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

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Check prices for these dates

Next weekend
7 Aug - 9 Aug
In two weeks
14 Aug - 16 Aug
In one month
28 Aug - 30 Aug
In two months
25 Sept - 27 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, (59 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is RM717
RM801 total
includes taxes & fees
10 Aug - 11 Aug
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, (435 reviews)
"Below average B&B"
United States
Larry
The price is RM429
RM493 total
includes taxes & fees
30 Jul - 31 Jul
Locust Tree Bed and Breakfast LLC
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (199 reviews)
"Excellent breakfast, very nice staff."
United States
Leslie
The price is RM671
RM772 total
includes taxes & fees
29 Jul - 30 Jul
Blackberry River Inn
Exterior

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
9.0 out of 10, Wonderful, (15 reviews)
"Friendly staff and attention to detail making our stay in a charming inn special"
United States
Kristen
The price is RM1,175
RM1,312 total
includes taxes & fees
6 Aug - 7 Aug
The Berkshire Mountain Inn
Desk, laptop workspace, iron/ironing board (on request), free WiFi

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 RM919
RM1,027 total
includes taxes & fees
29 Jul - 30 Jul
Granville House
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 RM1,346
RM1,494 total
includes taxes & fees
29 Jul - 30 Jul
Manor House Inn
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, (113 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is RM1,349
RM1,632 total
includes taxes & fees
10 Aug - 11 Aug
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (99 reviews)
"Beautifully decorated inside and gorgeous gardens and landscaping outside. A lovely serene spot away from the crowds that are only minutes away in downtown Stockbridge. The breakfasts were plentiful, artfully presented and delicious. Staff were friendly and very competent."
United States
Barbara
The price is RM1,517
RM1,779 total
includes taxes & fees
29 Jul - 30 Jul
The Inn at Stockbridge
Front of property – evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (139 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is RM1,794
RM2,003 total
includes taxes & fees
19 Aug - 20 Aug
Devonfield Inn B&B
Free daily continental breakfast

Inn at Pine Plains

Inn at Pine Plains
3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (310 reviews)
"Great stay"
United Kingdom
Katherine
The price is RM1,124
RM1,271 total
includes taxes & fees
2 Aug - 3 Aug
Inn at Pine Plains
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (383 reviews)
"Location is convenient to walk through downtown Lee and to get to a show at Tanglewood."
United States
Joseph
The price is RM1,103
RM1,232 total
includes taxes & fees
27 Aug - 28 Aug
Chambery Inn
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (465 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is RM809
RM887 total
includes taxes & fees
29 Jul - 30 Jul
Shaker Mill Inn
Premium bedding, desk, laptop workspace, blackout curtains

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (119 reviews)
"Terrific host and freshly cooked to order hot breakfast, beautiful grounds, and dog friendly. Would definitely stay again!"
United States
Jamie
The price is RM817
RM915 total
includes taxes & fees
4 Aug - 5 Aug
Changing Times Boutique Country Lodging
Property grounds

Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (507 reviews)
"Beautiful inn with the most interesting treasures and decorations."
United States
Mary
The price is RM696
RM777 total
includes taxes & fees
29 Jul - 30 Jul
Whistler's Inn Bed & Breakfast
Aerial view

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (112 reviews)
"Very nice hotel."
United States
Erdem
The price is RM936
RM1,048 total
includes taxes & fees
24 Aug - 25 Aug
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, (1,001 reviews)
"The cornel Inn is terrific! Great location near tanglewood, shops snd restaurants. Great breakfast"
United States
Judith
The price is RM898
RM1,033 total
includes taxes & fees
23 Aug - 24 Aug
The Cornell Inn, Lenox & The Berkshires
Premium bedding, iron/ironing board, free WiFi, individually decorated

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (75 reviews)
"This was our second stay at 33 Main. Wonderfully maintain, homey environment, with friendly, welcoming and helpful staff. Welcoming cookies, and beautiful water bottle. They even remembered that we asked for the beach and gave us excellent recommendation. Convenient parking in the back. My only suggestion for improvement is breakfast - last year it was much better."
United States
Tatyana
The price is RM3,056
RM3,414 total
includes taxes & fees
24 Aug - 25 Aug
33 Main
Front of property

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (169 reviews)
"Lovely stay!"
United States
Jiacheng
The price is RM994
RM1,144 total
includes taxes & fees
3 Aug - 4 Aug
Brook Farm Inn
Miscellaneous

Jenny's Country Manor

Jenny's Country Manor
2.0 star property
Red Hook
7.6 out of 10, Good, (135 reviews)
"Very nice staff! Large rooms, convenient location."
United States
Georgi
The price is RM572
RM647 total
includes taxes & fees
2 Aug - 3 Aug
Jenny's Country Manor
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

10/10 Excellent
"First class staff and wonderful breakfast."
Larry 1-night trip
Posted 8 hours ago
The Yankee Inn

Find out more about Sheffield

Sheffield B&B information

Number of reviews
2,089
Accommodation
30 B&B
Lowest Price
RM493
Highest Price
RM3,414

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. Chambery Inn: 9 rooms. Located 14.7 mi (23.7 km) from the core of Sheffield. Enjoy the private garden 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 Suter Farm 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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