Bed and Breakfast in Ashland, OR

44 available b&b offers

7 nights
2
1
  • airbnb
  • booking
  • hotelscom
  • vrbo
  • tripadvisor
  • expedia
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Ashland, OR bed and breakfast
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

44 Bed and Breakfasts in Ashland, OR

Best Ashland, OR bed and breakfasts with breakfast included

Country Willows Inn And Estate - Ashland, OR
9.8 37 reviews
Ashland, OR
15/10 – 19/10
SG$390/nighttotal: SG$1560 (4 )

Country Willows Inn And Estate

1 1
B&B , Ashland
Country Willows Inn is conveniently located in Ashland, Oregon, under 3.2 kilometres from Southern Oregon University and the Schneider Museum of Art, with easy access to Lithia Park (approximately 6 kilometres away) and various theatres within a 4.8 kilometre radius.
This nine-room inn offers free full breakfast, an outdoor pool, a relaxing garden terrace, complimentary Wi-Fi, daily housekeeping, complimentary toiletries, and on-site free self-parking; concierge services and gift shops/newsstands are also available.

Best Ashland, OR bed and breakfasts with a garden

The Matriarch Suites- Downtown Ashland, Or - Ashland, OR
9.3 70 reviews
Ashland, OR
15/10 – 19/10
SG$350/nighttotal: SG$1400 (4 )

The Matriarch Suites- Downtown Ashland, Or

1 1
B&B , Ashland
The Matriarch B&B is situated in downtown Ashland, just a short walk from the Oregon Shakespeare Festival and Oregon Cabaret Theatre. It has received excellent ratings for its location, cleanliness, and overall experience.
The guest house has one bedroom and one bathroom, accommodating up to two guests. Amenities include air conditioning, a terrace, a garden, a spa, parking, and free Wi-Fi.
Arden Forest Inn - Ashland, OR
9.3 343 reviews
Ashland, OR
15/10 – 19/10
SG$228/nighttotal: SG$912 (4 )

Arden Forest Inn

1 1
B&B , Ashland
Arden Forest Inn is situated in Ashland, close to Southern Oregon University and around 8 miles from Mt. Ashland Ski Area. This guesthouse consistently receives excellent ratings for its location, cleanliness, and overall experience.
The inn features a range of amenities for a comfortable stay, including a swimming pool, a terrace, and a garden. Guests can also enjoy a restaurant, a bar, and a fitness centre, along with room service and free parking.
Ashland 1 Br King Suite W/gym & Pool - Ashland, OR
Ashland, OR
19/07 – 14/08
SG$417/nighttotal: SG$10842 (26 )

Ashland 1 Br King Suite W/gym & Pool

1 1
B&B , Ashland
This guest house is located near the Rogue Valley, a short drive from Ashland town centre, placing it conveniently close to the Oregon Shakespeare Festival and Southern Oregon University.
This private one-bedroom suite accommodates two guests and features a king-sized bed, a kitchenette with a full-size fridge and microwave, air conditioning, Wi-Fi, a swimming pool, hot tub, and a 24-hour fitness centre, with pets welcome for an additional fee.
Wood Hamlet - Miro Room, Walk To Town - Ashland, OR
9.9 220 reviews
Ashland, OR
15/10 – 19/10
SG$175/nighttotal: SG$700 (4 )

Wood Hamlet - Miro Room, Walk To Town

1 1
B&B , Ashland
This studio apartment is situated in a residential area just a short walk from Ashland's centre, with easy access to restaurants, shops, and the 29-hectare Lithia Park.
The studio features a private entrance, a bathroom with a traditional bathtub and shower, and a peaceful garden with a pond, ideal for relaxing after exploring the local attractions.

Frequently asked questions about bed and breakfast in Ashland, OR

Destinations nearby

Best Ashland, OR bed and breakfasts with parking

Abigail's Bed And Breakfast Inn - Ashland, OR
9.7 158 reviews
Ashland, OR
15/10 – 19/10
SG$373/nighttotal: SG$1492 (4 )

Abigail's Bed And Breakfast Inn

1 1
B&B , Ashland
Abigail's Bed and Breakfast Inn is situated in Ashland, a short walk from the Oregon Shakespeare Festival and a mile from the Oregon Cabaret Theatre. The inn has been rated excellent for its location, cleanliness, and overall user experience.
The accommodation offers air-conditioned rooms, some with fully equipped kitchens and private bathrooms. Guests can enjoy a garden, a picnic area, a swimming pool, and a terrace, along with a restaurant, a concierge service, and free parking.
Sunset Cottage At Grizzly Peak Winery - Ashland, OR
Ashland, OR
08/08 – 10/08
SG$366/nighttotal: SG$732 (2 )

Sunset Cottage At Grizzly Peak Winery

1 4
B&B , Ashland
Sunset Cottage at Grizzly Peak Winery offers a unique vineyard setting in Ashland, located approximately 5.1 to 5.6 kilometres from the Oregon Shakespeare Festival, Oregon Cabaret Theatre, Lithia Park, and Ashland Library.
This one-bedroom guesthouse accommodates up to seven guests, featuring a private terrace, an outdoor dining area, a fully equipped kitchen, air conditioning, a balcony, complimentary private parking, and free WiFi.

Best Ashland, OR bed and breakfasts with air conditioning

Summer’s Night Cottage 8 Minute Walk To Downtown - Ashland, OR
9.8 146 reviews
Ashland, OR
15/10 – 19/10
SG$215/nighttotal: SG$860 (4 )

Summer’s Night Cottage 8 Minute Walk To Downtown

1 1
B&B , Ashland
This Ashland cottage is conveniently located near the centre of Ashland, Oregon, within easy walking distance of Lithia Park and the Oregon Shakespeare Festival.
The self-catering property sleeps two guests in one bedroom with a queen-size bed, plus a sofa bed, and offers amenities including Wi-Fi, air conditioning, parking, and a barbecue in its outdoor seating area.
Redtail Inn - 3 Suites |  Sleeps Up To 12 - Ashland, OR
9.8 11 reviews
Ashland, OR
07/10 – 12/10
SG$1515/nighttotal: SG$7575 (5 )

Redtail Inn - 3 Suites | Sleeps Up To 12

1 4
B&B , Ashland
The Red Tail Inn is a charming farmhouse guesthouse located in downtown Ashland, just a short walk from the Oregon Shakespeare Festival theatres and the town's shops, restaurants, and coffeehouses. It's a convenient base for exploring the vibrant cultural scene of this historic town.
The inn offers three separate suites, each with its own bathroom and kitchenette, accommodating up to 12 guests. Guests can enjoy luxurious amenities such as double walk-in rain showers, granite countertops, and a shared hot tub, perfect for relaxing after a day of exploring.
Ashland's Premier Eco-b&b: Dog-friendly Queen Bed Room With Separate Entrance (Rosette) - Ashland, OR
Ashland, OR
18/09 – 20/09
SG$456/nighttotal: SG$912 (2 )

Ashland's Premier Eco-b&b: Dog-friendly Queen Bed Room With Separate Entrance (Rosette)

1 2
B&B , Ashland
This guest house is situated in Ashland's Siskiyou-Hargadine Historic District, just 366 meters from the Oregon Shakespeare Festival and close to the Oregon Cabaret Theatre.
This 335 square meter accommodation offers a dog-friendly 'Rosette' room for two guests, featuring garden access, air conditioning, internet, and a terrace, with gourmet breakfasts and free parking provided, all within reach of skiing and Weisinger Family Winery.
Ashland's Premier Eco-b&b: Dog-friendly Queen Bed Room With Separate Entrance (Pertelote) - Ashland, OR
Ashland, OR
18/09 – 20/09
SG$456/nighttotal: SG$912 (2 )

Ashland's Premier Eco-b&b: Dog-friendly Queen Bed Room With Separate Entrance (Pertelote)

1 2
B&B , Ashland
This Guest House is situated in Ashland's Siskiyou-Hargadine Historic District, 360 meters from the Oregon Shakespeare Festival and offering views of the Cascade Mountains.
With a floor area of 335 square meters, this establishment provides accommodation for two guests in one bedroom, featuring air conditioning, internet, a terrace, garden, pond, and dog-friendly facilities, with gourmet breakfasts and free parking available.
©2026 cozycozy.com