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Check prices for these dates

Next weekend
3 Apr - 5 Apr
In two weeks
10 Apr - 12 Apr
In one month
24 Apr - 26 Apr
In two months
22 May - 24 May

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, (145 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 AED 638
AED 713 total
includes taxes & fees
26 Mar - 27 Mar
The Trail in Adams - Berkshires’ Art Hotel
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (295 reviews)
"Friendly staff, great location, beautiful views, cozy room."
United States
Elizabeth
The price is AED 497
AED 583 total
includes taxes & fees
27 Mar - 28 Mar
Lakehouse Inn
Double Room | Individually decorated, iron/ironing board, free WiFi

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
The price is AED 551
AED 615 total
includes taxes & fees
26 Mar - 27 Mar
The Berkshire Mountain 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
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 AED 932
AED 985 total
includes taxes & fees
26 Mar - 27 Mar
Harbour House 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 AED 372
AED 408 total
includes taxes & fees
30 Mar - 31 Mar
Shaker Mill 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 AED 877
AED 1,029 total
includes taxes & fees
27 Mar - 28 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)
"Everything about Granville House is delightful. The owners have paid attention to every detail, from the decor and the way the rooms are appointed to the comfortable bed and the delicious hot breakfast."
United States
Ann
The price is AED 639
AED 714 total
includes taxes & fees
26 Mar - 27 Mar
Granville House
Room #10 Queen's Cottage | Living room | Flat-screen TV

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 AED 1,208
AED 1,350 total
includes taxes & fees
26 Mar - 27 Mar
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 AED 1,651
AED 1,844 total
includes taxes & fees
2 Apr - 3 Apr
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 813
AED 1,064 total
includes taxes & fees
27 Mar - 28 Mar
Experience Timeless Elegance in The Edith Wharton Room!
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, (110 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is AED 1,137
AED 1,375 total
includes taxes & fees
8 Apr - 9 Apr
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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 AED 437
AED 490 total
includes taxes & fees
26 Mar - 27 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 AED 813
AED 1,060 total
includes taxes & fees
26 Mar - 27 Mar
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
9.0 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 AED 475
AED 546 total
includes taxes & fees
27 Mar - 28 Mar
The Cornell Inn, Lenox & The Berkshires
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 934
AED 1,195 total
includes taxes & fees
3 Apr - 4 Apr
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 AED 995
AED 1,272 total
includes taxes & fees
3 Apr - 4 Apr
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 AED 2,112
AED 2,317 total
includes taxes & fees
29 Mar - 30 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 AED 1,055
AED 1,346 total
includes taxes & fees
3 Apr - 4 Apr
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 AED 1,328
AED 1,737 total
includes taxes & fees
3 Apr - 4 Apr
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

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

8/10 Good
"Staff was very accommodating. Room was ok but toilet didn’t flush without the water constantly running. Shower gel, shampoo & condition bottles were all empty in the shower. Had to call for new ones. "
Timothy F 5-night trip
Posted 15 hours ago
Best Western Plus Berkshire Hills Inn & Suites

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. Lakehouse Inn: 14 rooms. 8.5 mi (13.6 km) from the downtown core. Enjoy the free full breakfast and deli. Shaker Mill Inn: 9 rooms. Situated 9.8 mi (15.8 km) from the heart of Pittsfield. 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 tubs.
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 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?
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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