FTYTP1 The Upper Sheffield Covered Bridge, Sheffield, Massachusetts, USA

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Check prices for these dates

Next weekend
26 Jun - 28 Jun
In two weeks
3 Jul - 5 Jul
In one month
17 Jul - 19 Jul
In two months
14 Aug - 16 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, (55 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is RM797
RM891 total
includes taxes & fees
23 Jun - 24 Jun
Wilder House Berkshires
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (461 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is RM616
RM676 total
includes taxes & fees
22 Jun - 23 Jun
Shaker Mill Inn
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (186 reviews)
"beautiful inn"
United States
Maura
The price is RM644
RM741 total
includes taxes & fees
22 Jun - 23 Jun
Blackberry River 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, (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 RM807
RM903 total
includes taxes & fees
24 Jun - 25 Jun
Changing Times Boutique Country Lodging
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 RM1,138
RM1,287 total
includes taxes & fees
22 Jun - 23 Jun
Inn at Pine Plains
Aerial view

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (107 reviews)
"Very nice hotel."
United States
Erdem
The price is RM658
RM737 total
includes taxes & fees
23 Jun - 24 Jun
Inn at Silver Maple Farm
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 RM690
RM794 total
includes taxes & fees
22 Jun - 23 Jun
The Cornell Inn, Lenox & The Berkshires
Exterior

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (7 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 RM1,023
RM1,142 total
includes taxes & fees
22 Jun - 23 Jun
The Berkshire Mountain Inn
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 RM1,138
RM1,271 total
includes taxes & fees
22 Jun - 23 Jun
Granville House
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 RM1,366
RM1,652 total
includes taxes & fees
6 Jul - 7 Jul
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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 RM1,029
RM1,149 total
includes taxes & fees
24 Jun - 25 Jun
Whistler's Inn Bed & Breakfast
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, (424 reviews)
The price is RM434
RM500 total
includes taxes & fees
22 Jun - 23 Jun
Locust Tree Bed and Breakfast LLC
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 RM1,494
RM1,753 total
includes taxes & fees
23 Jun - 24 Jun
The Inn at Stockbridge
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (379 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 RM1,117
RM1,248 total
includes taxes & fees
21 Jul - 22 Jul
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, (138 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is RM1,609
RM1,797 total
includes taxes & fees
24 Jun - 25 Jun
Devonfield Inn B&B
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 RM2,387
RM2,666 total
includes taxes & fees
22 Jun - 23 Jun
33 Main
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 RM779
RM903 total
includes taxes & fees
1 Jul - 2 Jul
Brook Farm 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

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Comfortable place; terrific bed; no flaws."
Alan 1-night trip
Posted less than an hour ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Find out more about Sheffield

Sheffield B&B information

Number of reviews
3,482
Accommodation
30 B&B
Lowest Price
RM500
Highest Price
RM2,666

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 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. 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 Bartholomews Cobble are some notable spots. You should put Mount Everett State Reservation and Thom Reed UFO Monument Park 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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