Search B&B in Pittsfield

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Front of property – evening/night
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (106)
"The classic character of the Inn is so beautiful and adds to the whole experience!"
The price is HK$2,099
HK$2,345 total
includes taxes & fees
28 May - 29 May
Devonfield Inn B&B
Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main
4.0 star property
10.0 out of 10, Exceptional, (62)
"I love the fact that it only had eight rooms they had happy hour from 5 to 6 PM so we are able to meet other people at the hotel. I love the rooms and the cleanliness and especially the breakfast they were amazing and delicious!! I would recommend this hotel highly!"
The price is HK$3,018
HK$3,371 total
includes taxes & fees
29 May - 30 May
33 Main
Interior detail
Granville House
4.0 star property
10.0 out of 10, Exceptional, (70)
"Very nice hosts and lovely and inventive decor."
The price is HK$1,560
HK$1,742 total
includes taxes & fees
23 May - 24 May
Granville House
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Lobby
Inn at Kenmore Hall
3.0 star property
10.0 out of 10, Exceptional, (25)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
Inn at Kenmore Hall
1 bedroom, desk, iron/ironing board, WiFi
Romantic Boutique Hotel / B&B - Deluxe Firespa Suite
10.0 out of 10, Exceptional, (4)
"The property was a converted parochial school The rooms were old class rooms. Very spacious and extremely comfortable. Lots to do in the area or like we did just relax . We would recommend the inn for a great summer getaway . Community theater is a big attraction although not open yet Enjoy"
The price is HK$3,112
HK$3,955 total
includes taxes & fees
23 May - 24 May
Romantic Boutique Hotel / B&B - Deluxe Firespa Suite
1 bedroom, desk, iron/ironing board, WiFi
Romantic Boutique Hotel / Bed and Breakfast - Deluxe Schoolhouse Suite
10.0 out of 10, Exceptional, (6)
The price is HK$3,112
HK$3,955 total
includes taxes & fees
23 May - 24 May
Romantic Boutique Hotel / Bed and Breakfast - Deluxe Schoolhouse Suite
Interior
The Red Door B&B
3.0 star property
10.0 out of 10, Exceptional, (5)
"We loved staying at this b&b. The owners were very accommodating, kind and helpful. Because of the pandemic, they only took us for the weekend. The breakfasts were above and beyond our expectations, simply fantastic. We highly recommend this beautiful place and we will be back for sure. "
The Red Door B&B
Aerial view
Inn at Silver Maple Farm
3.0 star property
9.8 out of 10, Exceptional, (68)
"I had a wonderful stay here with my sister. I would definitely go back next time i am in the area"
The price is HK$1,163
HK$1,256 total
includes taxes & fees
23 May - 24 May
Inn at Silver Maple Farm
Exterior
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
9.8 out of 10, Exceptional, (10)
"We would return to the inn again. Bob was wonderful and very, very accommodating:-)"
The price is HK$2,332
HK$2,910 total
includes taxes & fees
27 May - 28 May
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
Aerial view
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, (152)
"The Lakehouse Inn is really cute, right on a lake with wonderful waterfront spaces. The bathroom situation is more European--toilet and shower in the bathroom, sink outside. There was no tub, not a problem for me but good to be aware of. The morning breakfast was delicious! I was greeted with a white wine sangria. It's conveniently located for roaming around Stockbridge, Great Barrington, etc. Close to the Norman Rockwell museum, Hancock Shaker Village, Edith Wharton estate. Would absolutely...
The price is HK$1,053
HK$1,235 total
includes taxes & fees
28 May - 29 May
Lakehouse Inn
Garden
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (383)
"We felt like the place was all our own. From the en suite breakfast to our private deck, we felt right at home immediately and had a lovely weekend stay. The surrounding mountains and quaint New England mill town were off-the-charts charming. Our inn keepers were just a phone call away when we had a request. Everything was immaculately clean and extremely well maintained (I'm a handyman at heart). I can't wait for you to stay here- it's minutes away from Stockbridge, Lennox, Great...
The price is HK$1,069
HK$1,173 total
includes taxes & fees
30 May - 31 May
Shaker Mill Inn
Exterior
The Inn at Stockbridge
4.0 star property
9.6 out of 10, Exceptional, (92)
"Great B&B with everything you need especially for a quick getaway to vist Stockbridge & Great Barrington Massachusetts. The new owners have added new touches to this Inn and the pride of ownership shows. Highly recommended 👌 "
The Inn at Stockbridge
Front of property
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (356)
"Amazing place.."
The price is HK$1,867
HK$2,085 total
includes taxes & fees
28 May - 29 May
Chambery Inn
Premium bedding, individually decorated, desk, iron/ironing board
The Barrington
4.0 star property
9.6 out of 10, Exceptional, (98)
"As always, our stay at The Barrington was wonderful. The rooms are large, lovely and the bed comfortable. The service is great and everyone is so friendly and accommodating! The breakfast is delicious. We truly enjoy our stay, every time!"
The price is HK$2,535
HK$2,831 total
includes taxes & fees
27 May - 28 May
The Barrington
1 bedroom, desk, WiFi, bed sheets
Romantic Boutique Hotel / Bed and Breakfast - SchoolHouse Suite
9.6 out of 10, Exceptional, (8)
The price is HK$3,112
HK$3,955 total
includes taxes & fees
23 May - 24 May
Romantic Boutique Hotel / Bed and Breakfast - SchoolHouse Suite
Front of property
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (135)
"This is a charming and very pleasant place to stay."
The price is HK$1,108
HK$1,237 total
includes taxes & fees
23 May - 24 May
Brook Farm Inn
Exterior
Harbour House Inn
3.5 star property
9.4 out of 10, Exceptional, (48)
"Decorations were beautiful, room and bed were so comfortable, hostess and food were wonderful. Brandi was thoughtful in every way possible. Can't go wrong choosing this place over a chain. Love it!"
The price is HK$1,928
HK$2,038 total
includes taxes & fees
30 May - 31 May
Harbour House Inn
View from property
Berkshire Mountain House
3.0 star property
9.4 out of 10, Exceptional, (22)
"GORGEOUS Scenery and NICE place to stay !"
Berkshire Mountain House
Business centre
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
9.2 out of 10, Wonderful, (101)
"The b&b was so beautiful and unique! The area was serene. The host was very sweet and accommodating."
The price is HK$2,941
HK$3,558 total
includes taxes & fees
23 May - 24 May
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Porch
Eastgate Inn B&B
2.5 star property
9.0 out of 10, Wonderful, (64)
"The owner, Daliya, is very friendly and helpful, with good advice. We enjoyed the breakfasts."
Eastgate Inn B&B
Don't see what you're looking for?
See all available properties in Pittsfield
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 Pittsfield

Interior
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Interior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (184)
"My husband and I had a very peaceful and relaxing long weekend at this lake house! It was very clean and has everything you need. We spent the majority of our time on the wonderful screened-in porch. The location was great and there was a little store/restaurant only a couple minutes walk up the street that was convenient and the food was really good! Overall, a great place to stay!"
Peace and quiet on the lake
Property grounds
Chic Pittsfield Home With A View!
9.0 out of 10, Wonderful, (4)
"Nicely decorated and clean. It had everything we needed, including kitchen supplies and detergent for the washer/dryer. Great rental for our family getaway."
Chic Pittsfield Home With A View!
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.

Pittsfield B&B information

Number of reviews
2,475
Accommodation
30 B&B
Lowest Price
HK$951
Highest Price
HK$3,112

Frequently asked questions

Searching for B&Bs in Pittsfield?
If you’re hoping for something a little more offbeat than your standard hotel, a bed and breakfast could be a great option for your trip. While you’re here, you can get to know Pittsfield by exploring its natural beauty—consider stopping at Pittsfield State Forest and Canoe Meadows Wildlife Sanctuary.
How do you know if a B&B is the best choice for your stay?
With attentive service, opportunities to interact with the owner and tasty breakfasts, B&Bs offer a one-of-a-kind environment.
What are the best B&Bs in Pittsfield?
Here are some well-liked B&Bs in the surrounding area: The Cornell Inn, Lenox: 5.9 mi (9.4 km) from the heart of Pittsfield. Enjoy the free full breakfast and unique decor. Lakehouse Inn: 14 rooms. 8.5 mi (13.6 km) from the city centre. Enjoy the free full breakfast and snack bar/deli. Shaker Mill Inn: 9 rooms. Situated 9.8 mi (15.8 km) from the heart of Pittsfield. Inn at Silver Maple Farm: 11 rooms. 10.9 mi (17.5 km) from the city centre. Enjoy the free buffet breakfast and designer toiletries. Devonfield Inn B&B: 11 rooms. Located 10.2 mi (16.4 km) from the core of Pittsfield. Enjoy the free full breakfast and Jetted bath.
When is the best time to stay at a B&B in Pittsfield?
When you’re dreaming of a trip to Pittsfield, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Pittsfield are January, March, February and November, with each month seeing an average of 18 cm of snowfall.
What is there to do in Pittsfield?
When you want to explore some cultural attractions on your trip, Berkshire Museum and Colonial Theater are worthy sites to visit. You should put Barrington Stage Company and Bousquet Ski Area on your list if you want to see more of the area.
How can I get to and around Pittsfield?
You can plan your excursions in and around Pittsfield ahead of time with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 2.5 mi (4 km) from the heart of the city. Otherwise, look for flights into Hudson, NY (HCC-Columbia County), which is 25.7 mi (41.4 km) away. If you’d like to explore around the area, you may want to rent a car for your trip.

Recent Hotel Reviews in Pittsfield
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