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Check prices for these dates

Next weekend
6 Mar - 8 Mar
In two weeks
13 Mar - 15 Mar
In one month
27 Mar - 29 Mar
In two months
24 Apr - 26 Apr

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, (144 reviews)
"Staff was great, very clean, Breakfast was terrific"
United States
michael
The price is HK$1,359
HK$1,518 total
includes taxes & fees
2 Mar - 3 Mar
The Trail in Adams - Berkshires’ Art Hotel
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$1,826
HK$1,931 total
includes taxes & fees
2 Mar - 3 Mar
Harbour House Inn
50-inch flat-screen TV with digital channels, Netflix, toys

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
The price is HK$1,174
HK$1,311 total
includes taxes & fees
2 Mar - 3 Mar
The Berkshire Mountain Inn
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (293 reviews)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is HK$1,025
HK$1,203 total
includes taxes & fees
14 Mar - 15 Mar
Lakehouse Inn
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (446 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
The price is HK$713
HK$783 total
includes taxes & fees
2 Mar - 3 Mar
Shaker Mill Inn
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (376 reviews)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
The price is HK$1,868
HK$2,191 total
includes taxes & fees
13 Mar - 14 Mar
The Inn at Stockbridge
Individually decorated, individually furnished, desk, laptop workspace

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (97 reviews)
"Absolutely magical at Christmas time! It was only for a quick overnight but felt like time stood still while we were there. The service was impeccable and Terry and Terri were a delight! I look forward to returning. "
United States
Jennifer
The price is HK$1,361
HK$1,521 total
includes taxes & fees
9 Mar - 10 Mar
Granville House
Living room

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (136 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Exterior

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$3,557
HK$3,973 total
includes taxes & fees
8 Mar - 9 Mar
33 Main
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, (110 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is HK$2,421
HK$2,929 total
includes taxes & fees
14 Mar - 15 Mar
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,000 reviews)
"The Inn was very nice and the staff was super friendly and attentive."
United States
Steven
The price is HK$1,044
HK$1,201 total
includes taxes & fees
2 Mar - 3 Mar
The Cornell Inn, Lenox & The Berkshires
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$1,732
HK$2,257 total
includes taxes & fees
2 Mar - 3 Mar
Experience Timeless Elegance in The Edith Wharton Room!
Lobby sitting area

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (101 reviews)
"Great property, very comfortable, incredible staff, easy access to skiing in the area!"
United States
Dominick
The price is HK$931
HK$1,043 total
includes taxes & fees
24 Mar - 25 Mar
Inn at Silver Maple Farm
3 bedrooms, bed sheets

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$1,732
HK$2,257 total
includes taxes & fees
2 Mar - 3 Mar
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
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$2,248
HK$2,928 total
includes taxes & fees
2 Mar - 3 Mar
Elegant Carriage House room with a queen bed and private patio.
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$2,377
HK$3,094 total
includes taxes & fees
2 Mar - 3 Mar
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, (27 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$3,325
HK$3,647 total
includes taxes & fees
20 Mar - 21 Mar
Inn at Kenmore Hall
Terrace/patio

Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is HK$2,506
HK$3,259 total
includes taxes & fees
2 Mar - 3 Mar
Historic Susan B. Anthony Room - Cozy & Charming Stay
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$3,087
HK$3,952 total
includes taxes & fees
22 Mar - 23 Mar
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
"Nice staff. "
Jennifer 1-night trip
Posted 9 hours ago
Comfort Inn & Suites East Greenbush - Albany

Find out more about Pittsfield

Pittsfield B&B information

Number of reviews
2,956
Accommodation
35 B&B
Lowest Price
HK$783
Highest Price
HK$3,973

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. Lakehouse Inn: 14 rooms. 8.5 mi (13.6 km) from the city centre. Enjoy the free full breakfast and snack bar/deli. Brook Farm Inn: 15 rooms. Situated 6.9 mi (11.1 km) from the heart of Pittsfield. Enjoy the free cooked breakfast and outdoor pool. Shaker Mill Inn: 9 rooms. 9.8 mi (15.8 km) from the city centre. Chambery Inn: 9 rooms. Located 9.7 mi (15.5 km) from the core of Pittsfield. Enjoy the private garden and snack bar/deli.
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 Bousquet Ski Area and Hancock Shaker Village 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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