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Check prices for these dates

Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct
In one month
23 Oct - 25 Oct
In two months
20 Nov - 22 Nov

Our top choices for Pittsfield bed & breakfast

Terrace/patio

1. 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 AED 666
AED 744 total
includes taxes & fees
28 Sep - 29 Sep
The Trail in Adams - Berkshires’ Art Hotel
Exterior

2. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (56 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is AED 867
AED 916 total
includes taxes & fees
24 Sep - 25 Sep
Harbour House Inn
Front of property

3. 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 AED 942
AED 1,052 total
includes taxes & fees
29 Sep - 30 Sep
Chambery Inn
Front of property - evening/night

4. 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 1,612
AED 1,801 total
includes taxes & fees
24 Sep - 25 Sep
Devonfield Inn B&B
Front of property

5. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (106 reviews)
"Lovely grounds, property.. room was lovely. Delicious breakfast friendly helpful owners and staff great location"
United States
Jodi
The price is AED 1,564
AED 1,834 total
includes taxes & fees
23 Sep - 24 Sep
The Inn at Stockbridge
Property grounds

6. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (518 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
The price is AED 542
AED 606 total
includes taxes & fees
23 Sep - 24 Sep
Whistler's Inn Bed & Breakfast
1 bedroom, WiFi, bed sheets

7. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is AED 967
AED 1,266 total
includes taxes & fees
24 Sep - 25 Sep
Experience Timeless Elegance in The Edith Wharton Room!
Garden

8. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (474 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is AED 651
AED 714 total
includes taxes & fees
23 Sep - 24 Sep
Shaker Mill Inn
3 bedrooms, bed sheets

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 967
AED 1,266 total
includes taxes & fees
23 Sep - 24 Sep
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Interior

10. 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 1,085
AED 1,409 total
includes taxes & fees
24 Sep - 25 Sep
Cozy Carriage House room with a double bed and private balcony
Desk, laptop workspace, iron/ironing board (on request), WiFi (free)

11. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (106 reviews)
"Beautiful home with warm and friendly hosts. The rooms were tastefully designed, the bed was very comfortable and the large bathroom was luxurious. The breakfast was absolutely delicious. We will definitely stay again next time we are in Great Barrington. "
United States
Nicole
The price is AED 823
AED 919 total
includes taxes & fees
27 Sep - 28 Sep
Granville House
Exterior

12. 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)
"Convenient location for Tanglewood and other Berkshire sights. Nice complimentary breakfast and arrival cocktail."
United States
Rosann
The price is AED 604
AED 693 total
includes taxes & fees
23 Sep - 24 Sep
The Cornell Inn, Lenox & The Berkshires
Terrace/patio

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

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is AED 1,144
AED 1,484 total
includes taxes & fees
24 Sep - 25 Sep
Historic Susan B. Anthony Room - Cozy & Charming Stay
Interior

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 1,232
AED 1,606 total
includes taxes & fees
27 Sep - 28 Sep
Elegant Carriage House room with a queen bed and private patio.
Living area

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

Elegant suite with a king bed, fireplace, and kitchenette.
Lenox
The price is AED 1,702
AED 2,207 total
includes taxes & fees
24 Sep - 25 Sep
Elegant suite with a king bed, fireplace, and kitchenette.
1 bedroom, bed sheets

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

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is AED 1,908
AED 2,418 total
includes taxes & fees
20 Oct - 21 Oct
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
1 bedroom, bed sheets

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 1,614
AED 2,110 total
includes taxes & fees
28 Sep - 29 Sep
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Fireplace

18. 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 1,908
AED 2,492 total
includes taxes & fees
27 Sep - 28 Sep
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Suite, Private Bathroom (RedBird Suite) | View from room

19. 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, (118 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is AED 1,897
AED 2,295 total
includes taxes & fees
12 Oct - 13 Oct
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Aerial view

20. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (117 reviews)
"We had a very pleasant stay at this. Eautiful country property. Check in was smooth and instructions were easy to follow. Our room, in the main building was well appointed. The bed was super comfortable and the amenities were fine. Breakfast was great! Common areas were lovely and inviting, and the s’mores kits in the lobby were just the thing for an evening around the outdoor fire pit. Highly recommend for anyone seeking a serene country setting."
United States
Jody
The price is AED 749
AED 839 total
includes taxes & fees
23 Sep - 24 Sep
Inn at Silver Maple Farm
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

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

8/10 Good
"There is no check-in desk. Had to call the phone number provided at the entrance door to be let in. Arrived 8pm. Clean, spacious suite with fully equipped kitchen. Wifi worked well."
Vladislav 1-night trip
Posted less than an hour ago
The Central Downtown Inn & Suites

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 Hancock Shaker Village are worthy sites to check out. You might put Bousquet Ski Area and Pontoosuc Lake 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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