoor enthusiasts seeking adventure and stunning scenery. This quaint town is surrounded by lush landscapes and offers a variety of recreational areas perfect for hiking and exploration. The local theatre scene adds a cultural touch, while the nearby river and state park provide ample opportunities for fishing, kayaking, and peaceful picnics by the water. Talent serves as a serene escape from the bustle of city life, inviting visitors to immerse themselves in the beauty of southern Oregon.
  • Historic Railroad District: The Historic Railroad District, situated close to Ashland, is known for its picturesque scenery and romantic vibes. This charming neighbourhood boasts a unique blend of outdoor activities and cultural attractions. Visitors can enjoy scenic hikes along the nearby trails, visit local theatres, and partake in educational experiences at various venues. The area's proximity to both a national park and state park, along with beautiful lakes, makes it a haven for nature lovers and those seeking a peaceful retreat in a captivating setting.

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 iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 save on your next holiday? Being flexible with your travel dates can really help, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your travels. You can start new trips, pick up from where you last stopped, or easily view and organise your existing plans. Properties you've previously saved or booked are now neatly categorised under Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

The captivating area of Ashland awaits your stay

Enjoy the area's entertainment, theatre scene and opera with a rental holiday home in Ashland. Travellers to this welcoming city praise the festivals, gardens and cafes. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Ashland

Do you want to discover things to do in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Ashland a fun place to get away to. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Mount Ashland Ski Area (7.8 mi / 12.5 km)
  • Centennial Golf Club (9.4 mi / 15.1 km)
  • Rogue Valley Country Club (10.6 mi / 17.1 km)
  • Paschal Winery (5 mi / 8.1 km)
  • EdenVale Winery (9.3 mi / 15 km)
  • Rogue Creamery (16.3 mi / 26.2 km)

Exploring the gardens and other natural features in Ashland

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Ashland is a great place to get outside. These are some of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Lithia Park (0.5 mi / 0.9 km)
  • Emigrant Lake (6.3 mi / 10.2 km)
  • Howard Prairie Lake (16.1 mi / 26 km)
  • Lake of the Woods (28 mi / 45.1 km)
  • North Mountain Park (0.7 mi / 1.2 km)
  • Bull Gap Lower Trailhead (7.1 mi / 11.5 km)

Transport to and around Ashland

The nearest airport is in Medford, OR (MFR-Rogue Valley Intl.), located 14.4 mi (23.3 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to 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 holiday rental?
Historic Railroad District is one of the most sought-after neighbourhoods to book a holiday property in Ashland. Stay here to enjoy the convenience and privacy that comes with having the whole place to yourself.
What is the most popular type of holiday rental accommodation in Ashland?
Houses are the most popular kind of holiday rental in Ashland, according to our data. Even if you have a different vision in mind, Vrbo has properties in many sizes and shapes. Explore our options to find your perfect match.
How much does it cost to rent a holiday rental in Ashland?
Property type, season and length of stay are some factors that can determine the price of a holiday home. Simply add your travel dates to find your dream escape. From quaint country cottages to plush villas, all Vrbo holiday rentals provide amazing value.
How much does it cost to rent a beach house in Ashland?
Prices for beach houses in Ashland may vary depending on the size and style of the property and when you plan to travel. Simply enter your travel dates into Vrbo and the number of guests to see your options and prices. From there you can use our filter tool to refine your search results by ratings, nearby activities, amenities and more.
Are there pet-friendly holiday rentals in Ashland?
Yes, there are. You'll find 59 holiday homes that welcome pets in Ashland on Vrbo. Our furry friends need a break too, so simply use our search function for pet-friendly holiday rentals to find a property where Spot can lap up the good times.
What are popular rental amenities in Ashland?
Tennis, a barbecue grill and a firepit rank as the most popular rental amenities in Ashland. Whether you're planning to travel alone, with your sweetheart or a group of best friends, Vrbo will help you find a holiday rental that matches your tastes with all the features you'll enjoy.
Are there large group holiday rentals in Ashland?
Ashland has seven holiday rentals that can host 10 or more guests. These properties come with all the space you need to share good times with your favourite people.
Are there holiday rentals in Ashland that welcome kids?
With 59 family-friendly holiday homes to choose from in Ashland, now is the perfect time to introduce the kids to the wonders of travel. Simply click on our "Properties good for families" filter box to look for stays that feature conveniences perfect for holidaying families, like living rooms, yards, entertainment units and bunk beds.
What are the top attractions for families in Ashland?
Keep the kids entertained at these leading family-friendly attractions in Ashland:
  • ScienceWorks Hands-On Museum
  • Emigrant Lake
  • Bull Gap Lower Trailhead
Are there one-bedroom holiday rentals in Ashland?
Yes, there are 28 one-bedroom properties in Ashland to select from. A one-bedroom holiday home is a great choice if it's just the two of you or if you're flying solo. Toss in more space, convenience and privacy than a standard hotel, and you're sure to have an unforgettable getaway.
Can I find two-bedroom holiday rentals in Ashland?
Ashland has 12 two-bedroom holiday rentals to choose from. Find a holiday home with all the space and privacy you're looking for at a price that won't break the bank on Vrbo.
Are there holiday rentals with WiFi in Ashland?
Ashland has nine holiday rentals with WiFi, so you'll be able to stay connected during your holiday. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with the family to scrolling social media, these Vrbo homes make it easy to go online.
How can I find holiday rentals with air conditioning in Ashland?
Decide on your travel dates and then use our filters to look for holiday rentals with ac in Ashland on Vrbo. With 56 air-conditioned properties on offer here, you can look forward to a cool and comfortable trip.
How old do you have to be to rent a holiday rental in Ashland?
The minimum age is generally 16, 18 or 21. It can differ between properties on Vrbo, so check the rules of your preferred Ashland holiday rental before booking.
How long can I rent a holiday rental in Ashland for?
It all depends on the Ashland property. To see a list of options offering extended stays, just type your dates and number of guests into the Vrbo search page. Enjoy having the place to yourself, along with comforts such as air conditioning, a kitchen and a yard to run around in. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.

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