2 Family-friendly Villas L Pool, Games & Whirlpool
4 4
B&B , Lee
This Bed and Breakfast is situated in the Berkshires, offering convenient access to outdoor pursuits such as hiking, boating, and skiing, with the Appalachian Trail just a short distance away, and is located within 2 kilometres of the Norman Rockwell Museum and Tanglewood. Each of the four spacious 94.4 square metre bedrooms accommodates up to three guests and includes a private bathroom, air conditioning, complimentary toiletries, a fridge, microwave, and dishwasher, with guests also able to enjoy the on-site indoor heated swimming pool and public fitness centre.
9.5 92 reviews
Great Barrington, MA
15/08 – 20/08
NZ$1009/nightTotal: NZ$5045 (5 )
Wilder House Berkshires
2 4
B&B , Sheffield
Wilder House Berkshires, a guesthouse in Sheffield, Massachusetts, is situated approximately 9.6km from Great Falls and 10km from the Canaan Village Historic District, offering easy access to Berkshire attractions. This one-bedroom, one-bathroom lodging boasts air conditioning, a terrace, a garden, free parking, and Wi-Fi; a daily American breakfast is included.
9.5 559 reviews
Great Barrington, MA
02/07 – 06/07
NZ$880/nightTotal: NZ$3520 (4 )
Shaker Mill Inn
1 4
B&B , West Stockbridge
Shaker Mill Inn is situated in West Stockbridge, just under 6.5 kilometres from Tanglewood and the Norman Rockwell Museum. The inn has consistently received excellent ratings for location, cleanliness and overall experience. The inn offers a range of rooms, all with en-suite facilities. Guests can enjoy a continental breakfast, relax in the garden or by the outdoor fireplace, and take advantage of the on-site spa, Jacuzzi and massage services.
Great Barrington, MA
02/07 – 06/07
NZ$1209/nightTotal: NZ$4836 (4 )
Family Basecamp | 3 Villas, Pools & Games
6 4
B&B , Lee
This B&B in Lee is situated in the Berkshires, offering convenient access to hiking, boating, and skiing, with the Norman Rockwell Museum, Tanglewood, and the Appalachian Trail all within a 5-kilometre radius. Each of the six spacious rooms, covering 95 square metres, accommodates up to three guests and features complimentary toiletries, basic kitchen facilities, and HD televisions, alongside access to a shared fitness centre and heated indoor pool.
9.6 405 reviews
Great Barrington, MA
24/07 – 26/07
NZ$7400/nightTotal: NZ$14800 (2 )
Chambery Inn
5 10
B&B , Lee
The Chambery Inn is situated in Lee, Massachusetts, a short drive from both the Berkshire Scenic Railroad Museum and Tanglewood Musical Center, making it an ideal base for exploring the area's attractions. The inn has consistently received excellent ratings for its location, cleanliness, and overall experience. This former schoolhouse has been transformed into a charming guesthouse with a unique design, featuring individual room styles and special features. Guests can enjoy a continental breakfast delivered to their room, relax in the garden, take advantage of the spa, and enjoy the nearby Ski Butternut resort for winter sports.
Great Barrington, MA
02/07 – 06/07
NZ$1612/nightTotal: NZ$6448 (4 )
Villa Retreat | Four Rooms, Sauna, Courts & Bbq
8 4
B&B , Lee
This guest house is situated in the Berkshires, offering easy access to outdoor pursuits and cultural sites such as the Norman Rockwell Museum and Tanglewood, with the Appalachian Trail only 1.6 kilometres away. With 8 bedrooms and 8 bathrooms, this property can accommodate up to 24 guests across 94 square metres, featuring a kitchen with a fridge, microwave, and dishwasher, as well as air conditioning, an indoor heated swimming pool, and a public fitness centre.
Great Barrington, MA
02/07 – 06/07
NZ$1209/nightTotal: NZ$4836 (4 )
Three 2br Villas W/ Sauna, Games & Pool Access
6 4
B&B , Lee
This guest house in the Berkshires, Lee, offers proximity to the Appalachian Trail, hiking, boating, skiing, the Norman Rockwell Museum and Tanglewood. Boasting six bedrooms and six bathrooms to accommodate up to 18 guests, this establishment features air conditioning, Wi-Fi, a swimming pool, a garden, a fitness centre, and rooms with basic kitchen amenities and high-definition televisions.
Great Barrington, MA
02/07 – 06/07
NZ$1612/nightTotal: NZ$6448 (4 )
Four Villas L Arcade, Pool & Forest Views Awaits
8 4
B&B , Lee
This Bed and Breakfast is located in the Berkshires, offering convenient access to outdoor pursuits and cultural sites such as the Norman Rockwell Museum and Tanglewood. With 8 bedrooms and 8 bathrooms accommodating up to 24 guests, this property features spacious rooms of approximately 94 square meters, complete with a fridge, microwave, and dishwasher, alongside access to a shared fitness centre and a heated indoor swimming pool.
Best Great Barrington, MA bed and breakfasts with breakfast included
9.5 559 reviews
Great Barrington, MA
02/07 – 06/07
NZ$880/nightTotal: NZ$3520 (4 )
Shaker Mill Inn
1 4
B&B , West Stockbridge
Shaker Mill Inn is situated in West Stockbridge, just under 6.5 kilometres from Tanglewood and the Norman Rockwell Museum. The inn has consistently received excellent ratings for location, cleanliness and overall experience. The inn offers a range of rooms, all with en-suite facilities. Guests can enjoy a continental breakfast, relax in the garden or by the outdoor fireplace, and take advantage of the on-site spa, Jacuzzi and massage services.
9.5 92 reviews
Great Barrington, MA
15/08 – 20/08
NZ$1009/nightTotal: NZ$5045 (5 )
Wilder House Berkshires
2 4
B&B , Sheffield
Wilder House Berkshires, a guesthouse in Sheffield, Massachusetts, is situated approximately 9.6km from Great Falls and 10km from the Canaan Village Historic District, offering easy access to Berkshire attractions. This one-bedroom, one-bathroom lodging boasts air conditioning, a terrace, a garden, free parking, and Wi-Fi; a daily American breakfast is included.
Best Great Barrington, MA bed and breakfasts with a garden
Great Barrington, MA
02/07 – 06/07
NZ$1612/nightTotal: NZ$6448 (4 )
Villa Retreat | Four Rooms, Sauna, Courts & Bbq
8 4
B&B , Lee
This guest house is situated in the Berkshires, offering easy access to outdoor pursuits and cultural sites such as the Norman Rockwell Museum and Tanglewood, with the Appalachian Trail only 1.6 kilometres away. With 8 bedrooms and 8 bathrooms, this property can accommodate up to 24 guests across 94 square metres, featuring a kitchen with a fridge, microwave, and dishwasher, as well as air conditioning, an indoor heated swimming pool, and a public fitness centre.
9.6 405 reviews
Great Barrington, MA
24/07 – 26/07
NZ$7400/nightTotal: NZ$14800 (2 )
Chambery Inn
5 10
B&B , Lee
The Chambery Inn is situated in Lee, Massachusetts, a short drive from both the Berkshire Scenic Railroad Museum and Tanglewood Musical Center, making it an ideal base for exploring the area's attractions. The inn has consistently received excellent ratings for its location, cleanliness, and overall experience. This former schoolhouse has been transformed into a charming guesthouse with a unique design, featuring individual room styles and special features. Guests can enjoy a continental breakfast delivered to their room, relax in the garden, take advantage of the spa, and enjoy the nearby Ski Butternut resort for winter sports.
Great Barrington, MA
02/07 – 06/07
NZ$1209/nightTotal: NZ$4836 (4 )
Family Basecamp | 3 Villas, Pools & Games
6 4
B&B , Lee
This B&B in Lee is situated in the Berkshires, offering convenient access to hiking, boating, and skiing, with the Norman Rockwell Museum, Tanglewood, and the Appalachian Trail all within a 5-kilometre radius. Each of the six spacious rooms, covering 95 square metres, accommodates up to three guests and features complimentary toiletries, basic kitchen facilities, and HD televisions, alongside access to a shared fitness centre and heated indoor pool.
Great Barrington, MA
02/07 – 06/07
NZ$806/nightTotal: NZ$3224 (4 )
2 Family-friendly Villas L Pool, Games & Whirlpool
4 4
B&B , Lee
This Bed and Breakfast is situated in the Berkshires, offering convenient access to outdoor pursuits such as hiking, boating, and skiing, with the Appalachian Trail just a short distance away, and is located within 2 kilometres of the Norman Rockwell Museum and Tanglewood. Each of the four spacious 94.4 square metre bedrooms accommodates up to three guests and includes a private bathroom, air conditioning, complimentary toiletries, a fridge, microwave, and dishwasher, with guests also able to enjoy the on-site indoor heated swimming pool and public fitness centre.
Frequently asked questions about bed and breakfast in Great Barrington, MA
What are the must-see sights for first-time visitors on a day trip to Great Barrington, MA region?
For a day trip, you can't miss the iconic Monument Mountain, offering stunning views of the surrounding Berkshires. The historic Mahaiwe Performing Arts Center is a must for a cultural experience, and the vibrant shops and restaurants on Main Street are a delight to explore.
What are the best bed and breakfasts in Great Barrington, MA?
What weather can travelers expect when exploring nature in Great Barrington, MA?
The weather in Great Barrington is pretty varied, with hot, humid summers and cold, snowy winters. Spring and autumn are beautiful, with mild temperatures perfect for hiking and exploring the outdoors. Pack layers and be prepared for anything!
What are the best bed and breakfasts with a pool in Great Barrington, MA?
What outdoor activities can visitors enjoy in and around Great Barrington, MA?
Great Barrington is a haven for outdoor enthusiasts. Hiking trails abound in the nearby Mount Everett State Reservation, and the Housatonic River is perfect for kayaking and fishing. In the winter, cross-country skiing and snowshoeing are popular activities.
What are the best bed and breakfasts with a jacuzzi in Great Barrington, MA?
What local breakfast specialties can you enjoy in Great Barrington, MA region?
Start your day with a delicious breakfast at The Red Lion Inn, known for its traditional American breakfast fare. For something a little different, try the pancakes at The Barrington Coffee Roasters, a local favourite.
What are the best bed and breakfasts for families and kids in Great Barrington, MA?
Best pet friendly Great Barrington, MA bed and breakfasts
Among the 10 accommodations in Great Barrington, MA, here are the 1 best pet friendly B&Bs
9.5 559 reviews
Great Barrington, MA
02/07 – 06/07
NZ$880/nightTotal: NZ$3520 (4 )
Shaker Mill Inn
1 4
B&B , West Stockbridge
Shaker Mill Inn is situated in West Stockbridge, just under 6.5 kilometres from Tanglewood and the Norman Rockwell Museum. The inn has consistently received excellent ratings for location, cleanliness and overall experience. The inn offers a range of rooms, all with en-suite facilities. Guests can enjoy a continental breakfast, relax in the garden or by the outdoor fireplace, and take advantage of the on-site spa, Jacuzzi and massage services.
Best Great Barrington, MA bed and breakfasts with laundry available
9.6 405 reviews
Great Barrington, MA
24/07 – 26/07
NZ$7400/nightTotal: NZ$14800 (2 )
Chambery Inn
5 10
B&B , Lee
The Chambery Inn is situated in Lee, Massachusetts, a short drive from both the Berkshire Scenic Railroad Museum and Tanglewood Musical Center, making it an ideal base for exploring the area's attractions. The inn has consistently received excellent ratings for its location, cleanliness, and overall experience. This former schoolhouse has been transformed into a charming guesthouse with a unique design, featuring individual room styles and special features. Guests can enjoy a continental breakfast delivered to their room, relax in the garden, take advantage of the spa, and enjoy the nearby Ski Butternut resort for winter sports.