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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.

Ashland Mid-century With Hot Tub/yard! - Ashland, OR
10 2 reviews

Ashland Mid-century With Hot Tub/yard!

apartment, Ashland
This Ashland guest suite, near downtown, offers convenient access to Ashland's shops and restaurants.
The newly decorated 3-bedroom, 2-bathroom upstairs suite includes a porch with views, a shared fenced yard, a hot tub, and accommodates up to 5 guests with pets welcome.
Affordable Luxury- One Block To Downtown - Ashland, OR
9.9 228 reviews

Affordable Luxury- One Block To Downtown

apartment, Ashland
This charming one-bedroom apartment is situated in downtown Ashland, just a short walk from the city's best restaurants. It has received excellent ratings for location, cleanliness, and user experience.
The apartment features a comfortable king-sized bed and a modern bathroom, perfect for couples or solo travelers. You can enjoy the outdoors on your private balcony patio, and the apartment also includes a small refrigerator, microwave, and beverage station for your convenience.
Lodging And Art Gallery, Walk Everywhere. - Ashland, OR
9.9 116 reviews

Lodging And Art Gallery, Walk Everywhere.

apartment, Ashland
This charming house is located in Ashland's Historic Railroad District, just a 10-minute walk from the Oregon Shakespeare Festival and the Ashland Library. It boasts excellent user, location, and cleanliness ratings.
This one-bedroom, one-bathroom home offers 950 square feet of space and accommodates up to 4 guests. The house features a fully equipped kitchen, a private garden, a swimming pool, and a terrace, providing everything you need for a comfortable and enjoyable stay.
Luxuriously Comfortable & Peaceful Getaway Downtown Ashland, With Views. - Ashland, OR
10 57 reviews

Luxuriously Comfortable & Peaceful Getaway Downtown Ashland, With Views.

apartment, Ashland
This Ashland apartment rental, located in the Siskiyou-Hargadine Historic District, is steps from the Oregon Cabaret Theatre, Lithia Park, and the Oregon Shakespeare Festival, with the Thomas and Angus Bowmer Theatres a 5-minute walk away.
This 440-square-foot unit features one bedroom, one bathroom, sleeps two guests, and includes a kitchenette, balcony, fireplace, Smart TV, free WiFi, and on-site parking.

Best Ashland, OR vacation rentals with air conditioning

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.
The Peerless Hotel | Honeymoon Suite #7 | Private Jacuzzi | Mountain Views - Ashland, OR
No reviews

The Peerless Hotel | Honeymoon Suite #7 | Private Jacuzzi | Mountain Views

apartment, Ashland
The Peerless Hotel's Honeymoon Suite #7 is situated in Ashland's Historic Railroad District, near North Mountain Park and the Rogue River-Siskiyou National Forest.
This one-bedroom, one-bathroom suite offers a queen-size bed, a private balcony with mountain views, a jetted jacuzzi tub, and a 20% discount on Oregon Shakespeare Festival tickets.
The Carriage House, Winner 2025 Best Of Ashland! - Ashland, OR
9.8 297 reviews

The Carriage House, Winner 2025 Best Of Ashland!

apartment, Ashland
This apartment is located in Ashland's Historic Downtown District, just a 5-minute walk from the Oregon Shakespeare Festival and close to shops, restaurants, and other attractions. It has consistently received excellent ratings for location, cleanliness, and user experience.
The rental is a one-bedroom, one-bathroom unit that comfortably sleeps four guests. It includes a fully equipped kitchen, air conditioning, a private garden, and access to a swimming pool during the summer months.
Château Herbe ~ Vienna Room - Ashland, OR
9.8 128 reviews

Château Herbe ~ Vienna Room

castle, Ashland
Château Herbe is a modern chateau located in Ashland, Oregon, just minutes from Interstate 5 and downtown Ashland, making it convenient for exploring the Oregon Shakespeare Festival, Lithia Park, and other local attractions.
The one-bedroom, one-bathroom inn features a private patio, a shared sunroom, library, coffee bar, and access to the vineyard, gardens, orchards, pond pergola, and classical fountain.

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.

Swank Suites | Step Free King - Pet Friendly - Ashland, OR
9.0 4 reviews

Swank Suites | Step Free King - Pet Friendly

apartment, Ashland
This Ashland Railroad District apartment rental is one block from a grocery store and coffee shop, two blocks from an escape room, and within walking distance of downtown restaurants, the Plaza Center, and the Chozu Bath & Tea Gardens.
The 400-square-foot unit features a king-size bed, a 90-inch leather sofa, a kitchenette, a private outdoor lounge, and a 65-inch smart TV with Netflix, accommodating two guests and offering convenient access to biking and hiking trails.
The Ashland Social | Entire Estate - Ashland, OR
10 19 reviews

The Ashland Social | Entire Estate

apartment, Ashland
This Ashland vacation home is conveniently located near Southern Oregon University and the Schneider Museum of Art, a short 15-minute walk away, and within one mile of North Mountain Park and the Oregon Cabaret Theatre.
This 3,040-square-foot house boasts five bedrooms, five bathrooms, and accommodates up to twelve guests, featuring a private pool, jacuzzi, sauna, and a fully equipped kitchen with modern appliances.
Swank Suites + Private Porch Patio - Ashland, OR
9.6 7 reviews

Swank Suites + Private Porch Patio

apartment, Ashland
This Premier Suite, located in Ashland's Historic Railroad District, is one block from a grocery store and coffee shop, and within walking distance of downtown restaurants, Ashland Plaza Center, and Chozu Bath & Tea Gardens.
This 400-square-foot first-floor unit features a king-size bed, a kitchenette with microwave and mini-refrigerator, a private balcony, a large jetted tub, high-speed 5G internet, and accommodates two guests.
Anne Hathaway, 8 Bedrooms, 9 Bathrooms, A Commercial Kitchen And Dining Room. - Ashland, OR
10 9 reviews

Anne Hathaway, 8 Bedrooms, 9 Bathrooms, A Commercial Kitchen And Dining Room.

apartment, Ashland
The Anne Hathaway House is located in Ashland's Siskiyou-Hargadine Historic District, just a short walk from North Mountain Park and Lithia Park. This neighborhood offers a peaceful retreat while still being within easy reach of attractions like the ScienceWorks Hands-On Museum and The RRRink.
This 8-bedroom, 9-bathroom rental offers 1610 square feet of space, making it ideal for large groups. The Anne Hathaway House features a commercial kitchen, a formal dining room, multiple living areas, a private outdoor space, in-unit laundry, and a variety of bedroom configurations.

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.

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.
Luxury Ashland Mountain Escape: Pool, Hot Tub - Ashland, OR
9.8 9 reviews

Luxury Ashland Mountain Escape: Pool, Hot Tub

house, Ashland
This Ashland waterfront villa, near Weisinger Family Winery and Southern Oregon University, offers stunning views and proximity to Schneider Museum of Art and Emigrant Lake.
The 3800-square-foot home features four bedrooms, four bathrooms, a private pool and hot tub, and accommodates up to twelve guests, with a fully equipped kitchen and in-house laundry.
Cozy European Cottage 2 Bd + 1 Bath - Ashland, OR
9.3 3 reviews

Cozy European Cottage 2 Bd + 1 Bath

house, Ashland
This Ashland, Oregon house rental is conveniently located near various attractions, though precise distances aren't specified.
The 2-bedroom, 1-bathroom home sleeps 2 guests and boasts a fully equipped kitchen with appliances like a bread maker and air fryer, plus three TVs with Roku, a washer/dryer, and a dedicated workspace with Wi-Fi.
Ashland Group Retreat! The Redtail Inn Offers 3 Full Suites Within One Booking, Sleeping Up To 12. Great Location For The Shakespeare Festival. Ample Space For Your Large Family Or Friend Group. - Ashland, OR
8.8 6 reviews

Ashland Group Retreat! The Redtail Inn Offers 3 Full Suites Within One Booking, Sleeping Up To 12. Great Location For The Shakespeare Festival. Ample Space For Your Large Family Or Friend Group.

apartment, Ashland
This Ashland apartment rental, located in the Siskiyou-Hargadine Historic District, is a short walk from the Oregon Cabaret Theatre, Allen Elizabethan Theatre, and Ashland Library.
This 2,800-square-foot, six-bedroom residence sleeps twelve guests and features a fully equipped kitchen, a jacuzzi, a terrace, a garden, and free Wi-Fi.

Best Ashland, OR vacation rentals with parking

Hanna's House By Wanderlodges - Ashland, OR
9.9 13 reviews

Hanna's House By Wanderlodges

house, Ashland
Cowslip's Quiet, Central, Cuckoo-bud Suite - Ashland, OR
9.7 54 reviews

Cowslip's Quiet, Central, Cuckoo-bud Suite

apartment, Ashland
Private Garden Cottage W Sauna In Rr District - Ashland, OR
9.8 456 reviews

Private Garden Cottage W Sauna In Rr District

house, Ashland
Phoenix Pine Cottage - Ashland, OR
9.3 710 reviews

Phoenix Pine Cottage

apartment, Phoenix

Compare Luxury Vacation Rentals in Ashland, OR

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

The Peerless Hotel | Anniversary Suite #3 | Twin Soaking Tubs | Historic District - Ashland, OR
10 2 reviews

The Peerless Hotel | Anniversary Suite #3 | Twin Soaking Tubs | Historic District

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.

Abbott's Cottages- Heron - Ashland, OR
9.9 106 reviews

Abbott's Cottages- Heron

apartment, Ashland
Come Stay At Our Farmhouse! A Place To Integrate All The Beauty Surrounding You! - Ashland, OR
9.8 38 reviews

Come Stay At Our Farmhouse! A Place To Integrate All The Beauty Surrounding You!

farm, Ashland
House + 2 Studios- 3 Blocks From The Plaza! - Ashland, OR
9.9 42 reviews

House + 2 Studios- 3 Blocks From The Plaza!

house, Ashland
Charming House Two Blocks From Downtown Ashland - Ashland, OR
9.6 12 reviews

Charming House Two Blocks From Downtown Ashland

apartment, 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.

2 Full Beds  Smoking - Ashland, OR
No reviews

2 Full Beds Smoking

apartment, Medford
Medford Home And 2 Condos With Pool - Ashland, OR
No reviews

Medford Home And 2 Condos With Pool

house, Medford
2 Full Beds - Ashland, OR
No reviews

2 Full Beds

apartment, Medford
2 Full Beds  Micfridge - Ashland, OR
No reviews

2 Full Beds Micfridge

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.

Refurbished Barn On Acerage Just Outside Ashland - Ashland, OR
9.8 11 reviews

Refurbished Barn On Acerage Just Outside Ashland

house, Ashland
Chateau Herb ~ Juliet Carriage House Studio - Ashland, OR
8.8 8 reviews

Chateau Herb ~ Juliet Carriage House Studio

studio, Ashland
Modern Mountain Views W/sauna, Cold Plunge&hot Tub - Ashland, OR
10 1 review

Modern Mountain Views W/sauna, Cold Plunge&hot Tub

apartment, Ashland
Historic Ohana House - Walk To Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly - Ashland, OR
9.8 77 reviews

Historic Ohana House - Walk To Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

apartment, Ashland
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