Search B&B in Pittsfield

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

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

3.5 star property
9.0 out of 10, Wonderful, (1002)
"The Inn was beautiful and the staff were knowledgeable and friendly "
The price is AED 520
AED 725 total
includes taxes & fees
4 Jun - 5 Jun
The Cornell Inn, Lenox & The Berkshires
Lakehouse Inn
Aerial view

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (262)
"Wonderful Location"
Lakehouse Inn
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (472)
"Great historic inn loaded with interesting common areas and furnishings."
The price is AED 663
AED 811 total
includes taxes & fees
16 Jun - 17 Jun
Whistler's Inn Bed & Breakfast
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)
"The property is so lovely and peaceful. I love the classic mid-century modern aesthetic. For visitors to the National Shrine of Divine Mercy, the Inn’s location couldn’t be more perfect with only a 5-minute walk to the Shrine. "
The price is AED 988
AED 988 total
includes taxes & fees
8 Jun - 9 Jun
Tanglewood Suites
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (412)
"Nice"
The price is AED 536
AED 588 total
includes taxes & fees
4 Jun - 5 Jun
Shaker Mill Inn
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (364)
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
The price is AED 698
AED 779 total
includes taxes & fees
8 Jun - 9 Jun
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, (129)
"Best place I have been. Beautiful place. Excellent host. "
The price is AED 638
AED 713 total
includes taxes & fees
4 Jun - 5 Jun
The Trail in Adams - Berkshires’ Art Hotel
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (125)
"Very enjoyable comfortable stay"
The price is AED 1,025
AED 1,145 total
includes taxes & fees
1 Jun - 2 Jun
Devonfield Inn B&B
Inn at Silver Maple Farm
Aerial view

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (85)
"Everything about our stay in The Loft was wonderful! The hot breakfast each morning was incredible. The entire inn was very clean and well kept. We will definitely be back! "
The price is AED 547
AED 591 total
includes taxes & fees
1 Jun - 2 Jun
Inn at Silver Maple Farm
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (152)
"Very homy kind of Inn. Owner was very accommodative and friendly. Very safe place with great ambience. "
The price is AED 848
AED 947 total
includes taxes & fees
3 Jun - 4 Jun
Brook Farm Inn
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)
"Beautiful place. Everything was perfect and so pretty. Great location, too. Will definitely return. "
The price is AED 1,551
AED 1,733 total
includes taxes & fees
2 Jun - 3 Jun
33 Main
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)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is AED 1,137
AED 1,375 total
includes taxes & fees
2 Jun - 3 Jun
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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! "
Inn at Kenmore Hall
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 Inn at Stockbridge
Granville House
Interior detail

Granville House

3.0 star property
10.0 out of 10, Exceptional, (82)
"Beautiful rooms, wonderful hosts, been here several times and plan to come again. "
The price is AED 1,084
AED 1,210 total
includes taxes & fees
30 Jun - 1 Jul
Granville House
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (49)
"Nice place for a weekend away."
The price is AED 867
AED 917 total
includes taxes & fees
12 Jun - 13 Jun
Harbour House Inn
Eastgate Inn B&B
Porch

Eastgate Inn B&B

2.5 star property
9.2 out of 10, Wonderful, (68)
"Great host and enjoyable stay."
Eastgate Inn 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)
"GORGEOUS Scenery and NICE place to stay !"
Berkshire Mountain House
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
Elegant suite with a king bed, fireplace, and kitchenette.
Living area

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

The price is AED 1,579
AED 2,145 total
includes taxes & fees
4 Jun - 5 Jun
Elegant suite with a king bed, fireplace, and kitchenette.
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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. Tanglewood Suites: 2 rooms. 11.6 mi (18.6 km) from the downtown core. Lakehouse Inn: 14 rooms. Situated 8.5 mi (13.6 km) from the heart of Pittsfield. Enjoy the free full breakfast and deli. Whistler’s Inn Bed & Breakfast: 14 rooms. 6.1 mi (9.8 km) from the heart of downtown. Enjoy the private yard and unique décor. 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.