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Chambery Inn
3 out of 5
199 Main St, Lee, MA
Fully refundableReserve now, pay when you stay
The price is $200 per night from Aug 25 to Aug 25
Located in the heart of Lee, this bed & breakfast is within a 5-minute walk of Animagic Museum of Animation and Lee Library. Housatonic River and Greenock Country ...
4.7/5Exceptional! (299 reviews)
"We stayed at the Chambery Inn about 10 years ago and found it absolutely delightful. We were not disappointed this time around! Even with COVID precautions, our stay was wonderful."

Reviewed on Jun 23, 2021

Chambery Inn
Brook Farm Inn
3.5 out of 5
15 Hawthorne Street, Lenox, MA
The price is $159 per night from Aug 4 to Aug 4
Situated in the mountains, this bed & breakfast is within 3 mi (5 km) of The Mount, Tanglewood Music Center, and Kennedy Park. National Shrine of the Divine ...
4.5/5Wonderful! (24 reviews)
"This is a charming inn with lovely owners. They prepared a lovely picnic basket for us one night with a wonderful local wine which we took to an outdoor concert. The breakfast was very nice and the room cozy. We plan to be in Lenox again in the future, and would love to stay here again."

Reviewed on Aug 2, 2021

Brook Farm Inn
Birchwood Inn
3.5 out of 5
7 Hubbard Street, Lenox, MA
The price is $218 per night from Aug 16 to Aug 16
Situated in the suburbs, this bed & breakfast is 0.4 mi (0.7 km) from Lenox Library and 1.9 mi (3 km) from Tanglewood Music Center. Ventfort Hall Mansion and ...
4.7/5Exceptional! (69 reviews)
Exceptional
"Our stay was excellent. Tom the Innkeeper was full of information about the area. He was very welcoming and made us feel at home. The accommodations were exceptional and very clean. The breakfast for the two days we were there was 5 star. We definitely would stay there again."

Reviewed on Mar 8, 2021

Birchwood Inn
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Tanglewood Suites
2.5 out of 5
MA-102, Stockbridge, MA
The price is $219 per night from Aug 4 to Aug 4
Situated in the mountains, this bed & breakfast is within a 15-minute walk of Housatonic River and Mission House. Naumkeag and Berkshire Botanical Garden are ...
3.5/5Good! (6 reviews)
"DISASTER. The property owner called me en route to inform me that it would be cash only. The address in Expedia is incorrect and the owner called me a second time to give me a correct address that I could not find. Complete failure. I did not stay here."

Reviewed on Jun 8, 2021

Tanglewood Suites
Shaker Mill Inn
2.5 out of 5
2 Oak Street, West Stockbridge, MA
The price is $239 per night from Aug 10 to Aug 10
Situated in West Stockbridge, this bed & breakfast is within 6 mi (10 km) of Berkshire Botanical Garden, Tanglewood Music Center, and Housatonic River. Norman ...
4.8/5Exceptional! (256 reviews)
"The Inn was lovely and John, the owner, was very pleasant and quick to be sure everything was to our liking."

Reviewed on Jul 24, 2021

Shaker Mill Inn
Lakehouse Inn
4 out of 5
615 Laurel St., Lee, MA
The price is $302 per night from Aug 5 to Aug 5
Nestled on the beach, this Lee bed & breakfast is within 2 mi (3 km) of Animagic Museum of Animation, The Mount, and Lee Library. Greenock Country Club and Housatonic ...
4.8/5Exceptional! (63 reviews)
"quiet"

Reviewed on Jun 17, 2021

Lakehouse Inn
Rookwood Inn
3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
The price is $235 per night from Aug 16 to Aug 16
Situated in Lenox, this bed & breakfast is 0.1 mi (0.2 km) from Lenox Library and 1.3 mi (2.1 km) from Tanglewood Music Center. Ventfort Hall Mansion and Gilded ...
3.9/5Good! (28 reviews)
"Room too small"

Reviewed on Jul 11, 2021

Rookwood Inn
Locust Tree Bed and Breakfast LLC
3 out of 5
131 East Canaan Road, PO Box 664, Canaan, CT
The price is $105 per night from Aug 4 to Aug 4
Situated in Canaan, this bed & breakfast is 1.8 mi (2.9 km) from Land of Nod Vineyard and Winery and within 6 mi (10 km) of Ashley House and Haystack Mountain ...
4.4/5Wonderful! (193 reviews)
"We would like to compliment the owners on the lovliness of their property. We slept well, enjoyed a lovely breakfast each morning and the conversation with the guests and the owner. If anything, we would have enjoyed a chair in the room though it was a little small for an additional piece of furniture. ..."

Reviewed on Aug 2, 2021

Locust Tree Bed and Breakfast LLC
33 Main
4 out of 5
33 Main Street, Lenox, MA
The price is $379 per night from Aug 24 to Aug 24
Located in the heart of Lenox, this bed & breakfast is 0.1 mi (0.1 km) from Lenox Library and 1.4 mi (2.3 km) from Tanglewood Music Center. Ventfort Hall Mansion ...
5/5Exceptional! (40 reviews)
"We were not expecting the quality and comfort of 33 Main. Staff was very friendly, breakfast was delicious and the bedding including the pillows are now on my Annie Selke buy list. Our room, The Sunset was cozy and everything was clean and well designed. I personally loved the Nespresso coffee machine ..."

Reviewed on Jun 4, 2021

33 Main
The Inn at Stockbridge
4 out of 5
30 East Street, Stockbridge, MA
The price is $401 per night from Aug 4 to Aug 4
Situated in Stockbridge, this bed & breakfast is 1.2 mi (1.9 km) from Berkshire Theatre Festival and within 3 mi (5 km) of Housatonic River and Mission House. ...
4.8/5Exceptional! (83 reviews)
"Typical secondary large private house turned into an Inn with well preserved atmosphere. Spacious public rooms. Wonderful breakfast and friendly breakfast staff. Wine and cheese hour available early evening to relax after a busy day.Conveniently located ."

Reviewed on Jul 6, 2021

The Inn at Stockbridge
Harbour House Inn
3.5 out of 5
725 North State Road, Cheshire, MA
The price is $180 per night from Aug 18 to Aug 18
Situated in the mountains, this bed & breakfast is 1.7 mi (2.8 km) from Mount Greylock State Reservation and within 6 mi (10 km) of Topia Arts Center and East ...
4.8/5Exceptional! (20 reviews)
"Lovely, bright, airy place. Extremely welcoming and pleasant owners. Adorable room. Shared bathroom has a fantastic claw-foot bathtub. Beautiful country inn. Mass MoCa a short drive away."

Reviewed on Jul 16, 2021

Harbour House Inn
The Cornell Inn, Lenox
3 out of 5
203 Main St, Lenox, MA
The price is $225 per night from Aug 4 to Aug 4
Situated in the historical district, this bed & breakfast is 0.6 mi (1 km) from Lenox Library and 2.1 mi (3.3 km) from Tanglewood Music Center. Kennedy Park ...
4.6/5Wonderful! (304 reviews)
"From the moment we first arrived... at which time we were offered homemade ice cream as we checked in... the staff could not have been nicer. Accomodations were meant to make it feel like home and breakfast, with pancakes by Eugene, was one of the best I have ever had. Looking forward to a return ..."

Reviewed on Jul 23, 2021

The Cornell Inn, Lenox
The Windflower Inn
3 out of 5
684 South Egremont Road, Great Barrington, MA
Situated in a rural location, this bed & breakfast is 1.1 mi (1.8 km) from W.E.B. Du Bois Boyhood Homesite and 2.7 mi (4.4 km) from Jug End State Reservatio. ...
4.6/5Exceptional! (47 reviews)
"I loved staying in this 1830’s New England home. The owners were friendly and helpful. They are great folks! I would be happy to stay there again. Fresh eggs from their own hens and fresh made muffins and scones each morning—what’s not to like?!"

Reviewed on Jul 17, 2021

The Windflower Inn
Whistler's Inn Bed & Breakfast
3.5 out of 5
5 Greenwood Street, Lenox, MA
The price is $200 per night from Aug 4 to Aug 4
Situated in the mountains, this bed & breakfast is 0.4 mi (0.7 km) from Lenox Library and 1.9 mi (3 km) from Tanglewood Music Center. Ventfort Hall Mansion and ...
4/5Very Good! (224 reviews)
Stepping Back in Time
"The property allows you to step back in to the times of the "gilded age". The house is truly historic and reminded us of our trips to visit the Biltmore House. Richard, the owner, and his very lovely daughter, Lisa, were gracious hosts. Both friendly engaging and warm with a wealth of history knowledge. ..."

Reviewed on Nov 12, 2019

Whistler's Inn Bed & Breakfast
The Barrington
4 out of 5
281 Main St., Level 3, Great Barrington, MA
The price is $288 per night from Aug 4 to Aug 4
Situated near the boardwalk, this bed & breakfast is within 9 mi (15 km) of Ski Butternut, Mission House, and Chesterwood. Naumkeag and National Shrine of the ...
4.9/5Exceptional! (70 reviews)
"Delightfully welcoming"

Reviewed on Jun 15, 2021

The Barrington
The Egremont Village Inn
3 out of 5
17 Main Streeet, South Egremont, MA
Situated in South Egremont, this golf bed & breakfast is within 6 mi (10 km) of Taconic State Park, Mahaiwe Performing Arts Center, and Catamount Ski Area. Catamount ...
4.3/5Excellent! (102 reviews)
"Charming, friendly, comfortable. Good breakfast."

Reviewed on Jul 23, 2021

The Egremont Village Inn
Devonfield Inn B&B
4 out of 5
85 Stockbridge Rd., Lee, MA
The price is $329 per night from Aug 5 to Aug 5
Situated in Lee, this golf bed & breakfast is within 1 mi (2 km) of Greenock Country Club, Lee Library, and Animagic Museum of Animation. Housatonic River and ...
4.9/5Exceptional! (90 reviews)
"We felt very at home while we were at the Devonfield Inn. The breakfast was amazing!"

Reviewed on May 28, 2021

Devonfield Inn B&B
Stockbridge Country Inn
4.5 out of 5
26 Glendale Road, RR 183, Stockbridge, MA
Situated in Stockbridge, this luxury bed & breakfast is within a 15-minute walk of Housatonic River and Chesterwood. Norman Rockwell Museum and Berkshire Botanical ...
4.6/5Wonderful! (63 reviews)
"We can’t say enough good things about the Stockbridge country Inn. We loved our stay there. Far from the madding crowd but very centrally located. A little island Of calm. Delicious breakfasts and such gracious hosts. We loved our room. Comfy bed. The perfect getaway!"

Reviewed on Jul 19, 2021

Stockbridge Country Inn
Sheffield 1802 House
3.5 out of 5
48 S Main St, Sheffield, MA
Situated in Sheffield, this bed & breakfast is 0.2 mi (0.3 km) from Housatonic River and 2.2 mi (3.6 km) from Magnolia Bluffs Casino. Ashley House and Mahaiwe ...
4.5/5Wonderful! (4 reviews)
"Our first time in the Berkshires! Sheffield 1802 was a terrific place to spend the night, recover after long days hiking. Beautiful old house, perfectly maintained. Great staff, brilliant breakfasts."

Reviewed on Jul 12, 2021

Sheffield 1802 House
Eastgate Inn B&B
2.5 out of 5
207 West Street, Lenox, MA
Situated in the mountains, this bed & breakfast is within 3 mi (5 km) of Shakespeare and Company, The Mount, and Kennedy Park. Norman Rockwell Museum and Berkshire ...
4.4/5Wonderful! (42 reviews)
"We really enjoyed the Lenox area and this B&B was very convenient. I liked the room, very cozy and the bathroom was nice. She had very interesting antique decorations and a nice assortment of games. If our kids had come with us, they would have been fascinated with the place."

Reviewed on May 23, 2021

Eastgate Inn B&B
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Stockbridge

The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
The price is $212 per night from Sep 2 to Sep 2
4.3/5Excellent! (449 reviews)
"This great, big, adorable, historic hotel is exceptional and exceeded all our expectations. Worth every penny. We will be coming back soon."

Reviewed on Aug 1, 2021

The Red Lion Inn
Tanglewood Suites

Tanglewood Suites

2.5 out of 5
MA-102, Stockbridge, MA
The price is $219 per night from Aug 4 to Aug 4
3.5/5Good! (6 reviews)
"DISASTER. The property owner called me en route to inform me that it would be cash only. The address in Expedia is incorrect and the owner called me a second time to give me a correct address that I could not find. Complete failure. I did not stay here."

Reviewed on Jun 8, 2021

Tanglewood Suites
The Inn at Stockbridge

The Inn at Stockbridge

4 out of 5
30 East Street, Stockbridge, MA
The price is $401 per night from Aug 4 to Aug 4
4.8/5Exceptional! (83 reviews)
"Typical secondary large private house turned into an Inn with well preserved atmosphere. Spacious public rooms. Wonderful breakfast and friendly breakfast staff. Wine and cheese hour available early evening to relax after a busy day.Conveniently located ."

Reviewed on Jul 6, 2021

The Inn at Stockbridge
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

What is a Bed and Breakfast?

If you're looking for something a little more offbeat than your standard hotel experience, staying at a bed and breakfast in Stockbridge can be the perfect alternative for your vacation. There are 10 lodging options and 5 B&Bs in Stockbridge, making it easy to find something that meets your needs.

With attentive service, a culture suited to mingling with other guests, and of course a full breakfast to start the day, B&Bs provide a truly one-of-a-kind environment. For any museum buff, a trip to Stockbridge wouldn't be complete without a stop by Mission House or Norman Rockwell Museum.

Bed and Breakfasts in Stockbridge

Check out these top B&Bs for your stay in Stockbridge:

The Inn at Stockbridge: 4 stars, 15 rooms

  • Cooked-to-order breakfast
  • Outdoor pool

Conroy's B&B: 3.5 stars, 11 rooms

  • Buffet breakfast
  • Outdoor pool

The Cottage B&B: 3 stars, 3 rooms

1862 Seasons on Main Bed and Breakfast: 4.5 stars, 5 rooms

  • Cooked-to-order breakfast
  • Spa services

Stockbridge Country Inn: 4.5 stars, 8 rooms

  • Full breakfast
  • Outdoor pool

Weather in Stockbridge

Weather can be a big factor while planning a trip, so you can use this info to help you decide when to visit Stockbridge:

  • The hottest months are typically July and August, while January and February are the coldest months
  • Average rainfall is 45.43 inches in a year
  • January-March: Daytime temperatures average 48° F and nighttime temperatures average 11° F
  • April-June: 77° F is the daytime average and 28° F is the nighttime average
  • July-September: Daytime averages are around 79° F and nighttime averages are around 42° F
  • October-December: The average temperatures are 63° F during the day and 14° F at night

Things to See and Do in Stockbridge

Travelers enjoy Stockbridge for its bars and historic landmarks. If you'd like to see some of the area's cultural attractions, Mission House and Berkshire Theatre Festival are some worthy spots to check out during your visit.

Stockbridge is also known for its:

  • Gardens
  • Camping
  • Museums
  • Architecture
  • Monuments

What Are the Best Transportation Options in and Around Stockbridge?

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 9.5 mi (15.4 km) away from the city center. Otherwise, look for flights into Hudson, NY (HCC-Columbia County), which is 20.2 mi (32.5 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.

Frequently asked questions

More trip options