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Check prices for these dates

Next weekend
4 Sept - 6 Sept
In two weeks
11 Sept - 13 Sept
In one month
25 Sept - 27 Sept
In two months
23 Oct - 25 Oct

Our top choices for Pittsfield bed & breakfast

Garden

1. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (471 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is HK$1,341
HK$1,471 total
includes taxes & fees
8 Sept - 9 Sept
Shaker Mill Inn
Exterior

2. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,004 reviews)
"The entire staff was amazing and the inn was beautiful, we will definitely be back"
United States
Edward
The price is HK$1,549
HK$1,777 total
includes taxes & fees
31 Aug - 1 Sept
The Cornell Inn, Lenox & The Berkshires
Aerial view

3. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (114 reviews)
"Very nice hotel."
United States
Erdem
The price is HK$1,011
HK$1,133 total
includes taxes & fees
31 Aug - 1 Sept
Inn at Silver Maple Farm
Property grounds

4. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (517 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
The price is HK$1,249
HK$1,395 total
includes taxes & fees
13 Sept - 14 Sept
Whistler's Inn Bed & Breakfast
Front of property

5. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (386 reviews)
"The room was clean and very quiet. Breakfast was delivered to our room as requested."
United States
Richard
The price is HK$2,117
HK$2,364 total
includes taxes & fees
31 Aug - 1 Sept
Chambery Inn
Front of property

6. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (104 reviews)
"Our room was very clean and comfortable - exactly what we needed to rest well. Breakfast was excellent and we felt well taken care of. We are grateful for the friendly and welcoming hosts and their staff who listened to every need and graciously provided for us. We’ll definitely return for another stay when we’re in the area."
United Kingdom
Michele
The price is HK$2,956
HK$3,467 total
includes taxes & fees
13 Sept - 14 Sept
The Inn at Stockbridge
Terrace/patio

7. 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, (155 reviews)
"Great central location for travelers there to see the sights."
United States
Jenna
The price is HK$1,431
HK$1,598 total
includes taxes & fees
31 Aug - 1 Sept
The Trail in Adams - Berkshires’ Art Hotel
Front of property – evening/night

8. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (140 reviews)
"Excellent food and helpful staff"
United States
Richard
The price is HK$3,050
HK$3,407 total
includes taxes & fees
3 Sept - 4 Sept
Devonfield Inn B&B
View from room

9. 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, (116 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is HK$2,589
HK$3,131 total
includes taxes & fees
28 Sept - 29 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Interior

10. 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 HK$2,630
HK$3,437 total
includes taxes & fees
8 Sept - 9 Sept
Elegant Carriage House room with a queen bed and private patio.
Room

11. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (105 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 HK$2,156
HK$2,408 total
includes taxes & fees
3 Sept - 4 Sept
Granville House
Front of property

12. Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (173 reviews)
"Breakfast was not only delicious, the room was sweet and bright and staff very attentive."
United States
Carrie
The price is HK$1,995
HK$2,291 total
includes taxes & fees
1 Sept - 2 Sept
Brook Farm Inn
Room

13. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is HK$2,441
HK$3,177 total
includes taxes & fees
31 Aug - 1 Sept
Experience Timeless Elegance in The Edith Wharton Room!
Room

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is HK$2,441
HK$3,177 total
includes taxes & fees
31 Aug - 1 Sept
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Interior

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 HK$2,692
HK$3,500 total
includes taxes & fees
31 Aug - 1 Sept
Cozy Carriage House room with a double bed and private balcony
Terrace/patio

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

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is HK$2,818
HK$3,661 total
includes taxes & fees
31 Aug - 1 Sept
Historic Susan B. Anthony Room - Cozy & Charming Stay
Room

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

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is HK$3,696
HK$4,715 total
includes taxes & fees
1 Sept - 2 Sept
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Living area

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

Elegant suite with a king bed, fireplace, and kitchenette.
Lenox
The price is HK$4,072
HK$5,319 total
includes taxes & fees
1 Sept - 2 Sept
Elegant suite with a king bed, fireplace, and kitchenette.
Room

19. 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 HK$3,382
HK$4,396 total
includes taxes & fees
31 Aug - 1 Sept
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Living area

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 HK$4,072
HK$5,319 total
includes taxes & fees
3 Sept - 4 Sept
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Good experience"
JULIANA C 1-night trip
Posted 5 hours ago
Berkshire Mountain Lodge

Find out more about Pittsfield

Pittsfield B&B information

Number of reviews
1,764
Accommodation
35 B&B
Lowest Price
HK$1,133
Highest Price
HK$5,319

Frequently asked questions

Searching for B&Bs in Pittsfield?
If you're hoping for something a little more offbeat than your standard hotel, a bed and breakfast could be a great option for your trip. 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 best choice for your stay?
With attentive service, opportunities to interact with the owner and tasty breakfasts, B&Bs offer a one-of-a-kind environment.
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 decor. Inn at Silver Maple Farm: 11 rooms. 10.9 mi (17.5 km) from the city centre. Enjoy the free buffet breakfast and designer toiletries. Chambery Inn: 9 rooms. Situated 9.7 mi (15.5 km) from the heart of Pittsfield. Enjoy the private garden and snack bar/deli. The Trail in Adams - Berkshires' Art Hotel: 9 rooms. 13.8 mi (22.2 km) from the city centre. Enjoy the unique decor and patio area. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood: 8 rooms. Located 12.4 mi (19.9 km) from the core of Pittsfield. Enjoy the free full breakfast and outdoor pool.
When is the best time to stay at a B&B in Pittsfield?
When you're dreaming of a trip to Pittsfield, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Pittsfield are January, March, February and November, with each month seeing an average of 18 cm 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 visit. You should 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?
You can plan your excursions in and around Pittsfield ahead of time with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 2.5 mi (4 km) from the heart of the city. Otherwise, look for flights into Hudson, NY (HCC-Columbia County), which is 25.7 mi (41.4 km) away. If you'd like to explore around the area, you may want to rent a car for your trip.

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