Ashland holiday lettings

We found 297 holiday rentals — enter your dates for availability

Discover a selection of 104 homes, 57 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

  • 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)
  • EdenVale Winery (9.3 mi / 15 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)
  • Centennial Golf Club (9.4 mi / 15.1 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)
  • Roxy Ann Peak and Prescott Park (11.4 mi / 18.3 km)
  • Howard Prairie Lake (16.1 mi / 26 km)
  • Applegate Lake (24.2 mi / 38.9 km)
  • Lake of the Woods (28 mi / 45.1 km)
  • North Mountain Park (0.7 mi / 1.2 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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