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Check prices for these dates

Next weekend
14 Aug - 16 Aug
In two weeks
21 Aug - 23 Aug
In one month
4 Sep - 6 Sep
In two months
2 Oct - 4 Oct

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, (152 reviews)
"Great central location for travelers there to see the sights."
United States
Jenna
The price is AED 785
AED 877 total
includes taxes & fees
7 Sep - 8 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, (55 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is AED 890
AED 941 total
includes taxes & fees
7 Sep - 8 Sep
Harbour House Inn
Front of property

3. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (383 reviews)
"Location is convenient to walk through downtown Lee and to get to a show at Tanglewood."
United States
Joseph
The price is AED 992
AED 1,108 total
includes taxes & fees
10 Aug - 11 Aug
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, (140 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is AED 1,429
AED 1,596 total
includes taxes & fees
3 Sep - 4 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, (101 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 AED 1,450
AED 1,701 total
includes taxes & fees
7 Sep - 8 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, (509 reviews)
"Beautiful inn with the most interesting treasures and decorations."
United States
Mary
The price is AED 585
AED 654 total
includes taxes & fees
24 Aug - 25 Aug
Whistler's Inn Bed & Breakfast
Luxury Room, 1 King Bed, Bathtub | Premium bedding, iron/ironing board, WiFi (free), individually decorated

7. 33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (75 reviews)
"This was our second stay at 33 Main. Wonderfully maintain, homey environment, with friendly, welcoming and helpful staff. Welcoming cookies, and beautiful water bottle. They even remembered that we asked for the beach and gave us excellent recommendation. Convenient parking in the back. My only suggestion for improvement is breakfast - last year it was much better."
United States
Tatyana
The price is AED 2,623
AED 2,930 total
includes taxes & fees
31 Aug - 1 Sep
33 Main
Interior

8. 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 1,467
AED 1,917 total
includes taxes & fees
16 Aug - 17 Aug
Elegant Carriage House room with a queen bed and private patio.
Garden

9. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (465 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is AED 780
AED 856 total
includes taxes & fees
10 Aug - 11 Aug
Shaker Mill Inn
Fireplace

10. 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 1,878
AED 2,454 total
includes taxes & fees
25 Aug - 26 Aug
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Living area

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

Elegant suite with a king bed, fireplace, and kitchenette.
Lenox
The price is AED 1,878
AED 2,454 total
includes taxes & fees
25 Aug - 26 Aug
Elegant suite with a king bed, fireplace, and kitchenette.
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, (1,002 reviews)
"The entire staff was amazing and the inn was beautiful, we will definitely be back"
United States
Edward
The price is AED 634
AED 729 total
includes taxes & fees
26 Aug - 27 Aug
The Cornell Inn, Lenox & The Berkshires
1 bedroom, bed sheets

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

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is AED 1,702
AED 2,172 total
includes taxes & fees
26 Aug - 27 Aug
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
1 bedroom, bed sheets

14. 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 1,585
AED 2,055 total
includes taxes & fees
31 Aug - 1 Sep
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
3 bedrooms, bed sheets

15. 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 1,144
AED 1,497 total
includes taxes & fees
25 Aug - 26 Aug
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Interior

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 AED 1,261
AED 1,615 total
includes taxes & fees
31 Aug - 1 Sep
Cozy Carriage House room with a double bed and private balcony
Terrace/patio

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

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is AED 1,320
AED 1,727 total
includes taxes & fees
20 Aug - 21 Aug
Historic Susan B. Anthony Room - Cozy & Charming Stay
1 bedroom, WiFi, bed sheets

18. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is AED 1,144
AED 1,497 total
includes taxes & fees
25 Aug - 26 Aug
Experience Timeless Elegance in The Edith Wharton Room!
Desk, laptop workspace, iron/ironing board (on request), WiFi (free)

19. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (103 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 1,010
AED 1,128 total
includes taxes & fees
17 Aug - 18 Aug
Granville House
Suite, Private Bathroom (RedBird Suite) | View from room

20. 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, (114 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is AED 1,213
AED 1,467 total
includes taxes & fees
24 Aug - 25 Aug
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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

8/10 Good
"Very nice space with a full kitchen. You can definitely stay here for a week comfortably. Personally, I didn’t think the bed or the pillows were that comfortable but other than that, it was great."
Cindy 1-night trip
Posted 10 hours ago
Berkshire Mountain Lodge

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. Shaker Mill Inn: 9 rooms. 9.8 mi (15.8 km) from the downtown core. Chambery Inn: 9 rooms. Situated 9.7 mi (15.5 km) from the heart of Pittsfield. Enjoy the private yard and deli. 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. 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.

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