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Check prices for these dates

Next weekend
24 Apr - 26 Apr
In two weeks
1 May - 3 May
In one month
15 May - 17 May
In two months
12 Jun - 14 Jun

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
8.8 out of 10, Excellent, (146 reviews)
"Great little Inn with a well equipped kitchen, clean rooms, and art books. It made for a lovely base for our two day Berkshires adventure."
United States
selmin
The price is HK$1,361
HK$1,520 total
includes taxes & fees
16 Apr - 17 Apr
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$1,987
HK$2,100 total
includes taxes & fees
27 Apr - 28 Apr
Harbour House Inn
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (376 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$1,339
HK$1,496 total
includes taxes & fees
21 Apr - 22 Apr
Chambery Inn
Individually decorated, iron/ironing board, free WiFi

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
9.6 out of 10, Exceptional, (5 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$1,566
HK$1,749 total
includes taxes & fees
16 Apr - 17 Apr
The Berkshire Mountain Inn
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (447 reviews)
"Everything was great— the cleanliness, the plentiful breakfast, the character and coziness, and the proximity to Amici across the street (free dessert with your room key)."
United States
Patrick
The price is HK$850
HK$933 total
includes taxes & fees
23 Apr - 24 Apr
Shaker Mill Inn
Individually decorated, individually furnished, desk, laptop workspace

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (99 reviews)
"Very cosy and friendly "
United States
Dominic
The price is HK$1,755
HK$1,960 total
includes taxes & fees
16 Apr - 17 Apr
Granville House
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$1,777
HK$2,084 total
includes taxes & fees
17 Apr - 18 Apr
The Inn at Stockbridge
Front of property – evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (137 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
The price is HK$2,342
HK$2,615 total
includes taxes & fees
27 Apr - 28 Apr
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$1,840
HK$2,055 total
includes taxes & fees
3 May - 4 May
Whistler's Inn Bed & Breakfast
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$3,366
HK$3,759 total
includes taxes & fees
23 Apr - 24 Apr
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$2,424
HK$2,933 total
includes taxes & fees
29 Apr - 30 Apr
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
9.2 out of 10, Wonderful, (1,000 reviews)
"Beautiful Inn, hosts are most welcome and the breakfast was perfect. Heading back for certain!"
United States
Karen
The price is HK$1,012
HK$1,165 total
includes taxes & fees
12 May - 13 May
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$1,687
HK$2,206 total
includes taxes & fees
6 May - 7 May
Experience Timeless Elegance in The Edith Wharton Room!
Aerial view

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (103 reviews)
"Great property, very comfortable, incredible staff, easy access to skiing in the area!"
United States
Dominick
The price is HK$1,089
HK$1,219 total
includes taxes & fees
26 Apr - 27 Apr
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$1,687
HK$2,180 total
includes taxes & fees
10 May - 11 May
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
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$3,329
HK$3,652 total
includes taxes & fees
10 May - 11 May
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$2,063
HK$2,672 total
includes taxes & fees
6 May - 7 May
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$2,188
HK$2,851 total
includes taxes & fees
7 May - 8 May
Cozy Carriage House room with a double bed and private balcony
Terrace/patio

Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is HK$2,313
HK$2,968 total
includes taxes & fees
10 May - 11 May
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$2,877
HK$3,737 total
includes taxes & fees
3 May - 4 May
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"Clean, hot shower. Great pressure"
Tammy 6-night trip
Posted 8 hours ago
Berkshire Mountain Lodge

Find out more about Pittsfield

Pittsfield B&B information

Number of reviews
2,229
Accommodation
35 B&B
Lowest Price
HK$933
Highest Price
HK$3,759

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. Shaker Mill Inn: 9 rooms. 9.8 mi (15.8 km) from the city centre. The Trail in Adams - Berkshires' Art Hotel: 9 rooms. Located 13.8 mi (22.2 km) from the core of Pittsfield. Enjoy the unique decor and arcade/games room.
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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