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Check prices for these dates

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

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 P9,745
P10,885 total
includes taxes & fees
Apr 2 - Apr 3
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 P6,601
P7,241 total
includes taxes & fees
Apr 1 - Apr 2
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 P9,083
P10,146 total
includes taxes & fees
Apr 1 - Apr 2
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 P9,429
P10,843 total
includes taxes & fees
Apr 5 - Apr 6
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 P8,927
P10,470 total
includes taxes & fees
Apr 24 - Apr 25
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 P10,384
P11,599 total
includes taxes & fees
Apr 30 - May 1
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 P10,537
P11,770 total
includes taxes & fees
Apr 2 - Apr 3
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 P8,323
P9,576 total
includes taxes & fees
Apr 2 - Apr 3
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 P13,734
P16,109 total
includes taxes & fees
Apr 2 - Apr 3
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 P19,923
P22,254 total
includes taxes & fees
Apr 1 - Apr 2
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 P29,915
P33,415 total
includes taxes & fees
Apr 13 - Apr 14
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 P6,358
P7,312 total
includes taxes & fees
Apr 1 - Apr 2
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 P18,740
P22,671 total
includes taxes & fees
Apr 13 - Apr 14
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 P8,417
P9,427 total
includes taxes & fees
Apr 1 - Apr 2
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 P14,988
P16,955 total
includes taxes & fees
Apr 1 - Apr 2
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 P34,820
P38,198 total
includes taxes & fees
Apr 13 - Apr 14
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 P10,530
P12,065 total
includes taxes & fees
Apr 25 - Apr 26
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 P9,083
P10,173 total
includes taxes & fees
Apr 1 - Apr 2
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 14 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
P7,241
Highest Price
P38,198

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.Lakehouse Inn: 14 rooms. Located 15.7 mi (25.2 km) from the core of Sheffield. Enjoy the free full breakfast 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 Ashley House 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.

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