Bed and Breakfast and Inn in Stockbridge, MA

14 available b&b offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Stockbridge, MA B&B
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

14 Bed and Breakfasts and Inn in Stockbridge, MA

Best Stockbridge, MA bed and breakfasts with breakfast included

Whistler's Inn - Stockbridge, MA
8.0 647 reviews
Stockbridge, MA
14/10 – 21/10
$545/nighttotal: $3815 (7 )

Whistler's Inn

1 4
B&B , Lenox
The Whistler's Inn is a charming bed and breakfast situated in Lenox, Massachusetts, a short distance from Tanglewood Musical Center and Shakespeare & Company Theater. The inn has consistently received very good user ratings for its cleanliness and excellent location.
Each room at the inn has a unique style and features a private bathroom. Guests can enjoy a daily gourmet breakfast, afternoon tea and cookies, and have access to a parlour room with a piano and a library. The inn also has a garden and a terrace, and guests can enjoy free Wi-Fi and parking.
Eastgate Inn B&b - Stockbridge, MA
9.3 92 reviews
Stockbridge, MA
14/10 – 21/10
$723/nighttotal: $5061 (7 )

Eastgate Inn B&b

2 4
B&B , Lenox
This charming bed and breakfast is located in the mountains of Lenox, just a short drive from popular attractions like Shakespeare and Company, The Mount, and Kennedy Park. It has received excellent reviews from previous guests.
The accommodation offers a peaceful retreat with a beautiful garden and a cosy library. Guests can enjoy a continental breakfast, free Wi-Fi, and free parking, as well as barbecue facilities and a fireplace in the lobby.

Best Stockbridge, MA bed and breakfasts with a garden

Terrace Suite In Five-star Hotel - Stockbridge, MA
Stockbridge, MA
23/06 – 28/06
$18463/nighttotal: $92315 (5 )

Terrace Suite In Five-star Hotel

1 2
B&B , Stockbridge
This Stockbridge guesthouse offers a ground-floor suite with mountain views, a 40-foot private covered terrace, and is situated a short drive from Stockbridge's attractions, the precise location unspecified.
The self-catering unit features a king-size bed, a BeoVision 7-40 entertainment system, an antique soaking tub, and a large shower, accommodating up to two guests.

Frequently Asked Questions about bed and breakfast in Stockbridge, MA

  • What are the must-see sights for first-time visitors on a day trip to Stockbridge, MA region?

    For a first-time visit, you definitely want to see the Norman Rockwell Museum, which showcases his iconic American art. Then, head over to the beautiful Tanglewood Music Center to enjoy the stunning architecture and the serene atmosphere, especially if there's a concert happening. You can also pop into the Stockbridge Library, a charming building with a rich history.
  • What are the best bed and breakfasts in Stockbridge, MA?

  • What weather can travelers expect when exploring nature in Stockbridge, MA?

    Stockbridge has four distinct seasons. Summers are warm and humid, perfect for hiking and exploring the Berkshires. Autumn is a beautiful time with vibrant foliage. Winters are cold and snowy, ideal for skiing and snowshoeing. Spring brings mild temperatures and blooming flowers, making it a great time for walks in the countryside.
  • What are the best bed and breakfasts with a pool in Stockbridge, MA?

  • What outdoor activities can visitors enjoy in and around Stockbridge, MA?

    Stockbridge is a great place for outdoor activities. You can hike the trails of the Mount Everett State Forest, go kayaking on the Stockbridge Bowl, or visit the Chesterwood, the former estate of sculptor Daniel Chester French, and explore its beautiful gardens. And don't forget to visit the Naumkeag estate, a stunning example of American architecture and gardens.
  • What are the best bed and breakfasts for families and kids in Stockbridge, MA?

    The best B&B for families and kids in Stockbridge, MA is The Cottage.

  • What famous cities can be easily accessed from Stockbridge, MA?

    Stockbridge is conveniently located near several famous cities. You can easily reach Boston, New York City, and Albany by car, all within a few hours' drive. And if you're looking for a shorter trip, Pittsfield is just a short drive away and offers a variety of attractions.
  • What are the best pet friendly bed and breakfasts in Stockbridge, MA?

  • What local breakfast specialties can you enjoy in Stockbridge, MA region?

    Stockbridge has some great breakfast spots. The Red Lion Inn is a classic choice, known for its hearty breakfasts. The Allium Restaurant offers a more modern take on breakfast, with fresh and seasonal ingredients. And for a quick and delicious bite, try the Stockbridge Coffee & Tea, a local favourite for coffee and pastries.
  • What are the best bed and breakfasts with parking in Stockbridge, MA?

Destinations nearby

Best Stockbridge, MA bed and breakfasts with parking

Eastgate Inn B&b - Stockbridge, MA
9.3 92 reviews
Stockbridge, MA
14/10 – 21/10
$723/nighttotal: $5061 (7 )

Eastgate Inn B&b

2 4
B&B , Lenox
This charming bed and breakfast is located in the mountains of Lenox, just a short drive from popular attractions like Shakespeare and Company, The Mount, and Kennedy Park. It has received excellent reviews from previous guests.
The accommodation offers a peaceful retreat with a beautiful garden and a cosy library. Guests can enjoy a continental breakfast, free Wi-Fi, and free parking, as well as barbecue facilities and a fireplace in the lobby.
The Cornell Inn, Lenox & The Berkshires - Stockbridge, MA
9.1 1529 reviews
Stockbridge, MA
23/06 – 28/06
$675/nighttotal: $3375 (5 )

The Cornell Inn, Lenox & The Berkshires

1 2
B&B , Lenox
This charming bed and breakfast is situated in Lenox, just a short distance from the Boston Symphony Orchestra's Tanglewood Institute, and within easy reach of the town's restaurants. It boasts excellent user, location, and cleanliness ratings, making it a popular choice for travellers seeking a comfortable and enjoyable stay.
The guest house is set on four acres, offering a peaceful and secluded environment. Guests can enjoy a gourmet breakfast, relax on the private deck, or explore the gardens that connect to Kennedy Park.
Shaker Mill Inn - Stockbridge, MA
9.5 562 reviews
Stockbridge, MA
14/10 – 21/10
$377/nighttotal: $2639 (7 )

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.
Whistler's Inn - Stockbridge, MA
8.0 647 reviews
Stockbridge, MA
14/10 – 21/10
$545/nighttotal: $3815 (7 )

Whistler's Inn

1 4
B&B , Lenox
The Whistler's Inn is a charming bed and breakfast situated in Lenox, Massachusetts, a short distance from Tanglewood Musical Center and Shakespeare & Company Theater. The inn has consistently received very good user ratings for its cleanliness and excellent location.
Each room at the inn has a unique style and features a private bathroom. Guests can enjoy a daily gourmet breakfast, afternoon tea and cookies, and have access to a parlour room with a piano and a library. The inn also has a garden and a terrace, and guests can enjoy free Wi-Fi and parking.

Best Stockbridge, MA bed and breakfasts with air conditioning

Bright 2br Condo – Perfect For Family Or Friends - Stockbridge, MA
Stockbridge, MA
23/06 – 28/06
$495/nighttotal: $2475 (5 )

Bright 2br Condo – Perfect For Family Or Friends

1 2
B&B , Lee
This B&B is located in the Berkshires, offering a New England feel and easy access to mountain activities.
Accommodating up to six guests in two bedrooms with two bathrooms, this establishment provides a fully equipped kitchen, indoor and outdoor swimming pools, a hot tub, a cinema, a bar, and complimentary parking.
Standard Queen - Stockbridge, MA
Stockbridge, MA
23/06 – 28/06
$229/nighttotal: $1145 (5 )

Standard Queen

1 2
B&B , Lee
The Pilgrim Inn, a guesthouse in Lee, Massachusetts, offers convenient access to Berkshire attractions.
This one-bedroom, one-bathroom lodging sleeps two guests and includes amenities such as air conditioning, parking, and internet access.
The Cornell Inn Lenox - Stockbridge, MA
Stockbridge, MA
23/06 – 28/06
$1230/nighttotal: $6150 (5 )

The Cornell Inn Lenox

1 2
B&B , Lenox
The Cornell Inn, a historic 28-room guesthouse, is centrally located in Lenox, Massachusetts, a short distance (less than 1.6km) from Tanglewood and other Berkshire attractions.
This one-bedroom, one-bathroom lodging offers accommodation for up to three guests, including a delicious breakfast, air conditioning, parking, internet access, and serene gardens; nearby hiking trails and Lenox's cultural attractions provide ample activities.
Cozy 2-bedroom Apartment With Ac, Fitness Room - Stockbridge, MA
10 9 reviews
Stockbridge, MA
14/10 – 21/10
$344/nighttotal: $2408 (7 )

Cozy 2-bedroom Apartment With Ac, Fitness Room

1 4
B&B , Lee
This Lee, Berkshire guesthouse offers self-catering apartments, each spanning 76 square metres, with easy access to the Berkshires mountain trails.
Each apartment boasts two bedrooms, two bathrooms, sleeps six guests, and includes a fully equipped kitchen, air conditioning, a swimming pool, a jacuzzi, and a fitness centre; the resort also features a bar and family amenities such as indoor and outdoor pools, a cinema, and mini-golf.
©2026 cozycozy.com