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

Bed and Breakfast in Sheffield

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Check prices for these dates

Next weekend
17 Jul - 19 Jul
In two weeks
24 Jul - 26 Jul
In one month
7 Aug - 9 Aug
In two months
4 Sept - 6 Sept

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, (56 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is NZ$340
includes taxes & fees
19 July - 20 July
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, (429 reviews)
"Below average B&B"
United States
Larry
The price is NZ$212
includes taxes & fees
19 July - 20 July
Locust Tree Bed and Breakfast LLC
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (191 reviews)
"beautiful inn"
United States
Maura
The price is NZ$289
includes taxes & fees
13 July - 14 July
Blackberry River Inn
Property grounds

Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (504 reviews)
"Beautiful inn with the most interesting treasures and decorations."
United States
Mary
The price is NZ$314
includes taxes & fees
13 July - 14 July
Whistler's Inn Bed & Breakfast
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,006 reviews)
"The staff were super friendly"
United States
John
The price is NZ$437
includes taxes & fees
13 July - 14 July
The Cornell Inn, Lenox & The Berkshires
Aerial view

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (111 reviews)
"Very nice hotel."
United States
Erdem
The price is NZ$393
includes taxes & fees
13 July - 14 July
Inn at Silver Maple Farm
Exterior

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
9.0 out of 10, Wonderful, (9 reviews)
"The new owners have done a great job. The place is immaculate, the room was very comfortable and well appointed, the common areas charming. Highly recommended."
United States
Robert
The price is NZ$518
includes taxes & fees
15 July - 16 July
The Berkshire Mountain Inn
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 NZ$545
includes taxes & fees
12 July - 13 July
Inn at Pine Plains
Deluxe Room, 1 King Bed, Ensuite (2nd Floor)

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (119 reviews)
"The place is so authentic and beautiful, the owner is so kind and friendly, and we had really good experience "
United States
Tamir
The price is NZ$393
includes taxes & fees
12 July - 13 July
Changing Times Boutique Country Lodging
Individually decorated, individually furnished, desk, laptop workspace

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 NZ$538
includes taxes & fees
15 July - 16 July
Granville House
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 NZ$787
includes taxes & fees
20 July - 21 July
The Inn at Stockbridge
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (463 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is NZ$386
includes taxes & fees
12 July - 13 July
Shaker Mill Inn
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 NZ$529
includes taxes & fees
13 July - 14 July
Chambery Inn
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, (112 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is NZ$700
includes taxes & fees
22 July - 23 July
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (167 reviews)
"Lovely stay!"
United States
Jiacheng
The price is NZ$447
includes taxes & fees
15 July - 16 July
Brook Farm 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, (138 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is NZ$860
includes taxes & fees
13 July - 14 July
Devonfield Inn B&B
Luxury Room, 1 King Bed, Bathtub

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 NZ$1,341
includes taxes & fees
23 July - 24 July
33 Main
Miscellaneous

Jenny's Country Manor

Jenny's Country Manor
2.0 star property
Red Hook
7.6 out of 10, Good, (135 reviews)
The price is NZ$278
includes taxes & fees
12 July - 13 July
Jenny's Country Manor
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 NZ$585
includes taxes & fees
27 July - 28 July
Manor House Inn
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 Yankee Inn

The Yankee Inn

8/10 Good
"The hotel is a few minutes from Tanglewood and the Berkshire hotspots. Super friendly staff. Very accommodating. The place is a bit dated, but that has a retro charm like places on the Cape. The grounds are lovely. The breakfast is like other hotel breakfast. Lots of options: cereal, oatmeal, eggs, sausage, hard boiled eggs, fruit, bread, pastries, etc. My only complaint was the bed, which had a mattress in desperate need of replacement. We referred to it as sleeping in the valley because it made us roll to the center. It was also really high, which was challenging in an accessible room. I called and they had a stool for me within 5 minutes so we made it work. The people were so nice so I hate adding a complaint in my review. We would have asked for a room change but were there over a holiday weekend and I was pretty sure there wouldn’t be another option. The pluses outweigh the negatives so we had a good time."
Jean 3-night trip
Posted 10 hours ago
The Yankee Inn

Find out more about Sheffield

Sheffield B&B information

Number of reviews
4,441
Accommodation
41 B&B
Lowest Price
NZ$212
Highest Price
NZ$1,341

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. Locust Tree Bed and Breakfast LLC: 7 rooms. Situated 6.8 mi (11 km) from the heart of Sheffield. Blackberry River Inn: 14 rooms. 9.2 mi (14.9 km) from the city centre. Enjoy the free cooked breakfast and outdoor pool. Shaker Mill Inn: 9 rooms. Located 15.6 mi (25.1 km) from the core of Sheffield.
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 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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