Search B&B in Pittsfield

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Pittsfield bed & breakfast

A snow-covered outdoor area with a patio, seating, and a covered dining area.

1. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.4 out of 10, Exceptional, (1,002 reviews)
"Lovely room, comfortable bed and a nice breakfast."
United Kingdom
judith
The price is AED 624
AED 716 total
includes taxes & fees
9 Nov - 10 Nov
The Cornell Inn, Lenox & The Berkshires
A red building with a sign reading "Shaker Mill Inn."

2. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (483 reviews)
"Loved the location, fireplace and vibe"
United States
Mahadeva
The price is AED 533
AED 584 total
includes taxes & fees
8 Nov - 9 Nov
Shaker Mill Inn
A garden with a white gazebo, a brick pathway, and various plants and flowers.

3. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.2 out of 10, Very good, (522 reviews)
"Delightful experience in a gilded age setting."
United States
George
The price is AED 506
AED 565 total
includes taxes & fees
7 Nov - 8 Nov
Whistler's Inn Bed & Breakfast
A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

4. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (118 reviews)
"Perfect location for hiking, hanging out and Tanglewood Comfortable and charming common space and cozy nicely decorated rooms Generous breakfast and snacks throughout the day We’ll be back"
United States
Linda
The price is AED 602
AED 675 total
includes taxes & fees
2 Dec - 3 Dec
Inn at Silver Maple Farm
A two-story building with a sign reading "Chambéry Inn".

5. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (390 reviews)
"An absolutely perfect getaway spot! Beautiful rooms, great service, and an ideal location. Highly recommend and we will be going back."
United States
Alexandra
The price is AED 681
AED 760 total
includes taxes & fees
10 Nov - 11 Nov
Chambery Inn
Front of property

6. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (108 reviews)
"Wonderful place… clean, cosy room, comfy bed, friendly staff, great breakfast. Delightful location near Norman Rockwell museum."
United States
Kimberly
The price is AED 981
AED 1,151 total
includes taxes & fees
8 Nov - 9 Nov
The Inn at Stockbridge
A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

7. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (141 reviews)
"Wonderful location and hosts are amazing. Breakfast was great. Clean."
United States
Sebastien
The price is AED 1,355
AED 1,514 total
includes taxes & fees
13 Nov - 14 Nov
Devonfield Inn B&B
A wooden cabin interior with a dining area featuring two white chairs, a table with a coffee pot and a cup, and a view into the kitchen through an open doorway.

8. The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.2 out of 10, Wonderful, (159 reviews)
"Fun decor, friendly staff, great complimentary breakfast, directly on bike path."
United States
Susan
The price is AED 632
AED 706 total
includes taxes & fees
7 Dec - 8 Dec
The Trail in Adams - Berkshires’ Art Hotel
A well-appointed bedroom with a large bed, a bedside table, a chair, and a bathroom visible through an open door.

9. 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 997
AED 1,242 total
includes taxes & fees
9 Nov - 10 Nov
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
A two-story house with a brick entrance and a white facade.

10. 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
9.4 out of 10, Exceptional, (120 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is AED 1,403
AED 1,697 total
includes taxes & fees
26 Nov - 27 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

11. Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.6 out of 10, Exceptional, (178 reviews)
"Breakfast was not only delicious, the room was sweet and bright and staff very attentive."
United States
Carrie
The price is AED 608
AED 709 total
includes taxes & fees
1 Dec - 2 Dec
Brook Farm Inn
A dining table with pastries, a coffee pot, and a vase of sunflowers.

12. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (110 reviews)
"We loved everything about Granville House, especially the innkeepers! Wonderful atmosphere and excellent food! It was definitely the highlight of our trip to New England."
United States
Cynthia
The price is AED 937
AED 1,046 total
includes taxes & fees
18 Nov - 19 Nov
Granville House
A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

13. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is AED 997
AED 1,242 total
includes taxes & fees
9 Nov - 10 Nov
Experience Timeless Elegance in The Edith Wharton Room!
A room with a dark green sofa, a small table with a vase of flowers, a desk with a lamp, and a window with curtains.

14. 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 1,056
AED 1,305 total
includes taxes & fees
8 Nov - 9 Nov
Elegant Carriage House room with a queen bed and private patio.
A porch with a white railing, a potted plant, and a view of a garden.

15. 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 1,114
AED 1,385 total
includes taxes & fees
15 Nov - 16 Nov
Cozy Carriage House room with a double bed and private balcony
A wooden deck with Adirondack chairs and a small table, leading to a garden area with a swing set.

16. Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is AED 1,173
AED 1,452 total
includes taxes & fees
8 Nov - 9 Nov
Historic Susan B. Anthony Room - Cozy & Charming Stay
A bedroom with a bed, a fireplace, a ceiling fan, and a door.

17. 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 1,438
AED 1,788 total
includes taxes & fees
8 Nov - 9 Nov
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
A bedroom with a bed, a television, a fireplace, and a window.

18. "Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is AED 1,555
AED 1,877 total
includes taxes & fees
8 Nov - 9 Nov
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
A modern living room with a sofa, a coffee table, and a fireplace.

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

Elegant suite with a king bed, fireplace, and kitchenette.
Lenox
The price is AED 1,731
AED 2,142 total
includes taxes & fees
8 Nov - 9 Nov
Elegant suite with a king bed, fireplace, and kitchenette.
A modern living room with a sloped ceiling, a sofa, a coffee table, and a unique chandelier.

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

Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Lenox
The price is AED 1,731
AED 2,150 total
includes taxes & fees
15 Nov - 16 Nov
Experience Luxury in The Lady Cicely Grand Suite 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.
View all properties

Learn more about Pittsfield

Nestled in the heart of the Berkshires, this cultural hub boasts the renowned Berkshire Museum and historic Colonial Theatre. Outdoor enthusiasts can hike nearby Pittsfield State Forest trails before exploring the vibrant downtown's farm-to-table restaurants and local art galleries.

See all hotels in Pittsfield
A historic building with a clock, a flag, and a street lamp.

Top reviews in Pittsfield

A snow-covered outdoor area with a patio, seating, and a covered dining area.
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox

10/10 Excellent

VERY friendly staff and location for area attractions.
United States
Lawrence
Reviewed February 12, 2023
The Cornell Inn, Lenox & 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. The Trail in Adams - Berkshires’ Art Hotel: 9 rooms. 13.8 mi (22.2 km) from the heart of downtown. Enjoy the unique décor and patio area. 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 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.

Explore a world of travel with Expedia