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Check prices for these dates

Next weekend
3 Jul - 5 Jul
In two weeks
10 Jul - 12 Jul
In one month
24 Jul - 26 Jul
In two months
21 Aug - 23 Aug

Our top choices for Pittsfield bed & breakfast

Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (462 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is AED 547
AED 600 total
includes taxes & fees
23 Jun - 24 Jun
Shaker Mill Inn
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 AED 725
AED 810 total
includes taxes & fees
29 Jun - 30 Jun
The Trail in Adams - Berkshires’ Art Hotel
Aerial view

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (108 reviews)
"Very nice hotel."
United States
Erdem
The price is AED 584
AED 654 total
includes taxes & fees
23 Jun - 24 Jun
Inn at Silver Maple Farm
Exterior

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
8.8 out of 10, Excellent, (8 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 AED 908
AED 1,014 total
includes taxes & fees
24 Jun - 25 Jun
The Berkshire Mountain Inn
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
"Great place, nice amenities and convenient location, highly recommended."
United States
Arthur
The price is AED 716
AED 824 total
includes taxes & fees
29 Jun - 30 Jun
The Cornell Inn, Lenox & The Berkshires
Individually decorated, individually furnished, desk, laptop workspace

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (102 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 AED 1,010
AED 1,128 total
includes taxes & fees
23 Jun - 24 Jun
Granville House
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (379 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 AED 992
AED 1,108 total
includes taxes & fees
29 Jun - 30 Jun
Chambery Inn
Suite, Private Bathroom (RedBird Suite) | 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 AED 1,213
AED 1,467 total
includes taxes & fees
6 Jul - 7 Jul
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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 AED 734
AED 820 total
includes taxes & fees
23 Jun - 24 Jun
Whistler's Inn Bed & Breakfast
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Great spot close to town. Cozy, tasteful, comfortable room. Nice breakfasts and pleasant interaction with the staff. We love the Berkshires and we’ll definitely stay here again."
United States
Stephen
The price is AED 1,327
AED 1,556 total
includes taxes & fees
23 Jun - 24 Jun
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, (138 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is AED 1,429
AED 1,596 total
includes taxes & fees
24 Jun - 25 Jun
Devonfield Inn B&B
Luxury Room, 1 King Bed, Bathtub | 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 AED 2,119
AED 2,367 total
includes taxes & fees
23 Jun - 24 Jun
33 Main
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 AED 1,203
AED 1,572 total
includes taxes & fees
29 Jun - 30 Jun
Experience Timeless Elegance in The Edith Wharton Room!
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 AED 1,203
AED 1,572 total
includes taxes & fees
29 Jun - 30 Jun
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Front of property

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (167 reviews)
"Lovely stay!"
United States
Jiacheng
The price is AED 694
AED 805 total
includes taxes & fees
23 Jun - 24 Jun
Brook Farm Inn
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 AED 1,408
AED 1,841 total
includes taxes & fees
6 Jul - 7 Jul
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 AED 1,261
AED 1,640 total
includes taxes & fees
23 Jun - 24 Jun
Historic Susan B. Anthony Room - Cozy & Charming Stay
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 AED 1,320
AED 1,715 total
includes taxes & fees
29 Jun - 30 Jun
Cozy Carriage House room with a double bed and private balcony
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 AED 1,643
AED 2,147 total
includes taxes & fees
29 Jun - 30 Jun
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Shower, towels

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is AED 1,643
AED 2,086 total
includes taxes & fees
23 Jun - 24 Jun
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
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

The Red Lion Inn

The Red Lion Inn

8/10 Good
"I did not stay in the main building but had a room in a separate building on the same block. I quite liked my room away from the inn. It was roomy, quiet, across the street from a church, easy walk to the cafe, and there was a bunny 🐰 eating grass outside each night. I think I will request such a room away from the hubbub when I return. The food at the Red Lion's Inn's 'Widow's' tavern was delicious. Just know the buildings are indeed OLD so if you are seeking great water pressure or modern vibe, this is not your place. Love the history of this place!"
Tina 5-night trip
Posted 2 hours ago
The Red Lion Inn

Frequently asked questions

Searching for B&Bs in Pittsfield?
If you're looking for something a little more offbeat than your standard hotel, a stay at a bed and breakfast might be the perfect option for your vacation. 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 right choice for your stay?
With attentive service, opportunities to meet guests from other places, and delectable breakfasts, B&Bs provide a unique setting.
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 décor. Shaker Mill Inn: 9 rooms. 9.8 mi (15.8 km) from the downtown core. Chambery Inn: 9 rooms. Situated 9.7 mi (15.5 km) from the heart of Pittsfield. Enjoy the private yard and deli. The Trail in Adams - Berkshires' Art Hotel: 9 rooms. 13.8 mi (22.2 km) from the heart of downtown. Enjoy the unique décor and patio area.
When should I stay at a B&B in Pittsfield?
When you're dreaming of a getaway to Pittsfield, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Pittsfield are January, March, February, and November, with each month seeing an average of 7 inches 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 check out. You might put Berkshire Athenaeum and Barrington Stage Company on your list if you want to see more of the area.
How can I get to and around Pittsfield?
Planning your excursions in and around Pittsfield is easier with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 2.5 mi (4 km) from the city center. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 25.7 mi (41.4 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.

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