Search B&B in Sheffield

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Our top choices for Sheffield bed & breakfast

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (43 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is P11,202
P12,513 total
includes taxes & fees
Feb 18 - Feb 19
Wilder House Berkshires

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (415 reviews)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is P6,101
P7,017 total
includes taxes & fees
Feb 14 - Feb 15
Locust Tree Bed and Breakfast LLC

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (110 reviews)
"Great experience, looking forward to staying again."
United States
Greg
The price is P8,135
P9,111 total
includes taxes & fees
Feb 22 - Feb 23
Changing Times Boutique Country Lodging

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (168 reviews)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is P9,550
P10,983 total
includes taxes & fees
Feb 16 - Feb 17
Blackberry River Inn

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (292 reviews)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is P8,368
P9,814 total
includes taxes & fees
Feb 15 - Feb 16
Lakehouse Inn

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
The price is P11,622
P12,981 total
includes taxes & fees
Feb 15 - Feb 16
The Berkshire Mountain Inn

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (375 reviews)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn

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 P13,876
P16,275 total
includes taxes & fees
Feb 22 - Feb 23
The Inn at Stockbridge

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
Brook Farm Inn

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (135 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (95 reviews)
"Absolutely magical at Christmas time! It was only for a quick overnight but felt like time stood still while we were there. The service was impeccable and Terry and Terri were a delight! I look forward to returning. "
United States
Jennifer
The price is P10,111
P11,294 total
includes taxes & fees
Feb 17 - Feb 18
Granville House

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (445 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
The price is P6,470
P7,098 total
includes taxes & fees
Mar 2 - Mar 3
Shaker Mill Inn

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 P23,824
P26,612 total
includes taxes & fees
Mar 1 - Mar 2
33 Main

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 P17,983
P21,754 total
includes taxes & fees
Feb 27 - Feb 28
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (101 reviews)
"Great property, very comfortable, incredible staff, easy access to skiing in the area!"
United States
Dominick
The price is P8,077
P9,046 total
includes taxes & fees
Mar 3 - Mar 4
Inn at Silver Maple Farm

Inn at Pine Plains

Inn at Pine Plains
3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (303 reviews)
"Great stay"
United Kingdom
Katherine
The price is P14,382
P16,269 total
includes taxes & fees
Feb 15 - Feb 16
Inn at Pine Plains

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,001 reviews)
"The Inn was very nice and the staff was super friendly and attentive."
United States
Steven
The price is P7,755
P8,922 total
includes taxes & fees
Feb 16 - Feb 17
The Cornell Inn, Lenox & The Berkshires
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Sheffield Hotel Reviews

Find out more about Sheffield

Sheffield B&B information

Number of reviews
3,442
Accommodation
26 B&B
Lowest Price
P7,017
Highest Price
P26,612

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. Lakehouse Inn: 14 rooms. Situated 15.7 mi (25.2 km) from the heart of Sheffield. Enjoy the free full breakfast and deli. Blackberry River Inn: 14 rooms. 9.2 mi (14.9 km) from the heart of downtown. Enjoy the free cooked breakfast and outdoor pool. Brook Farm Inn: 15 rooms. Located 17.1 mi (27.5 km) from the core of Sheffield. Enjoy the free cooked breakfast and outdoor pool.
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 Drury Preserve 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.

Explore a world of travel with Expedia