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Check prices for these dates

Next weekend
Apr 24 - Apr 26
In two weeks
May 1 - May 3
In one month
May 15 - May 17
In two months
Jun 12 - Jun 14

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, (44 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is ￥25,561
￥28,552 total
includes taxes & fees
Apr 16 - Apr 17
Wilder House Berkshires
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (447 reviews)
"Everything was great— the cleanliness, the plentiful breakfast, the character and coziness, and the proximity to Amici across the street (free dessert with your room key)."
United States
Patrick
The price is ￥16,951
￥18,595 total
includes taxes & fees
Apr 22 - Apr 23
Shaker Mill Inn
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (173 reviews)
"Best host (Lucas) makes all the difference! Great views and delicious breakfasts. "
United States
diane
The price is ￥24,484
￥28,157 total
includes taxes & fees
Apr 16 - Apr 17
Blackberry River Inn
Double Room | 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, (5 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 ￥31,768
￥35,485 total
includes taxes & fees
Apr 16 - Apr 17
The Berkshire Mountain 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 ￥27,160
￥30,337 total
includes taxes & fees
Apr 19 - Apr 20
Chambery Inn
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"Beautiful Inn, hosts are most welcome and the breakfast was perfect. Heading back for certain!"
United States
Karen
The price is ￥20,535
￥23,626 total
includes taxes & fees
May 3 - May 4
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 ￥36,025
￥42,254 total
includes taxes & fees
Apr 18 - Apr 19
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, (137 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
The price is ￥47,493
￥53,049 total
includes taxes & fees
Apr 26 - Apr 27
Devonfield Inn B&B
Individually decorated, individually furnished, desk, laptop workspace

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (99 reviews)
"Very cosy and friendly "
United States
Dominic
The price is ￥35,580
￥39,743 total
includes taxes & fees
Apr 16 - Apr 17
Granville House
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 ￥37,312
￥41,677 total
includes taxes & fees
May 3 - May 4
Whistler's Inn Bed & Breakfast
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, (110 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is ￥49,156
￥59,465 total
includes taxes & fees
Apr 29 - Apr 30
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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 ￥16,678
￥19,180 total
includes taxes & fees
Apr 16 - Apr 17
Locust Tree Bed and Breakfast LLC
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 ￥68,266
￥76,252 total
includes taxes & fees
Apr 23 - Apr 24
33 Main
Aerial view

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (103 reviews)
"Great property, very comfortable, incredible staff, easy access to skiing in the area!"
United States
Dominick
The price is ￥22,079
￥24,728 total
includes taxes & fees
Apr 19 - Apr 20
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 ￥34,214
￥44,566 total
includes taxes & fees
May 3 - May 4
Experience Timeless Elegance in The Edith Wharton Room!
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 ￥27,365
￥31,361 total
includes taxes & fees
Apr 16 - Apr 17
Brook Farm 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, (305 reviews)
"Great stay"
United Kingdom
Katherine
The price is ￥42,807
￥48,425 total
includes taxes & fees
Apr 16 - Apr 17
Inn at Pine Plains
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, (116 reviews)
"We had a great stay! Close to Hudson and all the great spots there. Spacious and lovely room. We'll definitely stay here again!"
United States
Jeremy
The price is ￥27,797
￥31,133 total
includes taxes & fees
Apr 16 - Apr 17
Changing Times Boutique Country Lodging
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 ￥67,507
￥74,056 total
includes taxes & fees
May 10 - May 11
Inn at Kenmore Hall
Interior

Elegant Carriage House room with a queen bed and private patio.

Elegant Carriage House room with a queen bed and private patio.
Lenox
The price is ￥41,838
￥54,197 total
includes taxes & fees
May 11 - May 12
Elegant Carriage House room with a queen bed and private patio.
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

Berkshires Untold

Berkshires Untold

10/10 Excellent
"For an old roadside motel they have turned this into the coziest little place. The library is charming, the rooms are cool and comfortable and the food was wonderful. Highly recommend "
Molly 2-night trip
Posted 10 hours ago
Berkshires Untold

Find out more about Sheffield

Sheffield B&B information

Number of reviews
2,527
Accommodation
41 B&B
Lowest Price
￥18,595
Highest Price
￥76,252

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 Mount Everett State Reservation 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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