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Check prices for these dates

Next weekend
5 Jun - 7 Jun
In two weeks
12 Jun - 14 Jun
In one month
26 Jun - 28 Jun
In two months
24 Jul - 26 Jul

Our top choices for Pittsfield bed & breakfast

Terrace/patio

The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.0 out of 10, Wonderful, (151 reviews)
"Incredible staff, free parking and cute rooms!"
Canada
Priscilla
The price is HK$1,430
HK$1,598 total
includes taxes & fees
1 Jun - 2 Jun
The Trail in Adams - Berkshires’ Art Hotel
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (377 reviews)
"Yes the room was spotless and always the staff is ready to answer any questions that we might have. We have been enjoying the Chambery Inn for many years always had a great stay and again looking for our next visit. Vincent Farricielli and Roibert Modena. "
United States
robert
The price is HK$1,340
HK$1,497 total
includes taxes & fees
7 Jun - 8 Jun
Chambery Inn
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (457 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is HK$1,168
HK$1,281 total
includes taxes & fees
1 Jun - 2 Jun
Shaker Mill Inn
Exterior

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is HK$1,988
HK$2,101 total
includes taxes & fees
1 Jun - 2 Jun
Harbour House Inn
Exterior

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
9.8 out of 10, Exceptional, (6 reviews)
"The new owners have done a great job. The place is immaculate, the room was very comfortable and well appointed, the common areas charming. Highly recommended."
United States
Robert
The price is HK$1,938
HK$2,164 total
includes taxes & fees
1 Jun - 2 Jun
The Berkshire Mountain Inn
Individually decorated, individually furnished, desk, laptop workspace

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (101 reviews)
"Beautiful home with warm and friendly hosts. The rooms were tastefully designed, the bed was very comfortable and the large bathroom was luxurious. The breakfast was absolutely delicious. We will definitely stay again next time we are in Great Barrington. "
United States
Nicole
The price is HK$1,567
HK$1,751 total
includes taxes & fees
1 Jun - 2 Jun
Granville House
Front of property – evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (138 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is HK$2,578
HK$2,880 total
includes taxes & fees
3 Jun - 4 Jun
Devonfield Inn B&B
Property grounds

Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (501 reviews)
"This family owned Inn is absolutely charming and the owners are so nice! I will definitely stay here again when I visit the Berkshires."
United States
Stacey
The price is HK$2,088
HK$2,333 total
includes taxes & fees
16 Jun - 17 Jun
Whistler's Inn Bed & Breakfast
View from room

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (111 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is HK$2,587
HK$3,130 total
includes taxes & fees
15 Jun - 16 Jun
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
1 bedroom, WiFi, bed sheets, wheelchair access

Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is HK$2,064
HK$2,700 total
includes taxes & fees
1 Jun - 2 Jun
Experience Timeless Elegance in The Edith Wharton Room!
Premium bedding, individually decorated, iron/ironing board, free WiFi

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is HK$4,892
HK$5,464 total
includes taxes & fees
1 Jun - 2 Jun
33 Main
Aerial view

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (107 reviews)
"Very nice hotel."
United States
Erdem
The price is HK$1,246
HK$1,396 total
includes taxes & fees
4 Jun - 5 Jun
Inn at Silver Maple Farm
Shower, towels

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is HK$1,939
HK$2,539 total
includes taxes & fees
3 Jun - 4 Jun
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Great place, nice amenities and convenient location, highly recommended."
United States
Arthur
The price is HK$1,220
HK$1,404 total
includes taxes & fees
7 Jun - 8 Jun
The Cornell Inn, Lenox & The Berkshires
Interior

Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony
Lenox
The price is HK$2,566
HK$3,345 total
includes taxes & fees
1 Jun - 2 Jun
Cozy Carriage House room with a double bed and private balcony
Lobby

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
Richmond
10.0 out of 10, Exceptional, (28 reviews)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is HK$3,331
HK$3,654 total
includes taxes & fees
16 Jun - 17 Jun
Inn at Kenmore Hall
Interior

Elegant Carriage House room with a queen bed and private patio.

Elegant Carriage House room with a queen bed and private patio.
Lenox
The price is HK$2,440
HK$3,175 total
includes taxes & fees
14 Jun - 15 Jun
Elegant Carriage House room with a queen bed and private patio.
Terrace/patio

Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is HK$2,691
HK$3,507 total
includes taxes & fees
1 Jun - 2 Jun
Historic Susan B. Anthony Room - Cozy & Charming Stay
Shower, towels

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is HK$3,506
HK$4,459 total
includes taxes & fees
1 Jun - 2 Jun
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
1 bedroom, bed sheets

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Lenox
The price is HK$3,255
HK$4,250 total
includes taxes & fees
1 Jun - 2 Jun
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
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.
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Top Pittsfield Hotel Reviews

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"Great friendly hotel with great lobby, hot breakfast, spacious individual working place at the tables. 24/7 hot and drinking water. The only drawback is that the window is theoretically opennable by construction but the hotel installed the obstacle to open the window. Thus, we could not enjoy fresh night air."
Pavel 2-night trip
Posted less than an hour ago
Comfort Inn & Suites East Greenbush - Albany

Find out more about Pittsfield

Pittsfield B&B information

Number of reviews
2,465
Accommodation
35 B&B
Lowest Price
HK$1,281
Highest Price
HK$5,464

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. If you want to lose yourself exploring fascinating exhibits, you might consider stopping by Berkshire Museum and Hancock Shaker Village while you're in town.
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 & The Berkshires: 5.9 mi (9.4 km) from the heart of Pittsfield. Enjoy the free full breakfast and unique decor. Shaker Mill Inn: 9 rooms. 9.8 mi (15.8 km) from the city centre. Chambery Inn: 9 rooms. 9.7 mi (15.5 km) from the city centre. Enjoy the private garden and snack bar/deli. Inn at Silver Maple Farm: 11 rooms. Located 10.9 mi (17.5 km) from the core of Pittsfield. Enjoy the free buffet breakfast and designer toiletries.
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.

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