Vacation Rentals in Ashland, OR

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Ashland, OR holiday rentals
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315 Holiday rentals and Airbnb in Ashland, OR

Elite Family Holiday Rentals in Ashland, OR

Keep the whole group together under one roof with plenty of space to lounge at family holiday rentals in Ashland, OR.

Lithia Springs Resort - Ashland, OR
9.2 1619 reviews

Lithia Springs Resort

resort, Ashland
Lithia Springs Resort is located just 2.5 miles from downtown Ashland and the Oregon Shakespeare Festival, offering easy access to the area's cultural attractions. The resort consistently receives excellent ratings for its location, cleanliness, and overall experience.
The resort features a range of accommodation options, including suites and bungalows, all decorated in a modern spa-themed style. Guests can enjoy a variety of amenities, including mineral spring water soaking bathtubs, a seasonal outdoor saltwater pool, a hot tub, and a complimentary full breakfast.

Best Ashland, OR holiday rentals with parking

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

Chateau Herb ~ Juliet Carriage House Studio

studio, Ashland
This Ashland mountain property is situated approximately 1.6km from Ashland Dog Park and within 4.8km of North Mountain Park and Lithia Park, offering easy access to Ashland's attractions.
The one-bedroom, one-bathroom dwelling sleeps four guests and features a private patio, on-site laundry facilities, and is ideal for short or long stays exploring Ashland's natural beauty and cultural offerings such as the Allen Elizabethan Theatre and Angus Bowmer Theatre.
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 apartment is located in Ashland's Historic Downtown District, offering convenient access to restaurants, ScienceWorks Hands-On Museum, and within 6 kilometers of North Mountain Park and Cascade-Siskiyou National Monument.
This modern condo spans 161 square meters, accommodates up to 10 guests with 3 bedrooms and 2 bathrooms, and features a fully equipped kitchen, air conditioning, a garden, parking, and a rooftop patio with panoramic views.
Whimsy On B | The Studio - Ashland, OR
No reviews

Whimsy On B | The Studio

studio, Ashland
This studio apartment is situated in central Ashland, a short walk from the Oregon Shakespeare Festival and the Allen Elizabethan Theatre, and within 2 kilometres of Grizzly Peak Winery and Weisinger Family Winery.
The accommodation sleeps two guests and offers a king-size bed, a kitchenette with a toaster oven and hot plate, a private bathroom with a shower, air conditioning, Wi-Fi, and access to a garden and spa, with parking available.
Sunset Cottage At Grizzly Peak Winery - Ashland, OR
9.5 11 reviews

Sunset Cottage At Grizzly Peak Winery

house, Ashland
Sunset Cottage, a studio apartment at Grizzly Peak Winery near Ashland, Oregon, offers vineyard views and easy access to Ashland's attractions.
This self-catering unit sleeps four, features a full kitchen, wood-burning fireplace, smart TV, and complimentary access to winery concerts and food truck meals during the concert season.

Frequently asked questions about holiday rentals in Ashland, OR

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Top-Rated Holiday Rentals with a Balcony in Ashland, OR

Find holiday rentals with a balcony in Ashland, OR and take in the local scenery.

Premier Downstairs Flat In Perfect Down Town Location - Ashland, OR
9.7 223 reviews

Premier Downstairs Flat In Perfect Down Town Location

apartment, Ashland
This three-bedroom house is located in Ashland's Historic Railroad District, just a kilometre from the Ashland Library, Oregon Cabaret Theatre, and Allen Elizabethan Theatre. The property has received excellent ratings for its location, cleanliness, and overall experience.
The house has two bathrooms and a washing machine, providing plenty of space for families or groups. It also features a fully equipped kitchen, a patio, and parking, allowing you to prepare meals, enjoy the outdoors, and relax after a day exploring Ashland's attractions.
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 the Siskiyou-Hargadine Historic District of Ashland, just a short walk from North Mountain Park and Lithia Park. The house is within easy reach of the town's main attractions, making it ideal for exploring everything Ashland has to offer.
This spacious property offers eight bedrooms and nine bathrooms across 150 square metres, making it suitable for large groups or families. The house boasts a commercial kitchen, a formal dining room, a living room with a library, a separate sitting room, a front porch, a garden, a washing machine and a dryer.
Whimsy On B- 1 Block To Downtown Ashland - Ashland, OR
No reviews

Whimsy On B- 1 Block To Downtown Ashland

house, Ashland
This holiday cottage in Ashland offers a prime location, a mere 5-minute stroll from the Oregon Shakespeare Festival and 400 metres from the Oregon Cabaret Theatre, placing it conveniently 1 block from downtown Ashland.
Guests can enjoy air-conditioned rooms with complimentary private parking and WiFi, featuring a terrace, private bathroom, and flat-screen TV, with no bachelor(ette) or similar parties permitted.
Lithia Springs Resort - Ashland, OR
9.2 1619 reviews

Lithia Springs Resort

resort, Ashland
Lithia Springs Resort is located just 2.5 miles from downtown Ashland and the Oregon Shakespeare Festival, offering easy access to the area's cultural attractions. The resort consistently receives excellent ratings for its location, cleanliness, and overall experience.
The resort features a range of accommodation options, including suites and bungalows, all decorated in a modern spa-themed style. Guests can enjoy a variety of amenities, including mineral spring water soaking bathtubs, a seasonal outdoor saltwater pool, a hot tub, and a complimentary full breakfast.

Top-Ranked Pet-Friendly Holiday Rentals in Ashland, OR

Let your dog stretch their legs and explore a new neighborhood alongside you at pet-friendly holiday rentals in Ashland, OR.

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

Abbott's Cottages - Falcon

apartment, Ashland
This charming cottage is situated in a peaceful neighbourhood, just a short walk from the lively centre of Ashland, with its array of shops, restaurants, and theatres. The property has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience.
The cottage is spacious and comfortably accommodates up to six guests. Amenities include a well-equipped kitchen with a fridge, microwave oven, and dishwasher, as well as air conditioning, a garden, and parking.
Beautiful Bungalow Downtown Ashland Railroad District, Rv Parking, Adventure! - Ashland, OR
9.0 9 reviews

Beautiful Bungalow Downtown Ashland Railroad District, Rv Parking, Adventure!

apartment, Ashland
This rebuilt vintage bungalow is located a mere 500 metres from Ashland's central plaza and its renowned restaurants, offering easy access to the town's culinary scene.
This 2-bedroom cottage accommodates up to four guests and features two queen beds, a bathroom with an antique clawfoot tub, air conditioning, and is a convenient base for exploring nearby attractions such as North Mountain Park and the Allen Elizabethan Theatre.
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