Ashland Rentals
- From $274 per night (USD)
VRBO
Barclay Klum House by WanderLodges | Blocks to OSF
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This 2-bedroom, 1-bath gem, nestled within a mile of Ashland's vibrant downtown, welcomes you to experience this Queen A ...
From $274 per night (USD)VRBO
- From $149 per night (USD)
Expedia
Hyatt Prairie Cabin offers views and a two person Hot Tub! Both bedrooms have a queen size bed.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
About this space Welcome to your Hyatt Prairie Cabin with views and a two person Hot Tub! The primary bedroom, located ...
From $149 per night (USD)Expedia
- From $199 per night (USD)
VRBO
1 bedroom, 1 bathroom cottage with sleeper sofa & full kitchen.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Bluemoon Cottage is a perfect getaway for a couple or friends visiting Ashland, OR. The one bedroom (queen bed), one ...
From $199 per night (USD)VRBO
- From $699 per night (USD)
Expedia
2 units with 6 bedrooms, 6 bathrooms, a kitchen and large dining area.
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 15
About this space The house has five bedrooms, each with its own private bathroom. A gourmet kitchen with a large dining ...
From $699 per night (USD)Expedia
- From $599 per night (USD)
VRBO
Anne Hathaway, 8 bedrooms, 9 bathrooms, a commercial kitchen and dining room.
- Bedrooms:
- 9
- Bathrooms:
- 8
- Sleeps:
- 14
About this space The Anne Hathaway House has seven bedrooms and seven and a half bathrooms, a huge commercial kitchen, ...
From $599 per night (USD)VRBO
- From $749 per night (USD)
Expedia
2 bedrooms, office with sofa bed, sofa bed in living room, 3 bathrooms
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
Ashland's premier luxury destination located in the heart of downtown, the Penthouse encompasses the entire 3rd floor, b ...
From $749 per night (USD)Expedia
- From $149 per night (USD)
VRBO
2 bedroom cabin plus loft, huge deck, lodge-style furnishings.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Premium cabin, huge deck, lodge-style furnishings in an Alpine setting at 5200' elevation, just 18 miles east of downtow ...
From $149 per night (USD)VRBO
- From $349 per night (USD)
Expedia
Luxury condo with 2 bedrooms\/2 bathrooms, sleeper sofa, full kitchen.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Ashland's new luxury vacation destination located in the heart of downtown, just steps to the culinary deligh ...
From $349 per night (USD)Expedia
- From $799 per night (USD)
VRBO
Pioneer Mega 3 vacation homes offering 8 Bedrooms, 5 bathrooms, laundry, TV, and kitchens.
- Bedrooms:
- 5
- Bathrooms:
- 8
- Sleeps:
- 22
What this place offers : 8 Bedrooms, 5 bathrooms, laundry , Washing machine , Entertainment , TV , Heating an ...
From $799 per night (USD)VRBO
- From $375 per night (USD)
Expedia
2-story, 3 bedroom modern home with king and queen beds, living room and kitchen.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
About this space This two-story, modern home has three bedrooms. The primary bedroom has a king-sized bed and the guest ...
From $375 per night (USD)Expedia
- From $579 per night (USD)
VRBO
5 bedroom historic home with brand new furnishings, and is perfect for up to 14 guests.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
About this space This spacious five bedroom historic home has been fully renovated, has brand new furnishings, and is p ...
From $579 per night (USD)VRBO
- From $299 per night (USD)
Expedia
Spacious 2 bedroom historic home with two king beds and kitchenette.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
About this space One block from OSF. Enjoy a relaxing getaway at the Pioneer House. originally built in 1904. Up to six ...
From $299 per night (USD)Expedia
- From $335 per night (USD)
VRBO
3 bedrooms include a king and two queen size beds, 2 bathrooms, and kitchenette.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Historic home - One block from OSF. Easy access to dining, wine tasting, and shopping. Originally built in 1904, this ...
From $335 per night (USD)VRBO
- From $274 per night (USD)
Expedia
Luxury condo with king bedroom, two bathrooms, full kitchen.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Plaza North is a luxury vacation destination located in the heart of downtown Ashland, just steps to the culinary deligh ...
From $274 per night (USD)Expedia
- From $142 per night (USD)
VRBO
Central Serenity: 3BDR City Escape
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your dream rental in the historic district of Ashland, Oregon! This SPACIOUS 3 BDR 1904 Queen Anne Victorian ...
From $142 per night (USD)VRBO
- Click For Pricing
Expedia
Casa Amore Cottage: Walkable and pet friendly!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
This historic cottage in the Ashland Railroad District offers one bedroom, 1.5 bathrooms and will accommodate up to four ...
Click For PricingExpedia
- From $90 per night (USD)
VRBO
Light-filled, upper story flat, walking distance to Oregon Shakespeare Festival
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The open plan of this flat makes it a perfect place to enjoy time with family—or lots of “me” time! The full kitchen mea ...
From $90 per night (USD)VRBO
- From $197 per night (USD)
VRBO
Just a half-mile from Ashland's charming downtown!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
FURNISHED RENTAL No pets preferred. One cat or small dog (under 20 lbs) may be negotiable upon owner approval, excellent ...
From $197 per night (USD)VRBO
- From $105 per night (USD)
VRBO
Private and quiet luxury studio suite on three acres overlooking Ashland.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located on three acres overlooking Ashland, yet just minutes away from everything Ashland has to offer, this private lux ...
From $105 per night (USD)VRBO
- From $399 per night (USD)
Expedia
The Blue Moon House has 5 bedrooms, each with a private bath, plus kitchen, dining and living area.
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 11
Built in the early 1900's and fully renovated. The Blue Moon House has it all! Five bedrooms offering a king or queen b ...
From $399 per night (USD)Expedia
- Click For Pricing
VRBO
Quiet Bellview Retreat Front
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
his is the front half of a large updated older house. It is fully furnished and ready to occupy. Both bedrooms are upsta ...
Click For PricingVRBO
- Click For Pricing
Expedia
Quiet Bellview Retreat Rear
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Located on the south edge of Ashland, and set back from the street, this quiet one-bedroom is fully furnished and privat ...
Click For PricingExpedia
- From $223 per night (USD)
VRBO
Hanna's House | Downtown Oasis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience the charm of this award-winning one-bedroom retreat in downtown Ashland, Oregon, where meticulous craftsmansh ...
From $223 per night (USD)VRBO
- From $149 per night (USD)
Expedia
Charming house two blocks from downtown Ashland
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Serendipity House is a comfortably stylish escape in the heart of Ashland. Our newly remodeled home has all the comf ...
From $149 per night (USD)Expedia
- From $395 per night (USD)
VRBO
The Victorian Secret - Just Steps to Theatres, Plaza, Restaurants & Park. ENJOY!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Click the Video Tab above and take a video virtual tour. Book and enjoy the whole house for yourselves! Perfect locati ...
From $395 per night (USD)VRBO
- From $550 per night (USD)
Expedia
Alley-By Loft
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
This stylish space is centrally located in the heart of downtown Ashland. Enjoy this modern home with a stunning roof-t ...
From $550 per night (USD)Expedia
- Click For Pricing
VRBO
Cozy European Cottage 2 bd + 1 bath
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
About this space Kick back and relax in this calm, stylish space. A rental agreement is listed in detail under house rul ...
Click For PricingVRBO
- From $405 per night (USD)
Expedia
Centrally located Historic Home with parking
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Experience history and enchantment at our Ashland, Oregon home built in 1887. Our home is minutes walk to everything and ...
From $405 per night (USD)Expedia
- Click For Pricing
VRBO
Brand New Crowson Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
About this space The Crowson Cottage is located in a beautiful private setting, close to many amazing wineries and withi ...
Click For PricingVRBO
- From $132 per night (USD)
Expedia
Luxuriously comfortable & peaceful getaway downtown Ashland, with views.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Considering the central location of this little gem, it is amazingly peaceful. There is a long driveway that takes you ...
From $132 per night (USD)Expedia
- From $776 per night (USD)
VRBO
Luxury Ashland Mountain Escape: Pool, Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: Live the Southern Oregon paradise life at the Jefferson Estate — a fabulously appointed home on 8 acres, perfec ...
From $776 per night (USD)VRBO
- From $174 per night (USD)
VRBO
Beautiful little place. Walk to town and theaters!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Nice things come in small packages! While this home is small it is delightfully eloquent. Sparkling clean with a moder ...
From $174 per night (USD)VRBO
- From $109 per night (USD)
VRBO
Mexico Apartment at Wood Hamlet. Lovely gardens. 10 minute walk to town.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Warm and colorful unit filled with Mexican folkart. Stunning gardens with private areas and a pond for swimming. Short w ...
From $109 per night (USD)VRBO
- From $141 per night (USD)
VRBO
Comfortable, Private Guest Lodging
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 3
Excellent value, suite in building separate from the house. Comfortable, spacious, clean with high-quality queen bed, pu ...
From $141 per night (USD)VRBO
- From $469 per night (USD)
VRBO
Modern Custom Home in the Ashland Hills
- Bedrooms:
- 5
- Bathrooms:
- 2
- Sleeps:
- 6
5 minutes from Ashland's plaza. Experience solitude in this wooded sanctuary with views of nature from every room of thi ...
From $469 per night (USD)VRBO
- From $179 per night (USD)
Expedia
The Oberon Suite - One Bedroom Apartment in a Castle with Sweeping Views\n\n
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This chateau apartment is nothing short of magical. Enjoy a tranquil environment with breathtaking views of the estate g ...
From $179 per night (USD)Expedia
- From $135 per night (USD)
VRBO
Ashland Mid-Century with a Yard!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
3 bedroom, 2 bath with dedicated office space, hardwood floors, private porch with a beautiful view, utilities included, ...
From $135 per night (USD)VRBO
- From $595 per night (USD)
Expedia
Historic Dunn Ranch Ashland Oregon. Sleeps 12 to 14 Great for large groups.\n
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
Driving through the front gates you will find this Gorgeous and Stunning, completely refurbished, updated farmhouse orig ...
From $595 per night (USD)Expedia
- From $179 per night (USD)
VRBO
Romantic Getaway in Gated Castle Community - The Rosalind
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
About the Space: This comfortable carriage house apartment is nestled in a gated castle community that boasts classical ...
From $179 per night (USD)VRBO
- From $125 per night (USD)
Expedia
Edward Gorey Cottage, walk to town
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Edward Gorey Cottage sleeps up to 2 adults and is perfect for those who wish to enjoy artful living close to downtown As ...
From $125 per night (USD)Expedia
- From $178 per night (USD)
VRBO
Monthly Rental Circular House blocks to Downtown & Oregon Shakespeare Festival
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
A unique circular single-family house just blocks from Ashland's downtown dining & entertainment, Lithia Park, and the r ...
From $178 per night (USD)VRBO