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

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Check prices for these dates

Next weekend
3 Jul - 5 Jul
In two weeks
10 Jul - 12 Jul
In one month
24 Jul - 26 Jul
In two months
21 Aug - 23 Aug

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 AED 637
AED 712 total
includes taxes & fees
7 Jul - 8 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, (426 reviews)
"Below average B&B"
United States
Larry
The price is AED 386
AED 444 total
includes taxes & fees
28 Jun - 29 Jun
Locust Tree Bed and Breakfast LLC
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (190 reviews)
"beautiful inn"
United States
Maura
The price is AED 519
AED 597 total
includes taxes & fees
28 Jun - 29 Jun
Blackberry River Inn
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 AED 1,056
AED 1,172 total
includes taxes & fees
1 Jul - 2 Jul
Manor House Inn
Exterior

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
8.8 out of 10, Excellent, (8 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 AED 972
AED 1,085 total
includes taxes & fees
15 Jul - 16 Jul
The Berkshire Mountain Inn
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (380 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 AED 992
AED 1,108 total
includes taxes & fees
30 Jun - 1 Jul
Chambery 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, (501 reviews)
"This family owned Inn is absolutely charming and the owners are so nice! I will definitely stay here again when I visit the Berkshires."
United States
Stacey
The price is AED 691
AED 772 total
includes taxes & fees
5 Jul - 6 Jul
Whistler's Inn Bed & Breakfast
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 AED 1,010
AED 1,128 total
includes taxes & fees
29 Jun - 30 Jun
Granville House
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 AED 1,539
AED 1,719 total
includes taxes & fees
30 Jun - 1 Jul
Devonfield Inn B&B
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
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 AED 1,556
AED 1,825 total
includes taxes & fees
30 Jun - 1 Jul
The Inn at Stockbridge
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, (111 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is AED 1,213
AED 1,467 total
includes taxes & fees
15 Jul - 16 Jul
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (462 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is AED 606
AED 665 total
includes taxes & fees
1 Jul - 2 Jul
Shaker Mill Inn
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 AED 2,623
AED 2,930 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, (1,002 reviews)
"Great place, nice amenities and convenient location, highly recommended."
United States
Arthur
The price is AED 778
AED 895 total
includes taxes & fees
20 Jul - 21 Jul
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, (109 reviews)
"Very nice hotel."
United States
Erdem
The price is AED 768
AED 860 total
includes taxes & fees
8 Jul - 9 Jul
Inn at Silver Maple Farm
1 bedroom, WiFi, bed sheets, wheelchair access

Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is AED 1,203
AED 1,572 total
includes taxes & fees
29 Jun - 30 Jun
Experience Timeless Elegance in The Edith Wharton Room!
Free daily continental breakfast

Inn at Pine Plains

Inn at Pine Plains
3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (307 reviews)
"Great stay"
United Kingdom
Katherine
The price is AED 950
AED 1,075 total
includes taxes & fees
28 Jun - 29 Jun
Inn at Pine Plains
Lobby

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
Richmond
10.0 out of 10, Exceptional, (28 reviews)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is AED 1,561
AED 1,712 total
includes taxes & fees
29 Jun - 30 Jun
Inn at Kenmore Hall
Deluxe Room, 1 King Bed, Ensuite (2nd Floor) | 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, (118 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 AED 716
AED 802 total
includes taxes & fees
28 Jun - 29 Jun
Changing Times Boutique Country Lodging
Interior

Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony
Lenox
The price is AED 1,467
AED 1,917 total
includes taxes & fees
1 Jul - 2 Jul
Cozy Carriage House room with a double bed and private balcony
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 Alander

the Alander

10/10 Excellent
"A lovely place. Lots of cute amenities. The linens and towels were outstanding. I really appreciated that it’s all one level (I hate stairs) and one can park at or near one’s room. Lots of great grass for walking dogs and outdoor seating areas. I would only say that my room, a “junior” was Quite tiny so I would not advise it for more than one person as there was no chair or dresser —just the bed and a small bedside table and small fridge and precious little floor space. Also someone did a really bad paint job in there (room 9) which was odd because everything was so new and trying to be upscale."
Pam 2-night trip
Posted 1 hour ago
the Alander

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, Bartholomews Cobble and Thom Reed UFO Monument Park 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. 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 heart of downtown. 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.
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 Bartholomews Cobble are some notable spots. You might 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?
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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