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Ashland Rentals
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- 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 $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 $103 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 $103 per night (USD)VRBO
- From $77 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 $77 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 $208 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 $208 per night (USD)VRBO
- From $239 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 $239 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 $393 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 $393 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 $101 per night (USD)
VRBO
Nancy's Garden Cottage -1. 5 Blocks to Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
We are located in the heart of Ashland. Only 1 block from Downtown. Enjoy the open Garden and Great location to all Rest ...
From $101 per night (USD)VRBO
- From $205 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 $205 per night (USD)VRBO
- 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
- From $90 per night (USD)
VRBO
Light-filled, upper story flat, walking distance to Oregon Shakespeare Festival
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
(Note: yes, the entire flat is yours. Separate, private entrance from the downstairs flat. No adjoining doors.) The open ...
From $90 per night (USD)VRBO
- From $120 per night (USD)
VRBO
Ashland Boho-Chic with a Yard
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Boho Chic in Ashland! Enjoy a newly renovated boho/modern downstairs apartment with private porch, walking distance to ...
From $120 per night (USD)VRBO
- From $253 per night (USD)
VRBO
Stay & Play: Pool, Hot Tub, Gym and Sauna
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
Luxury 3BR escape with pool, sauna, and gym awaits near the Oregon Shakespeare Festival. Indulge in refined living with ...
From $253 per night (USD)VRBO
- From $415 per night (USD)
VRBO
Second Spring Property - 3 bedroom 2 bath luxury home in the heart of Ashland
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This luxury vacation rental is uniquely designed for elegance and comfort that will make you feel right at home. The new ...
From $415 per night (USD)VRBO
- Click For Pricing
VRBO
Downtown Ashland Earth spa unit with private patio
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 3
The John and Charlotte Pelton House was built in 1894 by Ashland builder W. J. Schmidt. By its size and distinction as a ...
Click For PricingVRBO
- Click For Pricing
VRBO
Ashland Townhouse, furnished
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
3 bedroom, 2 and 1/2 bath furnished townhouse located 1/2 mile from grocery shopping and the YMCA, 1 mile from Southern ...
Click For PricingVRBO
- From $200 per night (USD)
VRBO
Ashland's Mountain View Vacation Rental.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Mountain View Cottage Ashland’s newest vacation rental The perfect place to stay for your next Ashland get a ...
From $200 per night (USD)VRBO
- Click For Pricing
Expedia
Cheerful location on golf course Ashalnd
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Forget your worries in this spacious and serene space. Offering 1 room in downstairs unit in our 5 bedroom house. The ho ...
Click For PricingExpedia
- From $200 per night (USD)
VRBO
Custom Ashland Home with Fantastic Mountain Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautiful 1360 square foot home on 2 acres. Modern, shed roof design with great windows and view of Grizzly Peak. Quiet ...
From $200 per night (USD)VRBO
- From $120 per night (USD)
Expedia
Beautiful Guest Suite with Private Deck Overlooking Forest and Waterfall
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This newly remodeled, modern guest suite is nestled in the Tolman Creek canyon and surrounded by a beautiful madrone, pi ...
From $120 per night (USD)Expedia
- From $150 per night (USD)
VRBO
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Farm Cottage is a renovated former horse hotel. It retains the charm of its former use yet is well appointed and upd ...
From $150 per night (USD)VRBO
- From $167 per night (USD)
Expedia
Romantic Charm on Chateau Grounds - The Juliet
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to the Carriage House Juliet at Chateau Herbe! A state-of-the art contemporary castle estate with stunning groun ...
From $167 per night (USD)Expedia
- From $161 per night (USD)
VRBO
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 $161 per night (USD)VRBO
- From $186 per night (USD)
Expedia
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 $186 per night (USD)Expedia
- From $183 per night (USD)
VRBO
Garden View Apartment in Gated Castle Community
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to the Carriage House Miranda at Chateau Herbe! A state-of-the art contemporary castle estate with stunning grou ...
From $183 per night (USD)VRBO
- From $459 per night (USD)
Expedia
Make memories at The Hux- Ashland
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Features for Unforgettable Family Memories: --4 bedrooms; 3 king, 1 queen, 2 twin --Game Room foosball, darts + ...
From $459 per night (USD)Expedia
- From $161 per night (USD)
VRBO
Serene Family, Cottage-minutes to Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Summary: --> 4 miles to OSF Theatre --> 1/2 mile to Golf Course -->Pet Friendly (fully fenced) Crow's Cottage is a cozy, ...
From $161 per night (USD)VRBO
- From $333 per night (USD)
VRBO
The Best In Ashland: Magnificent View, Privacy, Quality, Convenience, Very Clean
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
3 bedroom, 2 bath villa on acreage within minutes of theaters, restaurants and shopping. Very private with modern kitche ...
From $333 per night (USD)VRBO
- From $450 per night (USD)
VRBO
Asian Inspired Escape with View - Just 3 Miles from Downtown
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Asian meets Craftsman in this two story hillside home perched high above the city lights. Full kitchen with every ameni ...
From $450 per night (USD)VRBO
- From $85 per night (USD)
Expedia
Country's Edge Rooms in just outside of Ashland, convenient for travel
- Bedrooms:
- 0
- Bathrooms:
- 1
- Sleeps:
- 2
Just beyond the southern edge of Ashland, in the country with amazing mountain views, a hop onto I-5, or up the mountai ...
From $85 per night (USD)Expedia
- From $171 per night (USD)
VRBO
Peaceful, spacious home on 8 acres. Pet-friendly, close town, and a creek!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
You will be an easy 10 minute drive from Downtown Ashland and feel like you are out in the country. The home is 1200 squ ...
From $171 per night (USD)VRBO
- From $799 per night (USD)
Expedia
Come stay at our farmhouse! A place to integrate all the beauty surrounding you!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Our family ranch home is nestled at the base of Grizzly Peak, with expansive views of Mt Ashland, and the Rogue Valley. ...
From $799 per night (USD)Expedia
- From $696 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 $696 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 $138 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 $138 per night (USD)VRBO
- From $474 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 $474 per night (USD)VRBO
- From $662 per night (USD)
VRBO
Modern Farmhouse on Emigrant Creek
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy peace indoors and out in this spacious, stunning and serene home. It was built by a renowned local contractor in 2 ...
From $662 per night (USD)VRBO