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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

Compare 24 B&B in Pittsfield with updated reviews, rates, and availability.

The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.0 star property
8.8 out of 10, Excellent, (1053)
"What a beautiful, well-appointed room we stayed in at the Cornell! We had "Jennifer's Room" and loved the decor and comfort of the space, including fireplace!! The breakfast was delicious and the staff was super friendly. We'll definitely be back!! "
The price is AED 357
AED 543 total
includes taxes & fees
11 Apr - 12 Apr
The Cornell Inn, Lenox & The Berkshires
Lakehouse Inn
Aerial view

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (252)
"Wonderful Location"
Lakehouse Inn
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (408)
"Beautiful room, very clean. breakfast was not what i was expecting, walk way from parking lot covered with ice and snow, very dangerous to walk, needs to be cleaned or at least put some salt on the ground. other then that everything was excellent. will stay again"
The price is AED 533
AED 584 total
includes taxes & fees
30 Mar - 31 Mar
Shaker Mill Inn
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (363)
"Chamberry Inn was a nice, quiet, relaxing stay. Enjoyed every second of it. The staff were kind and helpful. Would definitely stay again if I was in the area."
The price is AED 881
AED 985 total
includes taxes & fees
29 Mar - 30 Mar
Chambery Inn
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, (128)
"The Trail in Adams offered me exactly what I needed: a quiet and convenient place prepare for a day in the woods the next day. Very convenient walking to nearby restaurants, right in the middle of Adams. There was a snowstorm that night, and the walks were shoveled several times that evening and the next morning. "
The price is AED 638
AED 713 total
includes taxes & fees
3 Apr - 4 Apr
The Trail in Adams - Berkshires’ Art Hotel
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, (70)
"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 1,441
AED 1,610 total
includes taxes & fees
30 Mar - 31 Mar
33 Main
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (151)
"Loves that they had en EV charger for me to charge while we were “home”. Beautiful location and house. Welcoming hospitality that was very refreshing. Thank you. "
The price is AED 724
AED 809 total
includes taxes & fees
29 Mar - 30 Mar
Brook Farm Inn
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (122)
"Beautiful property, great service "
The price is AED 915
AED 1,022 total
includes taxes & fees
30 Mar - 31 Mar
Devonfield Inn B&B
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (471)
"I liked that it is an older style bed and breakfast place. You could say "classy" or "vintage". It reminded me of places where I would visit with family when I was a child. I received a personal welcome and orientation to the property. Breakfast was nice and cooked options were available for me to choose. Another guest in the dining room at breakfast was also enjoying the visit and it was natural to strike up a conversation and get to know each other. It was a more personal kind of stay than...
Whistler's Inn Bed & Breakfast
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business center

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
9.2 out of 10, Wonderful, (105)
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer most questions"
The price is AED 1,559
AED 1,885 total
includes taxes & fees
2 Apr - 3 Apr
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Inn at Silver Maple Farm
Aerial view

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (81)
"Everything "
The price is AED 584
AED 631 total
includes taxes & fees
30 Mar - 31 Mar
Inn at Silver Maple Farm
The Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"We we were in the Out of Africa room, set apart in a complex of 4 suites in a unit apart from the Inn itself. The room was uniquely created to feel like an escape to Africa, and heated by a lovely gas fireplace. The breakfast both mornings, delicious. A perfect getaway!"
The Inn at Stockbridge
Granville House
Interior detail

Granville House

3.0 star property
10.0 out of 10, Exceptional, (82)
"Phenomenal hospitality, eclectic decor, luxurious sleep - we have been raving about our stay and will definitely be back!"
The price is AED 826
AED 923 total
includes taxes & fees
30 Mar - 31 Mar
Granville House
Tanglewood Suites
2 Bedrooms 1 Bath | Premium bedding, iron/ironing board, free WiFi, bed sheets

Tanglewood Suites

2.5 star property
8.0 out of 10, Very Good, (15)
"Portion of hosts home, separate and available for rent. Heating system not efficient and took some work to sort out how to keep all areas of the unit comfortably heated. Beds clean and comfortable. Overall cleanliness was good. Bath facilities are an addition to existing structure and sufficient, but could use some TLC. Host is eager to please and pleasant to interact with. Listing indicates free breakfast for all guests. However, upon arrival, we were advised there is no winter offering of...
The price is AED 804
AED 804 total
includes taxes & fees
29 Mar - 30 Mar
Tanglewood Suites
Inn at Kenmore Hall
Lobby

Inn at Kenmore Hall

3.0 star property
10.0 out of 10, Exceptional, (27)
"A wonderful experience……….breakfast overlooking the property, the beautiful flowers grown by the innkeepers, decorated to perfection, with owners there to make your stay as comfortable as possible! "
The price is AED 1,561
AED 1,712 total
includes taxes & fees
11 Apr - 12 Apr
Inn at Kenmore Hall
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (49)
"Lovely space and welcoming host."
The price is AED 988
AED 1,044 total
includes taxes & fees
7 Apr - 8 Apr
Harbour House Inn
Eastgate Inn B&B
Porch

Eastgate Inn B&B

2.5 star property
9.2 out of 10, Wonderful, (68)
"Lovely Inn and Innkeeper. The room was clean and cozy. There was hot coffee and breakfast in the morning including homemade breads and fruit. We will be back! "
Eastgate Inn B&B
The Red Door B&B
Interior

The Red Door B&B

3.0 star property
10.0 out of 10, Exceptional, (5)
"We loved staying at this b&b. The owners were very accommodating, kind and helpful. Because of the pandemic, they only took us for the weekend. The breakfasts were above and beyond our expectations, simply fantastic. We highly recommend this beautiful place and we will be back for sure. "
The Red Door B&B
Berkshire Mountain House
Comfort Apartment, 1 Bedroom, Mountain View, Garden Area | Private kitchenette | Mini-fridge, paper towels

Berkshire Mountain House

3.0 star property
9.4 out of 10, Exceptional, (24)
"Mona was an excellent host. Our bed was very comfortable and the food was good, too! I'd definitely recommend staying here as there's so much to do in the area."
Berkshire Mountain House
Chambery Inn / 7,000 Sqft Luxury Historic Berkshire landmark on Main Street
9 bedrooms, iron/ironing board, WiFi, bed sheets

Chambery Inn / 7,000 Sqft Luxury Historic Berkshire landmark on Main Street

Chambery Inn / 7,000 Sqft Luxury Historic Berkshire landmark on Main Street
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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Other property types in Pittsfield

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Outdoor dining

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (139)
"We have stayed at this property twice before and have been very pleased with the amount of bedrooms and sleeping available. The property is always very clean and is equipped with everything you need for cooking and dining.the property is a half way point for family members in several directions. "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Hancock Village Inn at Jiminy Peak
Miscellaneous

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
The price is AED 2,196
AED 4,030 total
includes taxes & fees
1 Apr - 2 Apr
Hancock Village Inn at Jiminy Peak
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1792)
"The location to jimney peak was great."
The price is AED 474
AED 560 total
includes taxes & fees
1 Apr - 2 Apr
Vacation Village in the Berkshires
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.

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