Ashland vacation rentals

We found 300 vacation rentals — enter your dates for availability

Discover a selection of 103 homes, 59 apartments, and other vacation rentals in Ashland that are perfect for your trip. Whether you're traveling with a group or just with your pet, vacation homes have the amenities you need and want for your stay, which might include WiFi and a washer and dryer. No matter what you're looking for, you'll find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Ashland

Showing deals for:Mar 20 - Mar 27

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, Exceptional, (29 reviews)
Exceptional
(29 reviews)

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

Ashland

10% off
Price is CA $989
CA $8,138 total
includes taxes & fees
Come stay at our farmhouse! A place to integrate all the beauty surrounding you!

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Find out more about Ashland

Why visit Ashland

  • Stunning outdoor adventures: Ashland is perfect for hiking, biking, and exploring its beautiful parks and trails.
  • Vibrant downtown: Experience a lively atmosphere with quaint shops and diverse eateries in the heart of the city.
  • Cultural events: Attend various festivals and performances, including the renowned Oregon Shakespeare Festival.
  • Scenic beauty: Enjoy picturesque lakes and landscapes that offer a serene escape from everyday life.
  • Diverse accommodation: Choose from charming vacation rentals, cozy cottages, and modern hotels for your stay.

Popular types of accommodation in Ashland

Discover the charm of Ashland with a variety of vacation rentals to suit your needs. From houses and cozy cottages to modern apartments, there's something for everyone. Whether you're seeking a family getaway or a romantic retreat, Ashland vacation rentals offer comfort and convenience. Don't forget to check out the Ashland Hills Hotel for additional options. Your perfect escape awaits.

  • Houses: The top choice for visitors to Ashland, these homes offer ample space and a personal touch, ideal for families or groups.
  • Cottages: A delightful option that combines charm and comfort, perfect for a peaceful getaway.
  • Apartments: Convenient and versatile, these rentals provide a home-like atmosphere right in the heart of Ashland.
  • Cabins: Rustic and cozy, these retreats are perfect for those looking to connect with nature.
  • Chalets: These alpine-style homes offer a unique stay, blending comfort with stunning views.**

Top attractions in Ashland

Ashland, Oregon, is a fantastic destination for outdoor enthusiasts and those seeking scenic beauty. Known for its stunning lakes, vibrant urban parks, and modern educational institutions, this charming city offers a variety of activities for travellers looking to immerse themselves in culture and adventure. Whether you're exploring the natural landscape or enjoying local attractions, Ashland promises a memorable vacation experience.

  • Southern Oregon University: Experience a vibrant campus atmosphere with modern architecture and student life. Engage with local culture through art exhibits and events, making it a lively stop for those interested in education and community.
  • Lithia Park: Enjoy this family-friendly urban park featuring beautiful gardens, walking paths, and play areas. It’s perfect for outdoor activities, picnics, and relaxing in a serene setting while taking in the city vibe.
  • Howard Prairie Lake: Discover a stunning lake retreat ideal for romantic outings. Enjoy breathtaking scenery, sandy beaches, and various outdoor activities like fishing, hiking, or simply soaking in the natural beauty.

Things to do recommended for couples

For a romantic getaway in Ashland, hit the slopes at Mount Ashland Ski Area or take an adventurous ride on the Comer Ski Lift. Afterward, indulge in the charm of EdenVale Winery, just 14.5km away, where you can enjoy fine wines in a romantic setting.

Things to do recommended for families

Your family will love the serene atmosphere at Howard Prairie County Resort and the exciting arcade adventures at Rogue Valley Family Fun Center, located 25.7km from Ashland. Enjoy wellness and relaxation at Howard Prairie County Recreation Area, perfect for making lasting memories together.

Things to do recommended for groups

Experience the vibrant Oregon Shakespeare Festival for a night of culture and entertainment. Enjoy a round of golf at Centennial Golf Club, set in beautiful outdoor surroundings. For shopping and family fun, visit the Rogue Valley Mall, where you can explore various shops and eateries.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're planning a trip with a group, family, pets, or seeking longer stays, it's important to prioritize your filters effectively. Here are some helpful Vrbo booking tips for you.

  • Traveling to Ashland with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Ashland with young kids: Traveling with young children can present its challenges. It's important to prioritize their comfort and safety, along with suitable amenities 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 vacation isn’t truly fulfilling without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Many of these 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 vacation rentals with special offers for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding amenities like a parking space, a well-equipped kitchen, or a private pool to your search as well.

Where to stay in and around Ashland

Ashland, Oregon, is a delightful destination that offers stunning outdoor adventures and charming scenery. With its friendly atmosphere, you can explore vibrant downtown Ashland, where quaint shops and eateries await. Just a short walk from downtown, you’ll find beautiful parks and trails perfect for family outings or romantic strolls. Whether you're hiking, attending a festival, or simply soaking in the natural beauty, Ashland promises a memorable vacation experience that caters to all types of travellers.

  • Historic Downtown District: The Historic Downtown District is the vibrant heart of Ashland, where charming storefronts and cultural experiences come together. This area is perfect for a romantic stroll or a family outing, featuring a variety of shops, restaurants, and art galleries. Visitors can immerse themselves in the local arts scene, with the renowned Oregon Shakespeare Festival taking centre stage. Outdoor enthusiasts will appreciate the nearby hiking trails and the stunning landscapes of the surrounding national parks and lakes, which offer a perfect backdrop for exploration and relaxation.
  • Talent: Located a mere 8.0km from Ashland, Talent is a quaint city known for its breathtaking scenery and adventurous spirit. Outdoor lovers can enjoy a wide range of recreational activities, including hiking, biking, and skiing in winter months. The local theatre scene adds a cultural flair, providing entertainment for visitors of all ages. With its proximity to beautiful lakes and national parks, Talent is an ideal spot for those looking to connect with nature while enjoying a laid-back atmosphere.
  • Historic Railroad District: This charming neighborhood near Ashland is a delightful blend of history and outdoor adventure. The Historic Railroad District is perfect for families and couples alike, offering easy access to theatre productions, scenic hiking trails, and ski resorts during the winter. The area is surrounded by stunning landscapes, including local lakes and national parks, making it an excellent base for outdoor activities. This district's unique architecture and community spirit create a warm and welcoming atmosphere for all visitors.

Best time to go to Ashland

If you're planning a trip to Ashland, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and June to July, while off-peak times, like October to December tend to have fewer bookings and better deals.

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

Booking with Vrbo is simple

Looking to save on your next adventure? Consider being flexible with your travel dates, as prices can fluctuate. Also, extending your stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new trips, pick up right where you left off, or manage and review your travel arrangements. You can easily access properties you've saved and booked, now organized into Potential, Upcoming, or Current Trips. To start using Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

The captivating area of Ashland awaits your stay

Enjoy the area's entertainment, theater scene and opera and make a vacation rental your home during your stay in Ashland. Travelers 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 find top things to see and do in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Ashland a fun spot to vacation. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Stewart Meadows Golf Course (11.2 mi / 18 km)

Exploring the gardens and other natural features in Ashland

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Ashland is a great spot to appreciate mother nature. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • 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)

Transportation to and around Ashland

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

Frequently asked questions

What is the best area to stay in Ashland when booking a vacation rental?
When planning a vacation rental in Ashland, Oregon, one of the best areas to consider is the charming downtown district. This vibrant neighbourhood is known for its lively atmosphere, with a plethora of boutique shops, art galleries, and delightful cafés. Staying here means you'll be just a short stroll away from the renowned Oregon Shakespeare Festival, a top attraction that draws theatre enthusiasts from far and wide. The downtown area also provides easy access to the beautiful Lithia Park, a stunning green space great for leisurely walks and picnics.

Another excellent option is the Ashland Historic District, where you can immerse yourself in the town's rich history. This area boasts well-preserved architecture and a quaint, laid-back vibe. Here, you can visit the iconic Ashland Springs Hotel and enjoy the local dining scene, which features a variety of restaurants suiting different tastes. The proximity to the festival and the park enhances the appeal of this neighbourhood, creating a delightful balance of culture and nature.
How much does it cost to rent a vacation home in Ashland?
Prices for vacation 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 travelling 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.
Are there any discounts for Ashland vacation 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 closest ski area is Mount Ashland, located just a short drive from the town. In Ashland itself, travellers can find a variety of charming vacation rentals, ranging from cosy cabins to modern condos. Many of these accommodations come equipped with essential amenities such as full kitchens, heated living spaces, and outdoor decks or patios, superb for relaxing after a day on the slopes.

In the town of Ashland, visitors can enjoy a vibrant arts scene, renowned for the Oregon Shakespeare Festival, alongside a selection of local restaurants and shops. Some properties may offer additional comforts like fireplaces and hot tubs, enhancing the après-ski experience. For those looking for a more rustic feel, nearby areas such as Talent and Phoenix provide opportunities to stay in quaint farmhouses or lodges, often surrounded by beautiful landscapes and offering easy access to both skiing and hiking trails.
What is the most popular type of vacation rental accomodation in Ashland?
In Ashland, vacation houses are the most popular type of rental accommodation, with approximately 123 available throughout the area. These properties typically offer spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor spaces such as patios or gardens, making them ideal for families or groups. Many are situated near the charming downtown area, providing easy access to local shops, restaurants, and the renowned Oregon Shakespeare Festival.
Are there any family house rentals in Ashland?
In Ashland, Oregon, there are numerous family-friendly rentals available, with around 102 options to choose from. This charming town is renowned for its vibrant arts scene and the famous Oregon Shakespeare Festival, making it an excellent choice for families looking to enjoy cultural experiences together.

Visitors can find spacious homes in neighbourhoods like the Historic District or near Ashland Creek, offering amenities such as fully equipped kitchens for preparing family meals, large living areas for relaxing after a day of exploration, and outdoor spaces where children can play. Many properties also include features like private gardens, game rooms, and even hot tubs, adding to the comfort of your stay.
Can I rent a vacation home with a pool or hot tub in Ashland?
In Ashland, there are several vacation homes available for rent that feature pools and hot tubs, making it a great choice for travellers seeking relaxation. The town is well-known for its vibrant arts scene and proximity to the stunning landscapes of southern Oregon. Many of these properties can be found in scenic neighbourhoods, offering a blend of comfort and natural beauty.
Can I find long-stay vacation rentals in Ashland?
A long-stay vacation 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, travellers can find a variety of pet-friendly house rentals, with over a hundred options available. Many of these properties come equipped with modern amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces like patios or gardens, making them suitable for families or groups enjoying a getaway with their pets.

The neighbourhood surrounding the Oregon Shakespeare Festival is particularly charming, offering a vibrant arts scene and access to local parks where pets can enjoy the outdoors. Lithia Park is a great highlight, featuring extensive walking trails, lush gardens, and pet-friendly areas, providing a wonderful backdrop for leisurely strolls with your furry companions.
Are there any remote work vacation rentals in Ashland?
In Ashland, Oregon, there are numerous remote work vacation rentals available, with around 178 options suiting those looking to blend work and leisure. This vibrant town is renowned for its cultural scene, particularly the Oregon Shakespeare Festival, and offers a variety of outdoor activities with its proximity to beautiful parks and hiking trails.

Travellers can expect properties equipped with essential remote work amenities such as high-speed Wi-Fi, dedicated workspaces including desks and comfortable chairs, and some even feature additional conveniences like computer monitors and safes for secure storage. Many rentals also provide inviting living spaces that encourage relaxation after a productive day, along with amenities like fully equipped kitchens, laundry facilities, and outdoor areas to enjoy the scenic surroundings. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Ashland vacation rentals with parking?
Vrbo offers a wide selection of vacation 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 vacation 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 vacation rental?
The best time to visit Ashland for a vacation rental is during the peak season from June to August, with July being particularly popular among travellers. This vibrant period draws in visitors eager to enjoy the famous Oregon Shakespeare Festival, which showcases world-class theatre in a charming outdoor setting. The warm summer weather, with temperatures averaging around 25 to 30 degrees Celsius, creates a friendly space for outdoor activities, including hiking in the nearby Siskiyou Mountains and exploring the lush local parks.

As the peak season unfolds, Ashland comes alive with a bustling energy, making it a fantastic choice for those who appreciate lively cultural experiences and dynamic social scenes. The beautiful gardens, artisanal shops, and local eateries are great for leisurely strolls after a day of exploration.

For those seeking more budget-friendly options, consider visiting in December. Although this month is typically quieter, it offers a unique charm with festive decorations and a chance to experience Ashland's serene winter beauty. You can still enjoy local attractions without the crowds, making it an ideal time for a peaceful retreat.
How early should I book a Ashland vacation rental?
Book your Ashland vacation 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 vacation 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 immerse themselves in a variety of attractions that highlight the town's unique charm and cultural offerings. The Oregon Shakespeare Festival, located in the downtown area, is a major draw, providing a rich array of theatrical performances throughout the year. The surrounding streets are lined with quaint shops and restaurants, making it an ideal place to enjoy a leisurely stroll.

Lithia Park, situated near the centre of Ashland, is a beautiful green space featuring walking trails, ponds, and picnic areas, great for outdoor enthusiasts and families seeking relaxation. The park's scenic landscapes also host various events and festivals throughout the year, adding to its allure.

For those interested in the arts, the Ashland Art Centre showcases local artists and frequently offers workshops and exhibitions. Additionally, the nearby Southern Oregon University often hosts cultural events and sports activities, providing further entertainment options for visitors.
Can I change or cancel my Ashland home rental booking on Vrbo?
To find Ashland vacation 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 vacation 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.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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