Ashland Hills Hotel & Suites offers a king-size bed guesthouse near downtown Ashland, Oregon, minutes from the Oregon Cabaret Theatre and Lithia Park. This pet-friendly hotel boasts a swimming pool, hot tub, fitness centre, and on-site restaurant, catering to couples with its one-bedroom, one-bathroom layout and capacity for two guests, plus access to various activities including bike rentals and live music.
9.2 669 reviews
Ashland, OR
18/09 – 20/09
NZ$670/nighttotal: NZ$1340 (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.
9.8 8 reviews
Ashland, OR
19/07 – 14/08
NZ$287/nighttotal: NZ$7462 (26 )
Queen Room W/common Bath
1 1
B&B , Ashland
The Columbia Hotel B&B, in Ashland's historic downtown, offers easy walking access to shops, restaurants, and theatres. This one-bedroom guesthouse provides a king-size Serta Serene™ Sky Plush bed, high-speed Wi-Fi, and shared private bathrooms with original porcelain sinks and cotton bathrobes for up to two guests, plus free entry to occasional live music events in the lobby.
Ashland, OR
15/10 – 19/10
NZ$655/nighttotal: NZ$2620 (4 )
Ashland's Premier Eco-b&b: Queen Bed Suite With Mountain Views (Fleur)
1 1
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.
9.8 26 reviews
Ashland, OR
19/07 – 14/08
NZ$266/nighttotal: NZ$6916 (26 )
Premium Bunk Room W/common Bath
1 1
B&B , Ashland
The El Tigre Room, a unique bunk room sleeping four adults, is situated in a 1910 building in Ashland, Oregon's downtown area, offering easy access to local attractions. This guesthouse features a shared private bathroom, antique furnishings, and sleep machines, alongside proximity to a bar and music lounge with live music (until 22:00) – note that access is via stairs only.
Ashland, OR
15/10 – 19/10
NZ$608/nighttotal: NZ$2432 (4 )
Ashland's Premier Eco-b&b: Dog-friendly Queen Bed Room With Separate Entrance (Rosette)
1 1
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.
9.9 220 reviews
Ashland, OR
15/10 – 19/10
NZ$234/nighttotal: NZ$936 (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.
9.5 31 reviews
Ashland, OR
08/08 – 10/08
NZ$254/nighttotal: NZ$508 (2 )
Ashland Motel, Two Queen Room
1 4
B&B , Ashland
This Ashland guesthouse, offering excellent guest ratings, provides a family-run experience with air conditioning, a saltwater pool, and parking; precise location within Ashland is unspecified, however. The self-catering unit features one bedroom, one bathroom, sleeps four, and includes amenities such as a refrigerator, microwave, and K-cup coffee maker.
9.9 214 reviews
Ashland, OR
15/10 – 19/10
NZ$204/nighttotal: NZ$816 (4 )
Wood Hamlet - Noble Forest Room Private By Downtn
1 1
B&B , Ashland
This Ashland guesthouse is situated 0.64 kilometres from the Oregon Shakespeare Festival and four blocks from Ashland's town centre, offering easy access to Lithia Park and numerous hiking and biking trails. The self-contained unit features a queen-sized bed, private bathroom, in-room coffee/tea making facilities, a mini-fridge, and access to a garden, patio, and swimming pond; it sleeps one guest.
9.8 195 reviews
Ashland, OR
15/10 – 19/10
NZ$412/nighttotal: NZ$1648 (4 )
The Billiard Room, Winner 2025 Best Of Ashland!
1 1
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.
9.8 37 reviews
Ashland, OR
15/10 – 19/10
NZ$522/nighttotal: NZ$2088 (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.
9.8 11 reviews
Ashland, OR
07/10 – 12/10
NZ$2027/nighttotal: NZ$10135 (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.
Best Ashland, OR bed and breakfasts with breakfast included
9.8 37 reviews
Ashland, OR
15/10 – 19/10
NZ$522/nighttotal: NZ$2088 (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.
9.2 669 reviews
Ashland, OR
18/09 – 20/09
NZ$670/nighttotal: NZ$1340 (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
10 1 review
Ashland, OR
08/08 – 10/08
NZ$554/nighttotal: NZ$1108 (2 )
Ashland 2 Double Suite W/gym & Pool
1 4
B&B , Ashland
This bed and breakfast is located near the Rogue Valley, just a few minutes from Ashland town centre, offering convenient access to local attractions such as the Oregon Shakespeare Festival (a 13-minute walk) and Mount Ashland Ski Area (a 39-kilometre drive). This pet-friendly guest house provides a private one-bedroom suite for up to four guests, featuring air conditioning, a kitchenette with a full-size fridge and microwave, a swimming pool, a hot tub, and a 24-hour fitness centre, with cooked-to-order breakfast available for an additional charge.
9.8 146 reviews
Ashland, OR
15/10 – 19/10
NZ$287/nighttotal: NZ$1148 (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.
9.5 30 reviews
Ashland, OR
08/08 – 10/08
NZ$338/nighttotal: NZ$676 (2 )
Ashland Abode | Swim. Ski Nearby.
1 4
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.
9.4 204 reviews
Ashland, OR
08/08 – 10/08
NZ$317/nighttotal: NZ$634 (2 )
Peace And Joy Mini Farm
2 4
gîte , Ashland
This Ashland countryside self-catering property is located 5 minutes (approximately 8km) from Ashland's town centre, providing easy access to the Oregon Shakespeare Festival and within a short drive of Mount Ashland Ski Area. This pet-friendly holiday home offers two bedrooms, one bathroom, sleeping up to four guests, and features a mini-farm, BBQ area, on-site beauty salon, free parking, and excellent guest reviews.
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, you can't miss the Oregon Shakespeare Festival, the heart of Ashland's cultural scene. The Lithia Park is also a must-see, with its beautiful gardens and walking paths. And don't forget to take a stroll down the historic Main Street, 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 enjoys a Mediterranean climate, with warm, dry summers and mild, wet winters. You'll find plenty of sunshine for hiking in the summer, but be prepared for rain in the winter months. Spring and autumn are ideal times for exploring nature, with pleasant temperatures and beautiful foliage.
What are the best bed and breakfasts with a pool in Ashland, OR?
What outdoor activities can visitors enjoy in and around Ashland, OR?
Ashland is a nature lover's paradise! You can hike in the Siskiyou Mountains, go fishing on the Rogue River, or take a scenic drive through the Cascade-Siskiyou National Monument. For a more leisurely experience, enjoy a picnic at the Lithia Park or take a bike ride along the Bear Creek Greenway.
What are the best bed and breakfasts with a jacuzzi in Ashland, OR?
What famous cities can be easily accessed from Ashland, OR?
Ashland is conveniently located near several popular destinations. You can easily drive to Medford, about 20 minutes away, which offers more shopping and dining options. For a longer trip, you can visit Crater Lake National Park, about 2 hours away, or the city of Portland, about 4 hours away.
What are the best bed and breakfasts for families and kids in Ashland, OR?
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.
9.7 158 reviews
Ashland, OR
15/10 – 19/10
NZ$499/nighttotal: NZ$1996 (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.
Ashland, OR
08/08 – 10/08
NZ$490/nighttotal: NZ$980 (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.
9.3 70 reviews
Ashland, OR
15/10 – 19/10
NZ$379/nighttotal: NZ$1516 (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.
Best Ashland, OR bed and breakfasts with air conditioning
Ashland, OR
19/07 – 14/08
NZ$559/nighttotal: NZ$14534 (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.
Ashland, OR
19/07 – 14/08
NZ$460/nighttotal: NZ$11960 (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.
Ashland, OR
19/07 – 14/08
NZ$483/nighttotal: NZ$12558 (26 )
Ashland 2 Queen Studio W/gym, Pool
1 1
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.
9.8 66 reviews
Ashland, OR
08/08 – 10/08
NZ$586/nighttotal: NZ$1172 (2 )
Redtail Inn - Orliena Suite | Hot Tub | Dtwn
1 4
B&B , Ashland
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.