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

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, (62)
"I love the fact that it only had eight rooms they had happy hour from 5 to 6 PM so we are able to meet other people at the hotel. I love the rooms and the cleanliness and especially the breakfast they were amazing and delicious!! I would recommend this hotel highly!"
The price is NT$12,533
per night
May 12 - May 13
33 Main
Front of property - evening/night
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (106)
"The classic character of the Inn is so beautiful and adds to the whole experience!"
The price is NT$9,029
per night
May 5 - May 6
Devonfield Inn B&B
Interior detail
Granville House
4.0 star property
10.0 out of 10, Exceptional, (68)
"It is a very nice location and we felt very comfortable during our stay . The included breakfast was delicious and we felt like royalty during our stay. "
The price is NT$6,472
per night
May 7 - May 8
Granville House
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Lobby
Inn at Kenmore Hall
3.0 star property
10.0 out of 10, Exceptional, (25)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
Inn at Kenmore Hall
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
Aerial view
Inn at Silver Maple Farm
3.0 star property
9.8 out of 10, Exceptional, (67)
"I had a wonderful stay here with my sister. I would definitely go back next time i am in the area"
The price is NT$4,844
per night
May 5 - May 6
Inn at Silver Maple Farm
Aerial view
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, (150)
"Love this Inn, all employees were friendly and knowledgeable about things to do in the area. The breakfast was delicious . I look forward to staying at the Inn again."
The price is NT$4,389
per night
May 5 - May 6
Lakehouse Inn
Garden
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (380)
"This is a lovely place to say. Very warm and welcoming. The staff was very helpful and even brought a little doggy basket for my dog. It included a blanket, dog bowls treats and more!! Had a very very nice time. "
The price is NT$3,041
per night
May 5 - May 6
Shaker Mill Inn
Exterior
The Inn at Stockbridge
4.0 star property
9.6 out of 10, Exceptional, (92)
"Great B&B with everything you need especially for a quick getaway to vist Stockbridge & Great Barrington Massachusetts. The new owners have added new touches to this Inn and the pride of ownership shows. Highly recommended 👌 "
The Inn at Stockbridge
Junior Suite | Premium bedding, individually decorated, desk, iron/ironing board
The Barrington
4.0 star property
9.6 out of 10, Exceptional, (95)
"Great stay, the room was as advertised, delicious breakfast included and great location. Will stay again. "
The price is NT$10,517
per night
May 10 - May 11
The Barrington
Front of property
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (356)
"Amazing place.."
The price is NT$7,776
per night
May 10 - May 11
Chambery Inn
Front of property
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (134)
"Wonderful hospitality. Amazing breakfast. Will be back!!"
The price is NT$5,061
per night
May 7 - May 8
Brook Farm Inn
Exterior
Harbour House Inn
3.5 star property
9.4 out of 10, Exceptional, (48)
"Decorations were beautiful, room and bed were so comfortable, hostess and food were wonderful. Brandi was thoughtful in every way possible. Can't go wrong choosing this place over a chain. Love it!"
The price is NT$8,001
per night
May 7 - May 8
Harbour House Inn
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, (101)
"The b&b was so beautiful and unique! The area was serene. The host was very sweet and accommodating."
The price is NT$13,047
per night
May 4 - May 5
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Comfort Apartment, 1 Bedroom, Mountain View, Garden Area | Private kitchenette
Berkshire Mountain House
3.0 star property
9.2 out of 10, Wonderful, (21)
"We had a wonderful stay with Mona and Phil , we made new friends."
Berkshire Mountain House
Porch
Eastgate Inn B&B
2.5 star property
9.0 out of 10, Wonderful, (64)
"The owner, Daliya, is very friendly and helpful, with good advice. We enjoyed the breakfasts."
Eastgate Inn B&B
Room | Rollaway beds, free WiFi
Federal House Inn
3.5 star property
9.0 out of 10, Wonderful, (406)
"Beautiful old house. Personable, helpful and accommodating staff. Wonderful homemade breakfast, wine hour and snacks. We had a great stay."
Federal House Inn
Lounge
Mile Hill B&B
3.5 star property
9.0 out of 10, Wonderful, (23)
"Our hostess was very lovely and so was her beautiful cat! Scones and delicious breakfast. Lovely outdoor area with singing birds and chipmunks! Very private and lovely bathroom. Comfortable bed for 2! A wonderful stay."
Mile Hill B&B
Terrace/patio
The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
8.8 out of 10, Excellent, (103)
"It was clean and quiet good Breakfast "
The price is NT$7,111
per night
May 5 - May 6
The Trail in Adams - Berkshires’ Art Hotel
Porch
The Cornell Inn, Lenox
3.0 star property
8.6 out of 10, Excellent, (1000)
"Great breakfast. "
The price is NT$3,948
per night
May 12 - May 13
The Cornell Inn, Lenox
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See all available properties in Pittsfield
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.

Other property types in Pittsfield

Indoor pool, outdoor pool, pool umbrellas
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1672)
"Very nice spot quiet "
The price is NT$5,486
per night
May 4 - May 5
Vacation Village in the Berkshires
2 Bedroom Condo 1/2 mile from base | Private kitchen | Microwave, stovetop, coffee/tea maker, toaster
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (856)
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"
The price is NT$4,822
per night
May 7 - May 8
Jiminy Peak Mountain Resort
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.

Pittsfield B&B information

Number of reviews
2,387
Accommodation
24 B&B
Lowest Price
NT$3,041
Highest Price
NT$13,047

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. While you’re here, you can get to know Pittsfield by exploring its natural beauty. Consider a stop by Pittsfield State Forest and Canoe Meadows Wildlife Sanctuary.
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: 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. Inn at Silver Maple Farm: 11 rooms. 10.9 mi (17.5 km) from the heart of downtown. Enjoy the free buffet breakfast and designer toiletries. 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 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.

Recent reviews of Pittsfield hotels
Expedia verified reviews

The Williams Inn

The Williams Inn

5/5 Excellent
"Love the Williams Inn"
A verified traveler stayed at The Williams Inn
Posted 23 hours ago
The Williams Inn