Ashland holiday lettings

We found 299 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.

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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)
  • EdenVale Winery (9.3 mi / 15 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)
  • 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)
  • Hyatt Reservoir (12.9 mi / 20.8 km)
  • TouVelle State Recreation Site (19.1 mi / 30.7 km)
  • Lake of the Woods (28 mi / 45.1 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, a popular area to stay is the downtown district. This vibrant neighbourhood is renowned for its charming atmosphere, with an array of boutique shops, delightful cafes, and restaurants serving up local cuisine. A highlight of this area is the Oregon Shakespeare Festival, which draws theatre enthusiasts from far and wide, offering a rich programme of performances throughout the year.

Another appealing area is the Ashland Creek neighbourhood, which provides a more tranquil setting, ideal for nature lovers. Here, you can enjoy easy access to the stunning trails of Lithia Park, a beautiful expanse of greenery great for leisurely strolls or picnics. This park is also home to the beautiful Japanese Garden and a lovely duck pond, making it a fantastic spot for relaxation and outdoor activities.

Both neighbourhoods have a variety of properties available, ranging from quaint cottages to modern apartments, ensuring that visitors can find accommodation that suits their needs and preferences.
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 those looking for ski resort rentals near Ashland, the closest ski area is Mount Ashland, located just a short drive from the town. In Ashland itself, travellers can find a variety of accommodations, including charming lodges and cosy cabins that cater to both couples and families. Many of these properties come equipped with essential amenities such as fully stocked kitchens, comfortable living spaces, and often stunning views of the surrounding mountains.

In addition to these lodgings, travellers can also explore nearby rental options in the scenic area of Talent, which is just a few miles from Ashland. Here, visitors can find properties that may feature spacious backyards, hot tubs, and easy access to hiking trails, superb for unwinding after a day on the slopes.

Furthermore, Ashland is not just a ski destination; it is also renowned for its vibrant arts scene, particularly the Oregon Shakespeare Festival, which adds cultural richness to the area. Many accommodations in Ashland offer proximity to local shops and restaurants, ensuring a well-rounded experience for those looking to enjoy both winter sports and the local charm.
What is the most popular type of holiday rental accomodation in Ashland?
In Ashland, holiday houses are the most popular type of holiday rental, with approximately 352 available throughout the area. These properties are often situated in charming neighbourhoods close to the Oregon Shakespeare Festival and the beautiful Lithia Park, making them ideal for visitors wanting to explore the local culture and outdoor activities. Most holiday houses come equipped with spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor areas for relaxation, superb for families or larger groups.

Apartments also feature prominently, with around 200 options offering a more compact stay. These typically include essential amenities such as kitchen facilities, comfortable living areas, and sometimes balconies to enjoy the surrounding views. Cottages, numbering about 160, provide a quaint alternative with a homely feel, often set in serene locations that allow for a peaceful retreat.

While cabins and chalets are less common, with around 72 cabins and several chalets available, they offer great experiences for those looking to immerse themselves in nature.
Are there any family house rentals in Ashland?
In Ashland, Oregon, there are a substantial number of family-friendly house rentals available, with around 87 options to choose from. This charming town is renowned for its vibrant arts scene and stunning natural surroundings, making it an excellent choice for family getaways. Properties in the area typically offer spacious living areas, fully equipped kitchens great for preparing family meals, and outdoor spaces where children can play and explore.

Visitors can find homes in various neighbourhoods, such as the historic district, which is close to the renowned Oregon Shakespeare Festival, providing easy access to cultural performances and events. Additionally, many rentals are conveniently located near parks like Lithia Park, where families can enjoy picnics, hiking trails, and playgrounds.
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 and hot tubs, with around 11 options to choose from. This picturesque town, known for its vibrant arts scene and proximity to the stunning Rogue Valley, offers a variety of neighbourhoods where these properties can be found. Many rentals are situated near the beautiful Lithia Park, providing a serene environment for relaxation.

Travellers can expect a range of amenities in these holiday homes, including private pools, hot tubs for unwinding after a day of exploring, and spacious outdoor areas superb for gatherings. Fully equipped kitchens are common, allowing for self-catering, while some properties may also include features such as barbecue grills and fire pits, enhancing the outdoor living 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, with a variety of options suiting different tastes and preferences. Many of these holiday homes feature amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces like patios or gardens where pets can enjoy some fresh air.

The surrounding area is rich in cultural and natural attractions, making it a great destination for travellers with pets. Ashland is home to beautiful parks, including Lithia Park, which offers expansive green spaces, walking trails, and ponds that are superb for leisurely strolls with your furry companions. Additionally, the town is known for its vibrant arts scene, including the renowned Oregon Shakespeare Festival, providing visitors with plenty of entertainment options while enjoying a pet-friendly atmosphere.
Are there any remote work holiday rentals in Ashland?
In Ashland, Oregon, there are numerous remote work-friendly holiday rentals available, with around 648 options to choose from. This charming town is known for its vibrant arts scene and the famous Oregon Shakespeare Festival, making it an appealing destination for those looking to combine work and leisure. Many of the properties come equipped with essential amenities for remote work, such as reliable Wi-Fi access in both public areas and private rooms, ensuring that guests can stay connected while enjoying their surroundings.

Travellers can expect to find a range of accommodations, from cosy cottages to spacious homes, often featuring comfortable workspaces, full kitchens for meal preparation, and inviting outdoor areas for relaxation. Ashland's picturesque landscape, including nearby hiking trails and the scenic Lithia Park, provides ample opportunities for breaks and outdoor activities after work hours. 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 rental amenities include kitchens, allowing guests to prepare their own meals, and onsite parking for convenience. Many properties also feature decks or patios, providing a pleasant outdoor space to relax and enjoy the surroundings. Additionally, a coffee and tea maker is commonly found in rentals, ensuring guests can easily brew their favourite hot beverages. For those travelling with pets, many accommodations in the area permit pets, making it easier for families to bring their furry companions along.
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 summer months of June to August, with July being particularly popular. This peak season draws visitors eager to experience the vibrant setting of the Oregon Shakespeare Festival, which showcases an array of outstanding performances in a beautiful outdoor setting.

With warm temperatures averaging around 25 to 30 degrees Celsius, summer in Ashland is superb for enjoying outdoor activities. The lush landscapes provide a stunning backdrop for hiking, exploring local parks, and participating in various festivals that celebrate the region's rich culture and community spirit.

For those looking for a more budget-friendly option, consider planning your trip in December. Although it's the low season, the winter months offer a serene charm, with the possibility of light snowfall and festive holiday decorations throughout the town. This quieter time allows for a more relaxed exploration of Ashland's local art galleries, quaint shops, and delightful eateries.
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, visitors can engage in a vibrant cultural scene and stunning natural beauty. The Oregon Shakespeare Festival, located in the heart of the town, is a significant draw, showcasing a range of performances throughout the year, attracting theatre enthusiasts from all over. Nearby, Lithia Park offers a picturesque setting with its beautiful gardens, walking paths, and tranquil duck ponds, superb for leisurely strolls or picnics.

The downtown area is filled with charming shops, cafés, and art galleries, allowing visitors to explore local crafts and enjoy a meal or coffee at one of the many inviting spots. For those interested in outdoor activities, the surrounding area provides opportunities for hiking, particularly in the nearby Cascade-Siskiyou National Monument, which boasts scenic trails and breathtaking views.
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 cabin or a beach house, you can turn your space into a standout destination, become a host 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 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 makes organising 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.

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