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.
10 1 review
Ashland, OR
26/08 – 27/08
SG$505/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.
9.9 214 reviews
Ashland, OR
15/10 – 19/10
SG$153/nighttotal: SG$612 (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.
9.2 669 reviews
Ashland, OR
04/08 – 06/08
SG$415/nighttotal: SG$830 (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.
9.1 7 reviews
Ashland, OR
10/07 – 12/07
SG$236/nighttotal: SG$472 (2 )
Premium King Room W/common Bath
1 2
B&B , Ashland
The Columbia Hotel B&B, situated in Ashland's downtown area on the second floor of the historic 1910 Enders Building, offers easy access to shops, restaurants, theatres, Lithia Park, and the Oregon Shakespeare Festival. This guest house features a spacious Premium King Room (over 18.6 square metres), accommodating two guests, with a Serta Serene™ Sky Plush King bed, complimentary Wi-Fi, parking, and occasional free live music in the lobby.
9.8 8 reviews
Ashland, OR
19/07 – 14/08
SG$215/nighttotal: SG$5590 (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.
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.
9.8 195 reviews
Ashland, OR
15/10 – 19/10
SG$308/nighttotal: SG$1232 (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.
9.7 158 reviews
Ashland, OR
04/08 – 06/08
SG$373/nighttotal: SG$746 (2 )
Abigail's Bed And Breakfast Inn
1 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.
10 11 reviews
Ashland, OR
10/07 – 12/07
SG$332/nighttotal: SG$664 (2 )
Shrews House, Baroque Room
1 2
B&B , Ashland
Shrews House, a guesthouse in a central Ashland location, offers convenient access to Ashland's attractions, though precise distances aren't specified. This one-bedroom, one-bathroom lodging sleeps two guests, boasting completely remodelled rooms with new wood floors, a private bathroom, air conditioning, parking, a swimming pool, and excellent guest ratings.
9.5 30 reviews
Ashland, OR
10/07 – 12/07
SG$309/nighttotal: SG$618 (2 )
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.
9.9 148 reviews
Ashland, OR
04/08 – 06/08
SG$193/nighttotal: SG$386 (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.
Best Ashland, OR bed and breakfasts with breakfast included
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
Ashland, OR
10/07 – 12/07
SG$366/nighttotal: SG$732 (2 )
Ashland Retreat | Tennis. Pool.
1 2
B&B , Ashland
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.
9.3 343 reviews
Ashland, OR
26/08 – 27/08
SG$516/nightfor 1 night
Arden Forest Inn
2 3
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
15/10 – 19/10
SG$490/nighttotal: SG$1960 (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.
Ashland, OR
10/07 – 12/07
SG$440/nighttotal: SG$880 (2 )
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.
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 in Ashland, you've got to see the Oregon Shakespeare Festival, a renowned theatre company, and the Lithia Park, a beautiful green space with a creek running through it. You can also explore 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, meaning warm, dry summers and mild, wet winters. You'll find the best weather for exploring nature in the spring and autumn. Be sure to pack layers, as the temperature can vary throughout the day.
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. You can go hiking in the Siskiyou Mountains, go fishing in the Rogue River, or explore the many parks and trails in the area. The Cascade Siskiyou National Monument is a must-visit for outdoor enthusiasts.
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 a great base for exploring the region. You can easily drive to Medford, a larger city about 20 minutes away, or to Crater Lake National Park, a stunning volcanic crater lake about 2 hours away. For a longer trip, you can head to the coast, about 3 hours away.
What are the best bed and breakfasts for families and kids in Ashland, OR?
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
04/08 – 06/08
SG$347/nighttotal: SG$694 (2 )
Sunset Cottage At Grizzly Peak Winery
1 2
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
9.8 66 reviews
Ashland, OR
04/08 – 06/08
SG$255/nighttotal: SG$510 (2 )
Redtail Inn - Orliena Suite | Hot Tub | Dtwn
1 2
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.
Chanticleer Inn, a pet-friendly guesthouse in a quiet Ashland residential neighbourhood, is situated 0.3km from Ashland's city centre and 0.6km from the Oregon Shakespeare Festival. This eco-friendly, Craftsman-style house offers a King room with a private entrance and fireplace, accommodating up to three guests, and features pollinator gardens, a pond, yoga platforms, a fire pit, Cascades views, and seasonal gourmet breakfasts (March 15th - October 15th), plus free Wi-Fi and parking.
8.9 13 reviews
Ashland, OR
19/07 – 14/08
SG$277/nighttotal: SG$7202 (26 )
Respite In Oregon | Swim. Cafe.
1 1
B&B , Ashland
Ashland Hills Hotel & Suites offers a convenient base near downtown Ashland, Oregon, approximately 14.5km from the Oregon Cabaret Theatre, 21km from Lithia Park, and 46.7km from Mount Ashland Ski Area. This pet-friendly guesthouse features a king-size bed, separate living area, on-site pool, fitness centre, and parking, accommodating up to two guests, with added benefits such as bike rentals and access to a spa and laundry facilities.
9.8 70 reviews
Ashland, OR
04/08 – 06/08
SG$226/nighttotal: SG$452 (2 )
Redtail Inn - Louisa Suite | Hot Tub |Dwtn
1 2
B&B , Ashland
The Red Tail Inn is a charming guesthouse in downtown Ashland, just a short walk from the Oregon Shakespeare Festival and the city's main attractions. This highly rated inn consistently receives excellent reviews for its location, cleanliness, and overall experience. The Louisa McCall Suite can accommodate up to two guests and features a full kitchen, a private hot tub, and a luxurious bathroom with a double walk-in shower. Guests can enjoy a range of amenities, including a Tesla charging station, a garden, and a pet-friendly policy for those travelling with their furry companions.