A covered wooden structure with a sloped roof, surrounded by greenery and trees.

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Check prices for these dates

Next weekend
21 Aug - 23 Aug
In two weeks
28 Aug - 30 Aug
In one month
11 Sep - 13 Sep
In two months
9 Oct - 11 Oct

Our top choices for Sheffield bed & breakfast

Exterior

1. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (438 reviews)
"This is a quiet location and easy to find. It has a working-farm vibe rather than a luxury-vacation vibe. French toast was delicious. Guest meals are prepared in a home kitchen without a dishwasher or secondary sink."
United States
Kay
The price is AED 386
AED 444 total
includes taxes & fees
12 Aug - 13 Aug
Locust Tree Bed and Breakfast LLC
Interior detail

2. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (61 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is AED 766
AED 856 total
includes taxes & fees
27 Aug - 28 Aug
Wilder House Berkshires
Library

3. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (202 reviews)
"Excellent breakfast, very nice staff."
United States
Leslie
The price is AED 684
AED 787 total
includes taxes & fees
12 Aug - 13 Aug
Blackberry River Inn
Desk, laptop workspace, iron/ironing board (on request), WiFi (free)

4. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (104 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
Garden

5. 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 695
AED 762 total
includes taxes & fees
8 Sep - 9 Sep
Shaker Mill Inn
Front of property

6. Manor House Inn

Manor House Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (139 reviews)
"Excellent bed and breakfast, room was clean and comfortable."
United States
Kevin
The price is AED 1,172
AED 1,301 total
includes taxes & fees
31 Aug - 1 Sep
Manor House Inn
Deluxe Room, 1 King Bed, Ensuite (2nd Floor) | Premium bedding, desk, laptop workspace, blackout drapes

7. Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (120 reviews)
"Terrific host and freshly cooked to order hot breakfast, beautiful grounds, and dog friendly. Would definitely stay again!"
United States
Jamie
The price is AED 735
AED 823 total
includes taxes & fees
17 Aug - 18 Aug
Changing Times Boutique Country Lodging
Suite, Private Bathroom (RedBird Suite) | View from room

8. 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
Exterior

9. 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 AED 634
AED 729 total
includes taxes & fees
31 Aug - 1 Sep
The Cornell Inn, Lenox & The Berkshires
Property grounds

10. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very Good, (511 reviews)
"Beautiful inn with the most interesting treasures and decorations."
United States
Mary
The price is AED 585
AED 654 total
includes taxes & fees
1 Sep - 2 Sep
Whistler's Inn Bed & Breakfast
Free daily continental breakfast

11. Inn at Pine Plains

Inn at Pine Plains
3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (313 reviews)
"Great stay"
United Kingdom
Katherine
The price is AED 1,010
AED 1,143 total
includes taxes & fees
12 Aug - 13 Aug
Inn at Pine Plains
Front of property

12. 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
8 Sep - 9 Sep
The Inn at Stockbridge
Front of property - evening/night

13. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (140 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
The price is AED 1,429
AED 1,596 total
includes taxes & fees
3 Sep - 4 Sep
Devonfield Inn B&B
Front of property

14. 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
12 Aug - 13 Aug
Chambery Inn
Miscellaneous

15. Jenny's Country Manor

Jenny's Country Manor
2.0 star property
Red Hook
7.8 out of 10, Good, (136 reviews)
"Very nice staff! Large rooms, convenient location."
United States
Georgi
The price is AED 514
AED 582 total
includes taxes & fees
12 Aug - 13 Aug
Jenny's Country Manor
Aerial view

16. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (112 reviews)
"Very nice hotel."
United States
Erdem
The price is AED 731
AED 819 total
includes taxes & fees
3 Sep - 4 Sep
Inn at Silver Maple Farm
Front of property

17. Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (171 reviews)
"Breakfast was not only delicious, the room was sweet and bright and staff very attentive."
United States
Carrie
The price is AED 976
AED 1,119 total
includes taxes & fees
16 Aug - 17 Aug
Brook Farm Inn
Luxury Room, 1 King Bed, Bathtub | Premium bedding, iron/ironing board, WiFi (free), individually decorated

18. 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 2,361
AED 2,637 total
includes taxes & fees
31 Aug - 1 Sep
33 Main
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 Sheffield Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Very nice facilities. My wife especially enjoyed the warm indoor pool."
Wesley 1-night trip
Posted less than an hour ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Frequently asked questions

Searching for B&Bs in Sheffield?
If you're looking for something a little more offbeat than the traditional hotel experience, a stay at a bed and breakfast might be the perfect option for your getaway. If your ideal vacation to Sheffield includes spending lots of time outside, Thom Reed UFO Monument Park and Bartholomews Cobble are good spots to enjoy the scenery.
How do you know if a B&B is a good option for you?
Every B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook, the little details are what make bed and breakfasts a fun place to get away.
What are the top B&Bs in Sheffield?
Below are some B&Bs in the area: Wilder House Berkshires: 5 rooms. 0.3 mi (0.5 km) from the heart of Sheffield. Enjoy the free cooked breakfast and unique décor. The Cornell Inn, Lenox & The Berkshires: 18.1 mi (29.1 km) from the downtown core. Enjoy the free full breakfast and unique décor. Blackberry River Inn: 14 rooms. Situated 9.2 mi (14.9 km) from the heart of Sheffield. Enjoy the free cooked breakfast and outdoor pool. Locust Tree Bed and Breakfast LLC: 7 rooms. 6.8 mi (11 km) from the heart of downtown.Chambery Inn: 9 rooms. Located 14.7 mi (23.7 km) from the core of Sheffield. Enjoy the private yard and deli.
When should I book my B&B in Sheffield?
When you're dreaming of a escape to Sheffield, 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 28°F. The snowiest months in Sheffield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Sheffield?
When you want to spend some time in the great outdoors, Housatonic River and Thom Reed UFO Monument Park are some notable spots. You might put Magnolia Bluffs Casino and Three Mile Pond Wildlife Management Area on your list if you want to see more of the area.
How can I get to and around Sheffield?
Planning your excursions in and around Sheffield is easier with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 22 mi (35.4 km) away from the heart of the city. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 22.3 mi (35.9 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.