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Ashland, OR vacation rentals
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Best Vacation rentals and Airbnb offers in Ashland, OR

Search Vacation Rentals near the Old Town in Ashland, OR

Choose a downtown Ashland, OR vacation rental for easy sightseeing. Compare the top centrally located properties and book your city stay with confidence.

Abbott's Cottages - Falcon - Ashland, OR
9.9 176 reviews

Abbott's Cottages - Falcon

apartment, Ashland
This charming cottage is located in a quiet neighborhood in Ashland, just a short walk from the downtown area and a few blocks from the Oregon Shakespeare Festival. It boasts excellent user, location, and cleanliness ratings, making it a great option for travelers visiting Ashland. This 2-bedroom, 2-bathroom home comfortably sleeps 6 guests. The cottage features a fully equipped kitchen with a fridge, microwave, and dishwasher, as well as air conditioning, a garden, and parking.
Sweet Breeze Bungalow - Ashland, OR
10 141 reviews

Sweet Breeze Bungalow

apartment, Ashland
This Ashland, Oregon bungalow, located in the Railroad District, is a five-minute walk from downtown and walking distance to the Shakespeare Festival theaters, Lithia Park, and the Japanese Garden.
The recently remodeled one-bedroom, one-bathroom cottage sleeps three guests and features a full kitchen with dishwasher, air conditioning, private parking, and a garden.
Modern Airy Retreat - Views, Walk To Everything - Ashland, OR
9.9 214 reviews

Modern Airy Retreat - Views, Walk To Everything

house, Ashland
This Ashland Railroad District studio apartment is a five-minute walk from downtown, ten minutes from Lithia Park and the Oregon Shakespeare Festival.
The modern unit, sleeping two, features a well-equipped kitchenette with coffee supplies and dedicated off-street parking—a rare find in downtown Ashland—and offers proximity to Noble Coffee Roasters, Peerless Restaurant, and the Bear Creek Bike Trail.
The Mountain House By Wanderlodges - Ashland, OR
9.4 37 reviews

The Mountain House By Wanderlodges

house, Ashland
The Mountain House by WanderLodges is located in Ashland, just a short walk from the ScienceWorks Museum, the Oregon Shakespeare Festival, and the Schneider Museum of Art. This vacation rental has received excellent ratings for location, cleanliness, and overall user experience.
The house has 3 bedrooms and 2 bathrooms, offering space for up to 6 guests. The fully equipped kitchen, air conditioning, free Wi-Fi, and private parking make this a comfortable and convenient place to stay.

Best Ashland, OR vacation rentals with air conditioning

Mt Ashland Homestead, Ashland 10 M., Right By Pct - Ashland, OR
9.9 599 reviews

Mt Ashland Homestead, Ashland 10 M., Right By Pct

apartment, Ashland
This vacation home is located in the mountains of Ashland, just a short walk from the Cascade-Siskiyou National Monument and a short drive from Emigrant Lake and the Tashi Choling Buddhist Center. This property has received excellent ratings for its location, cleanliness, and overall experience.
The house is spacious, with 4,700 square feet of living space. It offers a range of amenities, including a swimming pool, jacuzzi, sauna, and a fully equipped kitchen, making it perfect for families and groups looking for a relaxing and enjoyable stay.
Cozy European Cottage 2 Bd + 1 Bath - Ashland, OR
10 2 reviews

Cozy European Cottage 2 Bd + 1 Bath

cabin, Ashland
This Ashland, Oregon cabin rental is conveniently located within a 10-minute walk of Southern Oregon University, the Schneider Museum of Art, and ScienceWorks Hands-On Museum, and less than a mile from North Mountain Park and the Ashland Library.
This 800-square-foot lodge features two bedrooms, one bathroom, and accommodates two guests, offering a fully equipped kitchen, fireplace, private terrace, access to a fitness center, spa, and free Wi-Fi.
Cowslip Historic Main House, Great For Gatherings! - Ashland, OR
10 24 reviews

Cowslip Historic Main House, Great For Gatherings!

house, Ashland
This charming apartment is just two blocks from Ashland's downtown, putting you within walking distance of restaurants, shops, and the Oregon Shakespeare Festival theater. It's also close to Lithia Park, a beautiful urban oasis with walking trails, gardens, and a picturesque creek. This apartment has excellent ratings for location, cleanliness, and user experience.
The four-bedroom, two-bathroom apartment comfortably sleeps up to eight guests. Enjoy a full kitchen, dining room, air conditioning, parking, and internet access.
Alley-by Loft: Smack Dab In The Middle Of Ashland!  Steps From Theaters & Lithia - Ashland, OR
9.6 5 reviews

Alley-by Loft: Smack Dab In The Middle Of Ashland! Steps From Theaters & Lithia

apartment, Ashland
This condo is located in Ashland's Historic Downtown District, a prime spot steps from restaurants and 0.5 miles from ScienceWorks Hands-On Museum, with easy access to North Mountain Park and the Cascade-Siskiyou National Monument.
This 1730 sq ft apartment offers 3 bedrooms, 2 bathrooms, accommodates 10 guests, and features a full kitchen with a fridge, microwave, and dishwasher, plus a rooftop patio with 360-degree town views.

Frequently Asked Questions about vacation rentals in Ashland, OR

  • What are some interesting places to visit in or near Ashland, OR?

    Ashland is full of interesting places! You can't miss the Oregon Shakespeare Festival, of course. The Lithia Park is beautiful and offers great views of the city. If you're looking for something a little different, head to the Ashland Art Center or the Southern Oregon Historical Society Museum. And don't forget about the nearby Crater Lake National Park, about a 2-hour drive from Ashland.
  • What are the best Airbnb and vacation rentals in Ashland, OR?

  • Which walking or cycling routes are the best in Ashland, OR?

    The Bear Creek Greenway is a popular choice for both walking and cycling. It runs along Bear Creek and offers beautiful views of the surrounding mountains. For a more challenging ride, try the Emigrant Lake Loop, which takes you around Emigrant Lake and through the nearby forest. And if you're looking for a shorter walk, the Lithia Park loop is a great option.
  • What are the most popular Airbnbs in Ashland, OR?

  • What sports or outdoor activites can visitors enjoy in and around Ashland, OR?

    Ashland is a great place for outdoor activities. You can hike, bike, and fish in the surrounding forests and mountains. There's also great skiing and snowboarding at Mount Ashland in the winter. If you're looking for something more relaxed, you can go kayaking or paddleboarding on the Rogue River.
  • What are the best vacation rentals with a pool in Ashland, OR?

  • What other towns or cities can be easily accessed from Ashland, OR?

    You can easily reach Medford, about a 20-minute drive from Ashland. It's a larger city with more shopping and dining options. You can also visit Jacksonville, a historic gold-mining town about 15 minutes away. For a longer trip, you can head to Crater Lake National Park, about a 2-hour drive from Ashland.
  • What are the best rentals for families and kids in Ashland, OR?

  • What amenities are commonly available in vacation rentals in Ashland, OR?

    Most vacation rentals in Ashland will have basic amenities like a kitchen, bathroom, and bedrooms. Many also offer things like Wi-Fi, laundry facilities, and outdoor spaces. Some even have hot tubs or fireplaces. You can usually find rentals with specific amenities by searching online or contacting a local rental agency.
  • What are the best rentals or Airbnbs with a jacuzzi in Ashland, OR?

  • What time of year is best to rent a vacation rental Ashland, OR?

    The best time to visit Ashland depends on what you're looking for. The summer is the most popular time to visit, with warm weather and plenty of outdoor activities. If you're interested in the Oregon Shakespeare Festival, the summer is the time to go. Fall is also beautiful, with colorful leaves and cooler temperatures. Spring is a good time to visit if you want to avoid the crowds and enjoy the wildflowers.

Popular destinations

Best Vacation Rentals with Balconies in Ashland, OR

Enjoy your own private terrace with city skyline views at these vacation rentals in Ashland, OR.

The Ashland Social | Main House - Ashland, OR
10 36 reviews

The Ashland Social | Main House

apartment, Ashland
This Ashland apartment is located just a short drive from the Oregon Shakespeare Festival and the Ashland Plaza, making it a convenient base for exploring the city's cultural attractions and vibrant downtown. The apartment has received excellent user ratings, indicating a high level of satisfaction from previous guests.
This spacious 3,040 square foot home can comfortably accommodate up to 10 guests with its three bedrooms and four bathrooms. The apartment features a fully equipped kitchen, multiple dining areas, a private outdoor oasis with a hot tub, a well-equipped gym, and a sauna, offering everything you need for a relaxing and enjoyable stay.
Historic Farm Estate | Fairytale Haven | Ashland - Ashland, OR
8.6 10 reviews

Historic Farm Estate | Fairytale Haven | Ashland

apartment, Phoenix
This Phoenix, Oregon farmhouse rental sits between Jacksonville's wine country and Ashland's Shakespeare Festival, offering easy access to both.
The six-bedroom property includes a mother-in-law suite and a cottage, accommodating up to 17 guests and boasting a kitchen with a fridge and microwave, air conditioning, a terrace, and a garden; nearby attractions include the Craterian Ginger Rogers Theatre and Beekman House.
Lithia Springs Resort - Ashland, OR
No reviews

Lithia Springs Resort

resort, Ashland
Lithia Springs Resort in Ashland, Oregon is located 2.5 miles from the city center, offering convenient access to Ashland's attractions.
This hotel boasts amenities including indoor and outdoor swimming pools, a spa, fitness center, business center, and on-site dining, ensuring a comfortable and convenient stay.
Cabin In The Mountains Of Ashland - Ashland, OR
9.2 7 reviews

Cabin In The Mountains Of Ashland

apartment, Ashland
This Oregon cabin rental, located 15 minutes from Ashland, Oregon, near the California border, offers easy access to both the city's amenities and the natural beauty of the Cascade-Siskiyou National Monument and North Mountain Park.
This four-bedroom, three-bathroom lodge sleeps eight guests and features a private sauna, a well-stocked coffee bar, spacious upstairs and downstairs entertaining areas, a terrace, and a yard; pet-friendly with internet and parking.

Neighborhoods and points of interest in Ashland, OR

Top Vacation Rentals for Families in Ashland, OR

Booking a family-oriented vacation rental in Ashland, OR keeps you close to top city attractions for a stress-free getaway.

Street Level Flat In Great Downtown Location "A" - Ashland, OR
9.7 223 reviews

Street Level Flat In Great Downtown Location "A"

apartment, Ashland
This house is in Ashland's Historic Railroad District, just a 10-minute walk from the Ashland Library, Oregon Cabaret Theatre, and Allen Elizabethan Theatre. The property has excellent ratings for location, cleanliness, and user experience.
This 3-bedroom, 2-bathroom home has a fully equipped kitchen, a patio, and a washing machine. Enjoy a smoke-free environment, parking, and internet access during your stay.
Charming Medford Getaway ~ 4 Miles To Downtown! - Ashland, OR
No reviews

Charming Medford Getaway ~ 4 Miles To Downtown!

house, Medford
Vacation rental. Your accommodation will be located in Medford.
Facilities and services include free parking, a kitchen and an iron. Take advantage of the air conditioning in this house in Medford.
Charming House Two Blocks From Downtown Ashland - Ashland, OR
9.6 12 reviews

Charming House Two Blocks From Downtown Ashland

apartment, Ashland
The Serendipity House is centrally located in Ashland, Oregon, two blocks from restaurants, shops, and theaters, offering easy access to the Oregon Cabaret Theatre and Allen Elizabethan Theatre.
This two-bedroom, one-bathroom home sleeps four guests and features a fully equipped kitchen with a complimentary coffee bar, air conditioning, a private garden, parking, and high-speed internet access.
Manor Hill Haven Hot Tub & Accessible Features - Ashland, OR
10 1 review

Manor Hill Haven Hot Tub & Accessible Features

house, Medford
Manor Hill Haven, a 2-bedroom vacation home, is located 5 miles from Rogue Valley International-Medford Airport and 11 miles from the Oregon Shakespeare Festival, Lithia Park, and the Oregon Cabaret Theatre.
This 1600 square foot residence accommodates up to 9 guests with air conditioning, a Jacuzzi, a balcony, a garden, and a kitchen equipped with a fridge, microwave, and dishwasher, offering free Wi-Fi and private parking.

Best Ashland, OR vacation rentals with parking

Whimsy On B | The Studio - Ashland, OR
10 10 reviews

Whimsy On B | The Studio

apartment, Ashland
Mountain Ave House By Wanderlodges - Ashland, OR
10 11 reviews

Mountain Ave House By Wanderlodges

apartment, Ashland
Chateau Herbe ~ Rosalind Carriage House Beautiful 1 Bedroom Apartment - Ashland, OR
9.2 7 reviews

Chateau Herbe ~ Rosalind Carriage House Beautiful 1 Bedroom Apartment

apartment, Ashland
Escape To Manor Hill Haven! Accessible 2br Retreat With Hot Tub, Modern Comfort & Mountain Views. Perfect For Families, Couples & Business Travelers. - Ashland, OR
9.6 9 reviews

Escape To Manor Hill Haven! Accessible 2br Retreat With Hot Tub, Modern Comfort & Mountain Views. Perfect For Families, Couples & Business Travelers.

apartment, Medford

Compare Luxury Vacation Rentals in Ashland, OR

Discover ultimate relaxation in a luxury Ashland, OR vacation rental, where comfort meets a central, prime location.

Chateau Herbe ~ Rosalind Carriage House 1bdr Apt - Ashland, OR
9.8 17 reviews

Chateau Herbe ~ Rosalind Carriage House 1bdr Apt

apartment, Ashland

Our Favorite Pet-Friendly Vacation Rentals in Ashland, OR

Discover dog-friendly vacation rentals in Ashland, OR situated perfectly for city walks and nearby dog parks.

Paschal Winery - Dream 1 Cottage - Ashland, OR
9.0 2 reviews

Paschal Winery - Dream 1 Cottage

apartment, Talent
Charming Medford Getaway ~ 4 Miles To Downtown! - Ashland, OR
9.3 55 reviews

Charming Medford Getaway ~ 4 Miles To Downtown!

house, Medford
Cozy European Cottage 2 Bd + 1 Bath - Ashland, OR
9.3 3 reviews

Cozy European Cottage 2 Bd + 1 Bath

house, Ashland
Charming Carriage House In Ashland Near Downtown - Ashland, OR
10 13 reviews

Charming Carriage House In Ashland Near Downtown

cottage, Ashland

Explore Vacation Rentals with a Pool in Ashland, OR

Choose an Ashland, OR rental with a pool for a refreshing swim right in the heart of the city.

Lithia Springs Resort - Ashland, OR
9.2 1619 reviews

Lithia Springs Resort

resort, Ashland
The Ashland Social | Entire Estate - Ashland, OR
10 19 reviews

The Ashland Social | Entire Estate

apartment, Ashland
Capital House- Private Getaway With Pool! - Ashland, OR
10 40 reviews

Capital House- Private Getaway With Pool!

apartment, Medford

Search Vacation Rentals with Jacuzzi in Ashland, OR

Unwind after a day of urban exploration with a private hot tub at your own vacation rental in Ashland, OR.

Come Relax, Work & Enjoy Country Air. - Ashland, OR
9.2 70 reviews

Come Relax, Work & Enjoy Country Air.

apartment, Ashland
Manor Hill Haven | Hot Tub & Accessible Features - Ashland, OR
9.9 118 reviews

Manor Hill Haven | Hot Tub & Accessible Features

apartment, Medford
Historic Dunn Ranch Ashland Oregon. Sleeps 12 To 14 Great For Large Groups. - Ashland, OR
9.8 20 reviews

Historic Dunn Ranch Ashland Oregon. Sleeps 12 To 14 Great For Large Groups.

apartment, Ashland
Modern Design In Ashland For Families W Hot Tub - Ashland, OR
10 6 reviews

Modern Design In Ashland For Families W Hot Tub

apartment, Ashland
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