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Check prices for these dates

Next weekend
10 Apr - 12 Apr
In two weeks
17 Apr - 19 Apr
In one month
1 May - 3 May
In two months
29 May - 31 May

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, (43 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is S$199
includes taxes & fees
14 Apr - 15 Apr
Wilder House Berkshires
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (446 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
The price is S$142
includes taxes & fees
6 Apr - 7 Apr
Shaker Mill Inn
Individually decorated, iron/ironing board, free WiFi

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
9.6 out of 10, Exceptional, (4 reviews)
"Yes"
United States
MICHAEL
The price is S$216
includes taxes & fees
1 Apr - 2 Apr
The Berkshire Mountain Inn
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (172 reviews)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is S$217
includes taxes & fees
2 Apr - 3 Apr
Blackberry River Inn
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (297 reviews)
"Friendly staff, great location, beautiful views, cozy room."
United States
Elizabeth
The price is S$218
includes taxes & fees
3 Apr - 4 Apr
Lakehouse Inn
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (376 reviews)
"Yes the room was spotless and always the staff is ready to answer any questions that we might have. We have been enjoying the Chambery Inn for many years always had a great stay and again looking for our next visit. Vincent Farricielli and Roibert Modena. "
United States
robert
The price is S$246
includes taxes & fees
1 Apr - 2 Apr
Chambery Inn
Individually decorated, individually furnished, desk, laptop workspace

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (97 reviews)
"Everything about Granville House is delightful. The owners have paid attention to every detail, from the decor and the way the rooms are appointed to the comfortable bed and the delicious hot breakfast."
United States
Ann
The price is S$250
includes taxes & fees
2 Apr - 3 Apr
Granville House
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,001 reviews)
"Beautiful Inn, hosts are most welcome and the breakfast was perfect. Heading back for certain!"
United States
Karen
The price is S$183
includes taxes & fees
16 Apr - 17 Apr
The Cornell Inn, Lenox & The Berkshires
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
The price is S$343
includes taxes & fees
3 Apr - 4 Apr
The Inn at Stockbridge
Living room

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (137 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
The price is S$473
includes taxes & fees
2 Apr - 3 Apr
Devonfield Inn B&B
Exterior

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 S$611
includes taxes & fees
23 Apr - 24 Apr
33 Main
Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (416 reviews)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is S$156
includes taxes & fees
2 Apr - 3 Apr
Locust Tree Bed and Breakfast LLC
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, (110 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is S$482
includes taxes & fees
14 Apr - 15 Apr
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Lobby sitting area

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (102 reviews)
"Great property, very comfortable, incredible staff, easy access to skiing in the area!"
United States
Dominick
The price is S$201
includes taxes & fees
1 Apr - 2 Apr
Inn at Silver Maple Farm
Free daily continental breakfast

Inn at Pine Plains

Inn at Pine Plains
3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (305 reviews)
"Great stay"
United Kingdom
Katherine
The price is S$361
includes taxes & fees
1 Apr - 2 Apr
Inn at Pine Plains
Lobby

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
Richmond
10.0 out of 10, Exceptional, (27 reviews)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is S$812
includes taxes & fees
1 Apr - 2 Apr
Inn at Kenmore Hall
Front of property

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164 reviews)
"Everything was perfect - location and accommodation."
United States
Christopher
The price is S$256
includes taxes & fees
24 Apr - 25 Apr
Brook Farm Inn
Premium bedding, individually decorated, individually furnished, desk

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (113 reviews)
"Great experience, looking forward to staying again."
United States
Greg
The price is S$216
includes taxes & fees
1 Apr - 2 Apr
Changing Times Boutique Country Lodging
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

Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"The Quality Inn in Great Barrington is a good value play. The room we had was clean; the staff was friendly and knowledgeable; and the heating was welcomed on this March day. Breakfast was a weak point, but the coffee was good and available throughout the day. And yes, I would stay there again. "
Leslie 1-night trip
Posted 9 hours ago
Quality Inn Great Barrington

Find out more about Sheffield

Sheffield B&B information

Number of reviews
3,262
Accommodation
30 B&B
Lowest Price
S$142
Highest Price
S$812

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, Thom Reed UFO Monument Park and Bartholomews Cobble 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 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 decor. The Cornell Inn, Lenox & The Berkshires: 18.1 mi (29.1 km) from the city centre. Enjoy the free full breakfast and unique decor. 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 city centre. Lakehouse Inn: 14 rooms. Located 15.7 mi (25.2 km) from the core of Sheffield. Enjoy the free full breakfast and snack bar/deli.
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 Thom Reed UFO Monument Park are some notable spots. You should put Magnolia Bluffs Casino and Ashley House 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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