The Red Tail Inn is a charming guesthouse located in the heart of downtown Ashland, just a short walk from the Oregon Shakespeare Festival theatres, shops, and restaurants. It has consistently received excellent ratings for its location, cleanliness, and overall experience. The guesthouse offers a one-bedroom suite that can accommodate up to four guests. It features a comfortable living and dining area, a luxurious bathroom with a walk-in shower, and a kitchenette with essential amenities. Guests can also enjoy a private hot tub, a garden, and parking, as well as access to a Tesla charging station.
9.8 23 reviews
Ashland, OR
03/07 – 06/07
915 ﺩ.ﺇ/nighttotal: 2745 ﺩ.ﺇ (3 )
Shrews House, Mt. Ashland Room
1 2
B&B , Ashland
This Ashland guesthouse, near Mount Ashland, offers convenient access to the mountain's attractions; precise distances to other Ashland landmarks require further clarification. The single-bedroom, en-suite guest house sleeps two, boasting a private porch overlooking the pool, a rustic interior with Ashland memorabilia, a stone fireplace, air conditioning, a queen-sized bed, and a claw-foot soaking tub; on-site parking is also available.
9.8 37 reviews
Ashland, OR
15/10 – 19/10
1114 ﺩ.ﺇ/nighttotal: 4456 ﺩ.ﺇ (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.
9.7 158 reviews
Ashland, OR
20/08 – 22/08
2212 ﺩ.ﺇ/nighttotal: 4424 ﺩ.ﺇ (2 )
Abigail's Bed And Breakfast Inn
2 2
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.
Ashland, OR
15/10 – 19/10
1220 ﺩ.ﺇ/nighttotal: 4880 ﺩ.ﺇ (4 )
Ashland's Premier Eco-b&b: Queen Bed Room With Garden Views (Maitre)
1 1
B&B , Ashland
The Chanticleer Inn, a bed and breakfast, is situated within Ashland's historic Siskiyou-Hargadine district, 365 metres from the Oregon Shakespeare Festival and Oregon Cabaret Theatre. This 1920s Craftsman property offers six en-suite rooms, accommodating up to two guests, and boasts extensive gardens with a pond, complemented by amenities such as free parking, wifi, and air conditioning.
9.9 148 reviews
Ashland, OR
04/08 – 06/08
553 ﺩ.ﺇ/nighttotal: 1106 ﺩ.ﺇ (2 )
Summer’s Night Cottage 8 Minute Walk To Downtown
1 2
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.
10 1 review
Ashland, OR
25/08 – 26/08
1442 ﺩ.ﺇ/nightfor 1 night
Ashland's Premier Eco-b&b: Dog-friendly King Bed Suite With Separate Entrance (Jardin)
1 3
B&B , Ashland
This guest house is located in Ashland's Siskiyou-Hargadine Historic District, 400 metres from the Oregon Shakespeare Festival and offering views of the Cascade Mountains. The property boasts extensive gardens, a tranquil pond, and the dog-friendly 'Jardin' suite, which sleeps three guests and includes a king bed, sleeper sofa, gas fireplace, and separate entrance, with gourmet breakfasts and free parking provided.
9.3 343 reviews
Ashland, OR
20/08 – 22/08
754 ﺩ.ﺇ/nighttotal: 1508 ﺩ.ﺇ (2 )
Arden Forest Inn
1 2
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, OR
03/07 – 06/07
1134 ﺩ.ﺇ/nighttotal: 3402 ﺩ.ﺇ (3 )
Ashland 2 Queen Studio W/gym, Pool
1 2
B&B , Ashland
This studio apartment is situated near the Rogue Valley, offering convenient access to downtown Ashland and attractions such as the Oregon Shakespeare Festival, located 7 minutes away by car, and Lithia Park, also a 7-minute drive. This pet-friendly accommodation, with a fee for non-service animals, features a private suite with two queen beds, a workstation, a full bathroom, and includes access to a 24-hour fitness centre, an outdoor swimming pool, a hot tub, and complimentary bicycle rentals.
10 1 review
Ashland, OR
10/07 – 12/07
713 ﺩ.ﺇ/nighttotal: 1426 ﺩ.ﺇ (2 )
Bunk Room W/common Bath
1 2
B&B , Ashland
The Columbia Hotel B&B, a guesthouse in Ashland, Oregon, is situated on the second floor of a historic building in downtown Ashland, offering easy access to local attractions. This pet-friendly lodging features one bedroom, two bathrooms, sleeps four guests in comfortable bunk rooms with Twin XL Suite Sleep™ Lassen Luxury Mattresses, and includes a relaxing lounge area with complimentary beer and fast Wi-Fi.
Ashland, OR
20/08 – 22/08
1232 ﺩ.ﺇ/nighttotal: 2464 ﺩ.ﺇ (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.
Ashland, OR
25/08 – 26/08
1442 ﺩ.ﺇ/nightfor 1 night
Ashland's Premier Eco-b&b: King Bed Suite With Mountain Views (Aerie)
1 3
B&B , Ashland
This guest house is situated in Ashland's Siskiyou-Hargadine Historic District, just 365 metres from the Oregon Shakespeare Festival and close to North Mountain Park. The Chanticleer Inn offers 335 square metres of space, accommodating up to three guests with one bedroom and one bathroom, and features extensive gardens with a pond and views of the Cascade mountains.
Best Ashland, OR bed and breakfasts with breakfast included
9.2 669 reviews
Ashland, OR
18/09 – 20/09
1431 ﺩ.ﺇ/nighttotal: 2862 ﺩ.ﺇ (2 )
Mccall House Boutique Inn
1 2
B&B , Ashland
This charming guesthouse is located in Ashland's Historic Downtown District, just a short walk from Lithia Park and Thomas Theatre, with the Oregon Shakespeare Festival and Oregon Cabaret Theatre a 10-minute walk away. The B&B has consistently received excellent ratings for its location, cleanliness, and overall experience. The guest house features a shared space with a coffee/tea station, a microwave, and a refrigerator, perfect for a quick bite or a relaxing break. Guests can enjoy a complimentary full breakfast each morning, along with free Wi-Fi, self-parking, and a manager's reception, making it a great base for exploring Ashland's attractions.
Best Ashland, OR bed and breakfasts with a garden
9.5 59 reviews
Ashland, OR
03/07 – 06/07
650 ﺩ.ﺇ/nighttotal: 1950 ﺩ.ﺇ (3 )
The Artist’s Overlook — Walk To Town
1 2
B&B , Ashland
This Ashland studio apartment is situated near Ashland Hills, a 0.8-kilometre walk from the Oredson Todd Woods trail network, offering easy access to Lithia Park and Mount Ashland. The self-contained unit features a queen-sized bed, a well-equipped kitchenette with a smart oven, and access to outdoor decks and a gas grill; it sleeps two guests and boasts new hickory hardwood floors.
Ashland, OR
25/08 – 26/08
1442 ﺩ.ﺇ/nightfor 1 night
Ashland's Premier Eco-b&b: Queen Bed Suite With Mountain Views (Fleur)
1 3
B&B , Ashland
This guest house is situated in Ashland's Siskiyou-Hargadine Historic District, 365 metres from the Oregon Shakespeare Festival, offering views of the Cascade mountains and extensive gardens with a pond. The property provides six en-suite rooms, including a suite with a sleeper sofa, accommodating up to three guests, and features complimentary parking, Wi-Fi, and air conditioning, with a floor area of 335 square metres.
9.3 70 reviews
Ashland, OR
04/08 – 06/08
1127 ﺩ.ﺇ/nighttotal: 2254 ﺩ.ﺇ (2 )
The Matriarch Suites- Downtown Ashland, Or
1 2
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.
Ashland, OR
19/07 – 14/08
982 ﺩ.ﺇ/nighttotal: 25532 ﺩ.ﺇ (26 )
Ashland King Studio W/gym & Pool
1 1
B&B , Ashland
This guest house in Ashland is located near the Rogue Valley, a short drive from the town centre, offering convenient access to the Oregon Shakespeare Festival (approximately 1.5 kilometres away) and Southern Oregon University (approximately 500 metres away). The accommodation provides a private suite for two guests, featuring a king-size bed, air conditioning, Wi-Fi, a swimming pool, a hot tub, a fitness centre, and complimentary on-site parking, with a daily cooked breakfast available for an extra charge.
Frequently Asked Questions about bed and breakfast in Ashland, OR
What are the must-see sights for first-time visitors on a day trip to Ashland, OR region?
For a day trip to Ashland, you should definitely see the Oregon Shakespeare Festival, the Lithia Park with its stunning views, and the historic downtown area with its charming shops and restaurants.
What are the best bed and breakfasts in Ashland, OR?
What weather can travelers expect when exploring nature in Ashland, OR?
Ashland has a Mediterranean climate with warm, dry summers and mild, wet winters. You can expect temperatures to range from 10 to 30 degrees Celsius, with plenty of sunshine. The best time to explore nature is in the spring or autumn when the weather is pleasant and the crowds are smaller.
What are the best bed and breakfasts with a pool in Ashland, OR?
What outdoor activities can visitors enjoy in and around Ashland, OR?
There are plenty of outdoor activities to enjoy in and around Ashland, including hiking in the Siskiyou Mountains, fishing in the Rogue River, and biking on the Bear Creek Greenway. You can also visit the nearby Crater Lake National Park, a stunning volcanic caldera filled with crystal-clear water.
What are the best bed and breakfasts with a jacuzzi in Ashland, OR?
What local breakfast specialties can you enjoy in Ashland, OR region?
Ashland is known for its delicious breakfast options. Some local favourites include the biscuits and gravy at the Ashland Coffee & Tea, the pancakes at the Morning Glory Cafe, and the breakfast burritos at the Black Sheep Cafe.
What are the best bed and breakfasts for families and kids in Ashland, OR?
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
9.8 195 reviews
Ashland, OR
04/08 – 06/08
836 ﺩ.ﺇ/nighttotal: 1672 ﺩ.ﺇ (2 )
The Billiard Room, Winner 2025 Best Of Ashland!
1 2
B&B , Ashland
The Ashland Carter House B&B is located in the historic downtown district of Ashland, within easy walking distance of the Ashland Shakespeare Festival and other attractions. The property has received excellent ratings for location, cleanliness, and overall user experience. The Billiard Room is a private, self-contained unit within the main house, suitable for two guests. It features a kitchenette, a comfortable queen-sized bed, a private bathroom, and access to the garden, patio, and swimming pool during the summer months.
Ashland, OR
19/07 – 14/08
1193 ﺩ.ﺇ/nighttotal: 31018 ﺩ.ﺇ (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.
8.0 5 reviews
Ashland, OR
03/07 – 06/07
738 ﺩ.ﺇ/nighttotal: 2214 ﺩ.ﺇ (3 )
Ashland Motel, Two Queen Suite
1 2
B&B , Ashland
This Ashland guesthouse, offering a very good user rating, is conveniently located in Ashland (precise location within Ashland requires further clarification); information regarding proximity to specific Ashland landmarks is unavailable. The self-catering property features one bedroom, one bathroom, sleeps four guests, and includes air conditioning, a swimming pool, parking, and free Wi-Fi; further details on interior design and the property's size are not provided.
9.5 30 reviews
Ashland, OR
03/07 – 06/07
781 ﺩ.ﺇ/nighttotal: 2343 ﺩ.ﺇ (3 )
Ashland Abode | Swim. Ski Nearby.
1 2
B&B , Ashland
Ashland Hills Hotel & Suites offers a convenient base near downtown Ashland, Oregon, within easy driving distance (a few kilometres) of the Oregon Cabaret Theatre and Lithia Park. This pet-friendly guesthouse features a one-bedroom suite sleeping four, complete with a private bathroom, kitchen facilities (fridge, freezer, microwave), a swimming pool, jacuzzi, fitness centre and free Wi-Fi; additional paid activities such as bike tours are available.