Ashland holiday lettings

We found 284 holiday rentals — enter your dates for availability

Discover a selection of 131 homes, 49 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:7 Nov - 14 Nov

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

Welcome to the Ashland Lavender Estate view from the hot tub
9.8 out of 10 rating
Exceptional
(25 reviews)

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

Ashland, OR

8% off
Price is £4,574
£653 per night
includes taxes & fees
Come stay at our farmhouse! A place to integrate all the beauty surrounding you!

Find spaces that suit your style

  • 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

Find out more about Ashland

Find out more about Ashland

Why visit Ashland

  • Stunning natural landscapes: Ashland boasts breathtaking scenery, including picturesque lakes and nearby mountains, perfect for outdoor enthusiasts.
  • Cultural experiences: Immerse yourself in the local culture by exploring charming streets and vibrant arts scenes.
  • Outdoor activities: Enjoy a range of adventures such as hiking, biking, and relaxing in urban parks.
  • Romantic settings: Stroll through beautiful gardens and enjoy scenic views, ideal for couples seeking a peaceful getaway.
  • Diverse accommodation options: Choose from charming cottages, stylish apartments, or private holiday homes for a comfortable stay.

Popular types of accommodation in Ashland

You’ve chosen Ashland for your next getaway, and now it’s time to find the perfect place to stay. Explore a variety of popular accommodation options, including houses, charming cottages, and stylish apartments. Our comprehensive rental listings in Ashland ensure you find the ideal rental property to suit your needs, providing transparency and peace of mind for your holiday.

  • Houses: The most sought-after accommodation in Ashland, offering spacious and comfortable living for families, couples, or groups.
  • Cottages: Charming and cosy, these quaint retreats provide a delightful stay, perfect for a peaceful getaway.
  • Apartments: Ideal for those seeking convenience, these self-contained units offer a home-like atmosphere while exploring the area.
  • Cabins: Rustic and inviting, cabins provide a unique experience, often nestled in nature, perfect for a relaxing stay.
  • Chalets: These alpine-style lodgings offer a blend of comfort and charm, ideal for a picturesque retreat.**

Top attractions in Ashland

Ashland is a delightful destination for those seeking outdoor adventures and scenic beauty. With its picturesque lakes, modern colleges, and urban parks, the area offers a variety of attractions for travellers looking to immerse themselves in nature and enjoy a beach experience. Whether you're hiking, exploring the local culture, or simply relaxing in the great outdoors, Ashland promises a memorable holiday for all visitors.

  • Southern Oregon University: This modern university offers a vibrant atmosphere, with beautiful campus grounds and a blend of academic and cultural events. Visitors can enjoy the lively city vibes and explore various art installations.
  • Lithia Park: A picturesque urban park featuring lush gardens, walking trails, and playgrounds, perfect for families. Enjoy outdoor activities amid its serene setting, ideal for picnics and leisurely strolls.
  • Howard Prairie Lake: A stunning lake surrounded by breathtaking scenery, perfect for a romantic getaway. Enjoy beach activities, fishing, and picturesque views that create a tranquil outdoor experience.

Things to do recommended for couples

For a romantic escape in Ashland, indulge in skiing at Mount Ashland Ski Area or take an adventurous ride on the Windsor Ski Lift. Don’t miss a delightful visit to Paschal Winery, just 3.1km away, where you can savour fine wines in an enchanting setting.

Things to do recommended for families

Your family will delight in the wellness vibes at Lithia & Driveway Fields, only 6.2km from Ashland. For adventure, visit the Rogue Valley Family Fun Center, 9.9km away, or unwind at the nearby Howard Prairie County Resort, offering relaxation for all ages.

Things to do recommended for groups

Groups visiting Ashland can immerse themselves in the vibrant performances at the Oregon Shakespeare Festival, browse local crafts at the Lithia Artisans Market, and embark on an adventurous hike along the Bull Gap Lower Trailhead, enjoying the area's stunning scenery and outdoor charm.

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

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

  • Traveling to Ashland with a group: Think about how many bedrooms you’ll require, as well as features like a fully-equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily apply filters for all these options and more on Vrbo.
  • Traveling to Ashland with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, as well as ensure access to suitable amenities like a private swimming pool. Additionally, it's wise to take into account your closeness to family-friendly attractions.
  • Taking your pets with you to Ashland: For many, a family holiday wouldn’t be the same without their four-legged companion. 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 offers for stays of a month or more, you’ve come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly accommodations. Don’t forget to include options like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay in and around Ashland

Ashland, Oregon, is a charming destination perfect for outdoor enthusiasts and adventure seekers. Nestled in stunning scenery, this friendly city offers a variety of experiences, from romantic strolls to family outings. Nearby attractions provide ample opportunities for exploration, whether you're hiking in the picturesque mountains or enjoying local culture. Don't miss the Ashland Oregon Chamber for insights on the best places to visit and things to do in this delightful region.

  • Historic Downtown District: The Historic Downtown District in Ashland is a charming area that perfectly blends history with modern-day culture. Known for its romantic ambience, it's an excellent spot for families and outdoor enthusiasts alike. The district boasts various theatres, including the renowned Oregon Shakespeare Festival, and offers educational experiences through local museums. Nature lovers will appreciate the nearby lake and access to the stunning national and state parks, perfect for hiking and leisurely strolls. This vibrant neighbourhood is ideal for those looking to immerse themselves in Ashland's artistic and natural beauty.
  • Talent: Located a mere 3.1km from Ashland, the city of Talent is a hidden gem for those seeking adventure and picturesque scenery. This area is characterised by its outdoor recreational spaces, making it a favourite for hiking, cycling, and even skiing in the winter months. The local theatres provide a dose of culture, while the beautiful lakes and national parks nearby offer endless opportunities for exploration. Talent is a delightful destination for those wanting to indulge in nature while enjoying the charm of a small-town atmosphere.
  • Historic Railroad District: The Historic Railroad District, also in close proximity to Ashland, is a delightful neighbourhood that caters to families, couples, and outdoor adventurers. This area is steeped in history and features charming buildings that tell the story of the past. Visitors can explore local theatres and enjoy scenic hiking trails, while skiing at nearby resorts adds to the adventure. With a beautiful lake and access to magnificent national and state parks, this district is a fantastic spot for those seeking both excitement and relaxation in a picturesque 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.

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 a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate quite a bit. Moreover, opting for a longer stay often results in significant savings. To discover the ideal Vrbo property that suits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new journeys, pick up where you left off, or manage your travel arrangements. You can easily access the properties you've saved and booked, now organised under Potential, Upcoming, or Current Trips. To start using 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)
  • StoneRiver Vineyards (7.5 mi / 12.1 km)
  • EdenVale Winery (9.3 mi / 15 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)
  • Applegate Lake (24.2 mi / 38.9 km)
  • North Mountain Park (0.7 mi / 1.2 km)
  • Roxy Ann Peak and Prescott Park (11.4 mi / 18.3 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?
When considering a holiday rental in Ashland, Oregon, the Historic Downtown area is an excellent choice. This charming neighbourhood is not only picturesque but also vibrant, with a variety of shops, cafes, and restaurants lining its streets. Staying here puts you within easy reach of the renowned Oregon Shakespeare Festival, which draws visitors from around the world for its outstanding theatrical performances. Additionally, the beautiful Lithia Park, with its serene landscapes and walking trails, offers a great spot for relaxation and leisure.

Another appealing area is the Ashland Creek neighbourhood, which provides a more tranquil setting while still being conveniently close to the downtown attractions. This peaceful enclave features lovely homes and is just a short stroll from the park and theatre district. With a blend of nature and culture, it's an ideal location for those who appreciate a quieter atmosphere while still wanting to partake in the local festivities.
How much does it cost to rent a holiday home in Ashland?
Prices for holiday 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 to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Ashland holiday 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 ski resort rentals near Ashland, Oregon, the most top option is the Mount Ashland Ski Area, which is located approximately 20 miles from the town. Visitors looking for accommodations can explore options in Ashland itself, where a variety of properties cater to different needs. Many holiday rentals in the area include charming cottages and modern apartments, often featuring amenities such as full kitchens, fireplaces, and outdoor spaces to relax after a day on the slopes.

In Ashland, guests can enjoy the vibrant arts scene, with easy access to the Oregon Shakespeare Festival and an array of local shops and restaurants. Properties tend to be well-equipped for both comfort and convenience, with many offering Wi-Fi and laundry facilities. Those who prefer a more rustic experience can consider cabins and lodges located slightly further afield, which may provide stunning views of the surrounding mountains and additional amenities like hot tubs or game rooms.
What is the most popular type of holiday rental accomodation in Ashland?
In Ashland, holiday houses are the most popular type of accommodation, with around 123 available throughout the area. These holiday houses often feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces such as decks or gardens, making them ideal for families or groups. Additionally, there are approximately 42 apartments, which tend to be located closer to the town centre, providing easy access to local shops, restaurants, and the renowned Oregon Shakespeare Festival. These apartments typically come with modern amenities, such as kitchen facilities and comfortable living areas. Cottages, numbering around 36, offer a charming, rustic experience, often located in scenic locations, while there are also about 19 cabins available for those seeking a more secluded retreat in the surrounding nature.
Are there any family house rentals in Ashland?
In Ashland, Oregon, there is a wealth of family-friendly holiday rentals available—over one hundred in total. This charming town is renowned for its vibrant arts scene and the famous Oregon Shakespeare Festival, making it an ideal getaway for families. Many properties offer spacious living areas, well-equipped kitchens for preparing meals together, and outdoor spaces great for children to play.

Families can also enjoy amenities such as Wi-Fi, laundry facilities, and some homes even feature private gardens or patios for relaxation after a day of exploring. The historic downtown area, with its eclectic boutiques and eateries, is within easy reach, providing an excellent opportunity for families to experience local culture and cuisine.
Can I rent a holiday home with a pool or hot tub in Ashland?
In Ashland, there are several holiday homes available for rent that feature pools or hot tubs, making it an excellent choice for travellers seeking relaxation and leisure. This charming town, known for its vibrant arts scene and proximity to the stunning landscapes of Southern Oregon, offers a variety of neighbourhoods where these properties can be found.

Many of the rentals come equipped with private pools or hot tubs, outdoor living spaces, and fully equipped kitchens, ideal for both unwinding after a day of exploring and hosting family gatherings. Some properties may also offer additional amenities such as expansive gardens, fire pits, and scenic views of the surrounding mountains, enhancing the overall experience.
Can I find long-stay holiday rentals in Ashland?
A long-stay holiday rental in Ashland is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Ashland?
In Ashland, there are numerous pet-friendly house rentals available, providing a welcoming environment for travellers with pets. Many of these properties feature convenient amenities such as fully equipped kitchens, outdoor spaces, and comfortable living areas, ideal for families or groups.

The neighbourhoods around Ashland are rich in natural beauty and cultural experiences. For instance, homes near Lithia Park offer beautiful surroundings, with easy access to walking trails and lush gardens, superb for leisurely strolls with pets. Additionally, the area is known for its vibrant arts scene, including the renowned Oregon Shakespeare Festival, which adds to the overall charm of the town.
Are there any remote work holiday rentals in Ashland?
In Ashland, Oregon, there is a substantial selection of remote work holiday rentals available, with around 178 properties to choose from. This vibrant town is not only known for its stunning natural beauty but also for its cultural offerings, including the renowned Oregon Shakespeare Festival. Many of the rentals cater specifically to remote workers, providing amenities such as dedicated office spaces, desks, ergonomic chairs, and high-speed Wi-Fi, ensuring a productive environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Ashland holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Ashland with parking available—perfect for families or travellers 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 holiday rental amenities typically include fully equipped kitchens, which allow guests to prepare their own meals with ease. Many rentals feature essential appliances such as microwaves and refrigerators, along with cookware, dishware, and utensils to enhance the self-catering experience. This makes it convenient for travellers to enjoy home-cooked meals while exploring the charming town, known for its vibrant arts scene and the famous Oregon Shakespeare Festival.
When is the best time to visit Ashland for a holiday rental?
The best time to visit Ashland for a holiday rental is during the vibrant summer months, particularly July. This peak season attracts a diverse array of visitors, eager to immerse themselves in the rich cultural offerings and stunning natural beauty of the area. With warm temperatures averaging around 25°C, it's superb for outdoor activities, including hiking the scenic trails or enjoying a leisurely stroll through Lithia Park, known for its lush gardens and inclusive setting.

During this time, Ashland comes alive with the famous Oregon Shakespeare Festival, where theatre enthusiasts can catch a variety of performances in an enchanting setting. The energy in the town is palpable, making it a fantastic option for travellers who appreciate a lively environment filled with artistic expression and community events.

For those looking to save a bit while still enjoying Ashland's charm, consider planning your visit in December. While this month falls into the low season, it offers a great experience with fewer crowds, allowing for a more relaxed exploration of the town's quaint shops and local eateries. Plus, the festive atmosphere during the holiday season adds a lovely touch to a winter getaway.
How early should I book a Ashland holiday rental?
Book your Ashland holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Ashland?
In Ashland, Oregon, visitors can enjoy a variety of attractions that highlight the town's unique charm and cultural offerings. The Oregon Shakespeare Festival, held in the downtown area, is a major draw, attracting theatre lovers from around the globe with its diverse array of performances throughout the year. The vibrant streets of Ashland are lined with quaint shops, art galleries, and cafes, creating a lively atmosphere for strolling and exploring.

For nature enthusiasts, Lithia Park offers expansive green spaces, walking trails, and picturesque duck ponds, providing a serene escape right in the heart of the town. The park's beautiful landscaping and stunning views of the surrounding mountains make it a great spot for a leisurely picnic or an afternoon of relaxation.
Can I change or cancel my Ashland home rental booking on Vrbo?
To find Ashland holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" 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 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 travellers 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 cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Ashland holiday 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.

Explore destinations around Ashland

More Holiday Rentals ideas

Bay City Holiday Rentals
Standard Link for Bay City
Cannon Beach Holiday Rentals
Standard Link for Cannon Beach
Crater Lake Holiday Rentals
Standard Link for Crater Lake
Waldport Holiday Rentals
Standard Link for Waldport
Depoe Bay Holiday Rentals
Standard Link for Depoe Bay
Lincoln City Holiday Rentals
Standard Link for Lincoln City
Tillamook Holiday Rentals
Standard Link for Tillamook
Grants Pass Holiday Rentals
Standard Link for Grants Pass
Bandon Holiday Rentals
Standard Link for Bandon
Newport Holiday Rentals
Standard Link for Newport
St. Helens Holiday Rentals
Standard Link for St. Helens
Rockaway Beach Holiday Rentals
Standard Link for Rockaway Beach
Cloverdale Holiday Rentals
Standard Link for Cloverdale
Hillsboro Holiday Rentals
Standard Link for Hillsboro
Brookings Holiday Rentals
Standard Link for Brookings
Mount Hood Holiday Rentals
Standard Link for Mount Hood
Prospect Holiday Rentals
Standard Link for Prospect
Mount Angel Holiday Rentals
Standard Link for Mount Angel
Florence Holiday Rentals
Standard Link for Florence
Medford Holiday Rentals
Standard Link for Medford
Port Orford Holiday Rentals
Standard Link for Port Orford
Manzanita Holiday Rentals
Standard Link for Manzanita
Astoria Holiday Rentals
Standard Link for Astoria
Pacific City Holiday Rentals
Standard Link for Pacific City
Hood River Holiday Rentals
Standard Link for Hood River
Seal Rock Holiday Rentals
Standard Link for Seal Rock
Bend Holiday Rentals
Standard Link for Bend
Seaside Holiday Rentals
Standard Link for Seaside
Government Camp Holiday Rentals
Standard Link for Government Camp

People also search for

Pet-friendly holiday rentals in Lincoln City
Standard Link for Lincoln City