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

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Check prices for these dates

Next weekend
24 Jul - 26 Jul
In two weeks
31 Jul - 2 Aug
In one month
14 Aug - 16 Aug
In two months
11 Sep - 13 Sep

Our top choices for Sheffield bed & breakfast

Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (57 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is 5.010.958 ₫
5.597.254 ₫ total
includes taxes & fees
19 Jul - 20 Jul
Wilder House Berkshires
Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (434 reviews)
"Below average B&B"
United States
Larry
The price is 2.756.880 ₫
3.170.412 ₫ total
includes taxes & fees
19 Jul - 20 Jul
Locust Tree Bed and Breakfast LLC
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (193 reviews)
"Excellent breakfast, very nice staff."
United States
Leslie
The price is 4.088.059 ₫
4.701.268 ₫ total
includes taxes & fees
19 Jul - 20 Jul
Blackberry River Inn
Exterior

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
9.2 out of 10, Wonderful, (13 reviews)
"The staff and the cleaness of the facility"
United States
MICHAEL
The price is 7.548.600 ₫
8.431.787 ₫ total
includes taxes & fees
19 Jul - 20 Jul
The Berkshire Mountain Inn
Desk, laptop workspace, iron/ironing board (on request), free WiFi

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (102 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 7.220.400 ₫
8.065.318 ₫ total
includes taxes & fees
27 Jul - 28 Jul
Granville House
Free daily continental breakfast

Inn at Pine Plains

Inn at Pine Plains
3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (308 reviews)
"Great stay"
United Kingdom
Katherine
The price is 7.220.400 ₫
8.168.078 ₫ total
includes taxes & fees
19 Jul - 20 Jul
Inn at Pine Plains
Property grounds

Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (505 reviews)
"Beautiful inn with the most interesting treasures and decorations."
United States
Mary
The price is 4.418.885 ₫
4.935.866 ₫ total
includes taxes & fees
20 Jul - 21 Jul
Whistler's Inn Bed & Breakfast
Deluxe Room, 1 King Bed, Ensuite (2nd Floor) | Premium bedding, desk, laptop workspace, blackout curtains

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (119 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 5.251.200 ₫
5.881.344 ₫ total
includes taxes & fees
10 Aug - 11 Aug
Changing Times Boutique Country Lodging
Suite, Private Bathroom (RedBird Suite) | View from room

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, (113 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is 8.668.944 ₫
10.486.906 ₫ total
includes taxes & fees
2 Aug - 3 Aug
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property

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 8.638.224 ₫
9.588.429 ₫ total
includes taxes & fees
27 Jul - 28 Jul
Manor House Inn
Aerial view

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 5.750.064 ₫
6.440.072 ₫ total
includes taxes & fees
22 Jul - 23 Jul
Inn at Silver Maple Farm
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (464 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is 4.962.384 ₫
5.443.735 ₫ total
includes taxes & fees
22 Jul - 23 Jul
Shaker Mill Inn
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (99 reviews)
"Great spot close to town. Cozy, tasteful, comfortable room. Nice breakfasts and pleasant interaction with the staff. We love the Berkshires and we’ll definitely stay here again."
United States
Stephen
The price is 9.735.725 ₫
11.418.735 ₫ total
includes taxes & fees
27 Jul - 28 Jul
The Inn at Stockbridge
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (381 reviews)
"Location is convenient to walk through downtown Lee and to get to a show at Tanglewood."
United States
Joseph
The price is 7.088.857 ₫
7.918.284 ₫ total
includes taxes & fees
16 Aug - 17 Aug
Chambery Inn
Front of property – evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (139 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is 11.526.384 ₫
12.874.892 ₫ total
includes taxes & fees
21 Jul - 22 Jul
Devonfield Inn B&B
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is 19.332.818 ₫
21.594.758 ₫ total
includes taxes & fees
23 Jul - 24 Jul
33 Main
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"The staff were super friendly"
United States
John
The price is 4.319.007 ₫
4.969.061 ₫ total
includes taxes & fees
23 Jul - 24 Jul
The Cornell Inn, Lenox & The Berkshires
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

The Red Lion Inn

The Red Lion Inn

8/10 Good
"This is a historic property with updates needed for the price. It’s an experience above all else with friendly staff and great food options. And walkable around the quaint town with drinks available on the great large front porch."
lauralee 1-night trip
Posted 19 hours ago
The Red Lion Inn

Find out more about Sheffield

Sheffield B&B information

Number of reviews
4,150
Accommodation
30 B&B
Lowest Price
3.170.412 ₫
Highest Price
21.594.758 ₫

Frequently asked questions

Searching for B&Bs in Sheffield?
If you're looking for something a little quirkier than your standard hotel, a stay at a bed and breakfast could be the perfect alternative for your holiday. If your ideal holiday to Sheffield includes spending lots of time outside, Bartholomews Cobble and Thom Reed UFO Monument Park are good spots to enjoy the scenery.
How do you know if a B&B is the best choice for you?
B&Bs all have a unique charm — whether it's a cosy reading space or a beautiful dining room, the little details are what make bed and breakfasts the perfect escape.
What's the best time of year to 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 temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Sheffield are January, March, February and November, with each month seeing an average of 18 cm of snowfall.
What is there to do in Sheffield?
When you want to spend some time in the great outdoors, Housatonic River and Bartholomews Cobble are some notable spots. You should put Magnolia Bluffs Casino and Bartholomew's Cobble on your list if you want to see more of the area.
How can I get to and around Sheffield?
Mapping out your trip in and around Sheffield is easy 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. Otherwise, look 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 a rental car for your journey.

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