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Compare 27 B&B in Sheffield with updated reviews, rates, and availability.

The Cornell Inn, Lenox
Porch
The Cornell Inn, Lenox
3.0 star property
8.8 out of 10, Excellent, (1001)
"What a pleasure it was to stay at the Cornell Inn! Unfortunately we were only there for one night, but one can definitely get a sense of how a property is even in a shorter timeframe. Now, the real gem at this property is the staff! From our check-in experience with Lorie to our F&B server, Lindsey whi went waaaaay out of her way to help us with an issue we had, and to Paige, front desk assistant manager who tied everything together and made our experience even that much better. I wish I...
The price is NT$3,892
NT$4,565 total
includes taxes & fees
Nov 6 - Nov 7
The Cornell Inn, Lenox
Lakehouse Inn
Aerial view
Lakehouse Inn
4.0 star property
9.8 out of 10, Exceptional, (224)
"This was the perfect getaway for us. We have traveled all over and this was one of my favorite places. The staff was super friendly and courteous. The property was beautiful and the views were breathtaking. Highly recommend if you are in the area and if you’re not make your way there. "
The price is NT$3,988
NT$4,677 total
includes taxes & fees
Nov 7 - Nov 8
Lakehouse Inn
Blackberry River Inn
Library
Blackberry River Inn
3.0 star property
9.6 out of 10, Exceptional, (85)
"Very cute inn with amazing breakfast!"
The price is NT$5,501
NT$6,326 total
includes taxes & fees
Nov 6 - Nov 7
Blackberry River Inn
Locust Tree Bed and Breakfast LLC
Terrace/patio
Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, (365)
"Nice B&B that was close to an event we had at the Great Falls Brewery in Canaan. Very quiet. The bed was clean but here were some cobwebs under the bed and bedstands. The shower/tub also didn't seem to be very clean. In any case, it was affordable and perfect for a night in the CT mountains."
The price is NT$3,350
NT$3,853 total
includes taxes & fees
Nov 6 - Nov 7
Locust Tree Bed and Breakfast LLC
Chambery Inn
Front of property
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (359)
"Lovely, unique property with huge rooms! Such a fun place to stay. "
The price is NT$6,062
NT$6,771 total
includes taxes & fees
Nov 6 - Nov 7
Chambery Inn
Whistler's Inn Bed & Breakfast
Property grounds
Whistler's Inn Bed & Breakfast
3.5 star property
7.8 out of 10, Good, (469)
"This bed and breakfast is a true gem, set in a beautifully preserved 1836 mansion. The rooms feature herringbone wood floors, diamond-pane windows, and soaring 11-inch ceilings, creating an atmosphere that feels both magical and timeless. With its charming, historic details and exceptionally friendly owners, staying here is like stepping into an enchanting, old-world retreat."
The price is NT$4,548
NT$5,687 total
includes taxes & fees
Nov 24 - Nov 25
Whistler's Inn Bed & Breakfast
Shaker Mill Inn
Exterior
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (399)
"This place is so comfortable and roomy. Perfect place for a quiet getaway. "
The price is NT$4,626
NT$5,075 total
includes taxes & fees
Nov 6 - Nov 7
Shaker Mill Inn
Inn at Pine Plains
Free daily continental breakfast
Inn at Pine Plains
3.5 star property
9.8 out of 10, Exceptional, (277)
"Ideal version of a New England inn. "
The price is NT$8,136
NT$9,122 total
includes taxes & fees
Nov 6 - Nov 7
Inn at Pine Plains
Inn at Silver Maple Farm
Aerial view
Inn at Silver Maple Farm
3.0 star property
9.8 out of 10, Exceptional, (77)
"A perfect place to enjoy fall colors. Generous and delicious breakfast."
The price is NT$5,073
NT$5,479 total
includes taxes & fees
Nov 26 - Nov 27
Inn at Silver Maple Farm
Wilder House Berkshires
Wilder House Berkshires Room 3 | Individually decorated, individually furnished, blackout drapes
Wilder House Berkshires
2.0 star property
9.8 out of 10, Exceptional, (9)
"Beautiful property, super clean, close to great Barrington, and has EV charging, which was a plus. Can’t wait to visit again. "
The price is NT$3,836
NT$4,285 total
includes taxes & fees
Nov 7 - Nov 8
Wilder House Berkshires
Changing Times Boutique Country Lodging
Family Cabin, Multiple Beds, Patio, Garden Area | Premium bedding, individually decorated, individually furnished, desk
Changing Times Boutique Country Lodging
3.5 star property
10.0 out of 10, Exceptional, (91)
"Incredible B&B experience. Our host Loretta was welcoming, attentive and a fantastic cook. Room was unique and comfortable. The optional breakfast was not to be missed. "
The price is NT$4,786
NT$5,169 total
includes taxes & fees
Nov 6 - Nov 7
Changing Times Boutique Country Lodging
Granville House
Interior detail
Granville House
3.0 star property
10.0 out of 10, Exceptional, (76)
"The surroundings were quiet and peaceful. The hosts were welcoming and friendly. Wonderful people "
The price is NT$6,381
NT$7,128 total
includes taxes & fees
Nov 10 - Nov 11
Granville House
33 Main
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main
4.0 star property
10.0 out of 10, Exceptional, (67)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
The price is NT$11,164
NT$12,470 total
includes taxes & fees
Nov 7 - Nov 8
33 Main
Jenny's Country Manor
30-inch TV with digital channels
Jenny's Country Manor
2.0 star property
7.6 out of 10, Good, (123)
"The manager was very amenable to changing our room due to a complaint about a problem we had. And was sincerely concerned. They have a very nice light breakfast on Saturday mornings. "
The price is NT$4,467
NT$5,008 total
includes taxes & fees
Nov 6 - Nov 7
Jenny's Country Manor
Brook Farm Inn
Front of property
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (147)
"Very charming inn. The staff was very friendly and helpful."
The price is NT$6,923
NT$7,733 total
includes taxes & fees
Nov 7 - Nov 8
Brook Farm Inn
Manor House Inn
Interior detail
Manor House Inn
3.0 star property
9.2 out of 10, Wonderful, (134)
"The woodwork and stained glass. "
The price is NT$11,603
NT$12,879 total
includes taxes & fees
Nov 8 - Nov 9
Manor House Inn
Devonfield Inn B&B
Front of property - evening/night
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (116)
"The Inn is very nice, however the room received was too small and was very limited for comfort. Breakfasts were great and the concert on Saturday was especially special. Would stay again if another room was available . "
The price is NT$8,908
NT$9,951 total
includes taxes & fees
Nov 12 - Nov 13
Devonfield Inn B&B
The Inn at Stockbridge
Exterior
The Inn at Stockbridge
4.0 star property
9.8 out of 10, Exceptional, (96)
"Well-run and elegant property. "
The Inn at Stockbridge
Eastgate Inn B&B
Porch
Eastgate Inn B&B
2.5 star property
9.2 out of 10, Wonderful, (68)
"Lovely Inn and Innkeeper. The room was clean and cozy. There was hot coffee and breakfast in the morning including homemade breads and fruit. We will be back! "
Eastgate Inn B&B
Tanglewood Suites
2 Bedrooms 1 Bath | Premium bedding, iron/ironing board, free WiFi, bed sheets
Tanglewood Suites
2.5 star property
8.0 out of 10, Very Good, (15)
"Portion of hosts home, separate and available for rent. Heating system not efficient and took some work to sort out how to keep all areas of the unit comfortably heated. Beds clean and comfortable. Overall cleanliness was good. Bath facilities are an addition to existing structure and sufficient, but could use some TLC. Host is eager to please and pleasant to interact with. Listing indicates free breakfast for all guests. However, upon arrival, we were advised there is no winter offering of...
The price is NT$6,987
NT$6,987 total
includes taxes & fees
Nov 6 - Nov 7
Tanglewood Suites
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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Other property types in Sheffield

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, Mount Everett State Reservation 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: The Cornell Inn, Lenox: 18.1 mi (29.1 km) from the heart of Sheffield. Enjoy the free full breakfast and unique décor. Lakehouse Inn: 14 rooms. 15.7 mi (25.2 km) from the downtown core. Enjoy the free full breakfast and deli. 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.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 Mount Everett State Reservation are some notable spots. You might put Magnolia Bluffs Casino and Ashley House 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.