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12 Sep - 14 Sep
In two weeks
19 Sep - 21 Sep
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3 Oct - 5 Oct
In two months
31 Oct - 2 Nov

B&B in Pittsfield

Our top choices for Pittsfield bed & breakfast

The Trail in Adams - Berkshires’ Art Hotel
Terrace/patio

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
8.8 out of 10, Excellent, (135)
"We had an excellent experience. The location was convenient for our needs, clean, and tastefully done. It's excellent value for the area. It must be said that a younger traveller will probably be more comfortable with the low-touch approach (text check in, code-locked doors), but they've clearly made an effort to be more accessible to a traveler looking for something more traditional. "
The price is AED 657
AED 733 total
includes taxes & fees
8 Sep - 9 Sep
The Trail in Adams - Berkshires’ Art Hotel
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (51)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
The price is AED 944
AED 998 total
includes taxes & fees
9 Sep - 10 Sep
Harbour House Inn
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (369)
"ease of late check in. Super comfortable room."
Chambery Inn
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1003)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is AED 469
AED 667 total
includes taxes & fees
4 Sep - 5 Sep
The Cornell Inn, Lenox & The Berkshires
The Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
The price is AED 1,641
AED 1,924 total
includes taxes & fees
4 Sep - 5 Sep
The Inn at Stockbridge
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (486)
"Nice quaint out of the ordinary vacation experience. "
The price is AED 592
AED 661 total
includes taxes & fees
3 Sep - 4 Sep
Whistler's Inn Bed & Breakfast
Brook Farm Inn
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (160)
"Inn was gorgeous and staff exceptional!"
Brook Farm Inn
Experience Timeless Elegance in The Edith Wharton Room!
1 bedroom, bed sheets, wheelchair access

Experience Timeless Elegance in The Edith Wharton Room!

The price is AED 762
AED 1,118 total
includes taxes & fees
4 Sep - 5 Sep
Experience Timeless Elegance in The Edith Wharton Room!
33 Main
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

33 Main

4.0 star property
10.0 out of 10, Exceptional, (71)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
The price is AED 2,069
AED 2,311 total
includes taxes & fees
18 Sep - 19 Sep
33 Main
Tanglewood Suites
2 Bedrooms 1 Bath | 1 bedroom, premium bedding, iron/ironing board, free WiFi

Tanglewood Suites

2.5 star property
6.8 out of 10, (20)
"The owner did not honor our confirmed Expedia reservation, so we had to find a hotel at the last minute. She made up various excuses and was very rude."
The price is AED 988
AED 988 total
includes taxes & fees
3 Sep - 4 Sep
Tanglewood Suites
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
3 bedrooms, bed sheets

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

The price is AED 762
AED 1,118 total
includes taxes & fees
4 Sep - 5 Sep
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Elegant Carriage House room with a queen bed and private patio.
1 bedroom, WiFi, bed sheets

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

The price is AED 821
AED 1,183 total
includes taxes & fees
10 Sep - 11 Sep
Elegant Carriage House room with a queen bed and private patio.
Cozy Carriage House room with a double bed and private balcony
1 bedroom, bed sheets

Cozy Carriage House room with a double bed and private balcony

The price is AED 879
AED 1,265 total
includes taxes & fees
4 Sep - 5 Sep
Cozy Carriage House room with a double bed and private balcony
Historic Susan B. Anthony Room - Cozy & Charming Stay
Terrace/patio

Historic Susan B. Anthony Room - Cozy & Charming Stay

The price is AED 938
AED 1,343 total
includes taxes & fees
3 Sep - 4 Sep
Historic Susan B. Anthony Room - Cozy & Charming Stay
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Fireplace

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

The price is AED 1,203
AED 1,655 total
includes taxes & fees
4 Sep - 5 Sep
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
1 bedroom, bed sheets

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

The price is AED 1,320
AED 1,803 total
includes taxes & fees
7 Sep - 8 Sep
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Fireplace

Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

The price is AED 1,496
AED 2,020 total
includes taxes & fees
7 Sep - 8 Sep
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Elegant suite with a king bed, fireplace, and kitchenette.
Living area

Elegant suite with a king bed, fireplace, and kitchenette.

The price is AED 1,496
AED 2,024 total
includes taxes & fees
3 Sep - 4 Sep
Elegant suite with a king bed, fireplace, and kitchenette.
Granville House
Individually decorated, individually furnished, desk, laptop workspace

Granville House

3.0 star property
10.0 out of 10, Exceptional, (84)
"Phenomenal hospitality, eclectic decor, luxurious sleep - we have been raving about our stay and will definitely be back!"
The price is AED 915
AED 1,022 total
includes taxes & fees
8 Sep - 9 Sep
Granville House
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Room was very clean. There is a lot to do at the property, 2 pools, activities for the kids. Lots of things to do in the area "
Judy 2-night trip
Posted 5 days ago
Vacation Village in the Berkshires

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. Inn at Silver Maple Farm: 11 rooms. 10.9 mi (17.5 km) from the downtown core. Enjoy the free buffet breakfast and designer toiletries. Shaker Mill Inn: 9 rooms. Situated 9.8 mi (15.8 km) from the heart of Pittsfield. Tanglewood Suites: 2 rooms. 11.6 mi (18.6 km) from the heart of downtown.Chambery Inn: 9 rooms. Located 9.7 mi (15.5 km) from the core of Pittsfield. Enjoy the private yard and deli.
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 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?
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.