A historic building with classical architecture, a traffic light, and a yellow taxi.

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Check prices for these dates

Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1
In one month
Nov 13 - Nov 15
In two months
Dec 11 - Dec 13

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
9.2 out of 10, Wonderful, (1,001 reviews)
"Lovely room, comfortable bed and a nice breakfast."
United Kingdom
judith
The price is CA $218
CA $250 total
includes taxes & fees
Oct 27 - Oct 28
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, (479 reviews)
"Very nice Inn in West Stockbridge. Easy walk to center of town and short drive to all the Berkshires attractions. Room was very quiet and the grounds are wonderful. Highly recommended!"
United States
Steven
The price is CA $179
CA $196 total
includes taxes & fees
Nov 16 - Nov 17
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
8.0 out of 10, Very good, (519 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
The price is CA $268
CA $299 total
includes taxes & fees
Oct 19 - Oct 20
Whistler's Inn Bed & Breakfast
An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

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 CA $247
CA $277 total
includes taxes & fees
Nov 8 - Nov 9
Inn at Silver Maple Farm
A wooden deck with a table and chairs, surrounded by a metal railing, overlooking a lush green landscape with trees.

5. The Red Door B&B

The Red Door B&B
3.0 star property
Lee
10.0 out of 10, Exceptional, (5 reviews)
"Centrally located. Lovely hosts. Only three bedrooms so we got to know the other guests. The breakfasts were works of art as well as delicious."
United States
Anonymous traveller
The price is CA $250
CA $398 total
includes taxes & fees
Oct 26 - Oct 27
The Red Door B&B
Front of property

6. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (107 reviews)
"Lovely grounds, property.. room was lovely. Delicious breakfast friendly helpful owners and staff great location"
United States
Jodi
The price is CA $518
CA $607 total
includes taxes & fees
Nov 1 - Nov 2
The Inn at Stockbridge
A two-story building with a sign reading "Chambéry Inn".

7. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (388 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 CA $319
CA $356 total
includes taxes & fees
Oct 26 - Oct 27
Chambery Inn
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
9.0 out of 10, Wonderful, (157 reviews)
"Fun decor, friendly staff, great complimentary breakfast, directly on bike path."
United States
Susan
The price is CA $227
CA $254 total
includes taxes & fees
Nov 16 - Nov 17
The Trail in Adams - Berkshires’ Art Hotel
A large, two-story house with a well-maintained lawn and a fence.

9. 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 CA $524
CA $585 total
includes taxes & fees
Nov 2 - Nov 3
Devonfield Inn B&B
A well-appointed bedroom with a large bed, a bedside table, a chair, and a bathroom visible through an open door.

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is CA $352
CA $461 total
includes taxes & fees
Oct 27 - Oct 28
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
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
9.4 out of 10, Exceptional, (177 reviews)
"Breakfast was not only delicious, the room was sweet and bright and staff very attentive."
United States
Carrie
The price is CA $276
CA $320 total
includes taxes & fees
Nov 15 - Nov 16
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, (108 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 CA $361
CA $404 total
includes taxes & fees
Oct 25 - Oct 26
Granville House
A two-story house with a brick entrance and a white facade.

13. 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
9.2 out of 10, Wonderful, (119 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is CA $482
CA $584 total
includes taxes & fees
Nov 1 - Nov 2
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

14. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is CA $352
CA $461 total
includes taxes & fees
Oct 27 - Oct 28
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.

15. 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 CA $408
CA $533 total
includes taxes & fees
Nov 11 - Nov 12
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.

16. 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 CA $431
CA $564 total
includes taxes & fees
Nov 1 - Nov 2
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.

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

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is CA $453
CA $593 total
includes taxes & fees
Nov 1 - Nov 2
Historic Susan B. Anthony Room - Cozy & Charming Stay
A bedroom with a bed, a fireplace, a ceiling fan, and a door.

18. 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 CA $555
CA $726 total
includes taxes & fees
Nov 1 - Nov 2
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
A bedroom with a bed, a television, a fireplace, and a window.

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

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is CA $601
CA $768 total
includes taxes & fees
Nov 1 - Nov 2
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
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 CA $669
CA $874 total
includes taxes & fees
Nov 1 - Nov 2
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.
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Top Pittsfield Hotel Reviews

FairBridge Inn Express

FairBridge Inn Express

10/10 Excellent
"This motel was well-cared for and a good value compared to anywhere close boy on our early-October Saturday night in the busy Berkshires!"
Richard 1-night trip
Posted 9 hours ago
FairBridge Inn Express

Find out more about Pittsfield

Pittsfield B&B information

Number of reviews
1,907
Accommodation
35 B&B
Lowest Price
CA $196
Highest Price
CA $876

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.

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