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The Cornell Inn, Lenox
Porch
The Cornell Inn, Lenox
3.0 star property
8.8 out of 10, Excellent, (1001)
"The staff are charming and attentive. Although our room was small, the bed was super luxurious, the room was quiet and the bathroom was well-appointed. There's a lot of common space to lounge around and the Kennedy Park is just a short walk up the road. We were there in a shoulder season (November) but the outside looks like it would be really charming maybe from May through Spetember - pond and lots of places to sit and enjoy."
The price is HK$948
HK$1,112 total
includes taxes & fees
11 Nov - 12 Nov
The Cornell Inn, Lenox
Lakehouse Inn
Aerial view
Lakehouse Inn
4.0 star property
9.8 out of 10, Exceptional, (224)
"Great place. "
The price is HK$972
HK$1,140 total
includes taxes & fees
7 Nov - 8 Nov
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 HK$1,340
HK$1,541 total
includes taxes & fees
6 Nov - 7 Nov
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 HK$816
HK$939 total
includes taxes & fees
6 Nov - 7 Nov
Locust Tree Bed and Breakfast LLC
Chambery Inn
Front of property
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (359)
"Absolutely charming Inn. Will be returning as soon as possible!!! Lovely people and great customer service. Highly recommend!!!"
The price is HK$1,477
HK$1,649 total
includes taxes & fees
6 Nov - 7 Nov
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 HK$1,108
HK$1,385 total
includes taxes & fees
19 Nov - 20 Nov
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 HK$1,127
HK$1,236 total
includes taxes & fees
6 Nov - 7 Nov
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 HK$1,982
HK$2,222 total
includes taxes & fees
6 Nov - 7 Nov
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 HK$1,236
HK$1,335 total
includes taxes & fees
24 Nov - 25 Nov
Inn at Silver Maple Farm
Wilder House Berkshires
Individually decorated, individually furnished, blackout curtains
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 HK$1,029
HK$1,150 total
includes taxes & fees
7 Nov - 8 Nov
Wilder House Berkshires
Changing Times Boutique Country Lodging
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 HK$1,166
HK$1,259 total
includes taxes & fees
7 Nov - 8 Nov
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 HK$1,555
HK$1,736 total
includes taxes & fees
11 Nov - 12 Nov
Granville House
33 Main
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 HK$2,720
HK$3,038 total
includes taxes & fees
25 Nov - 26 Nov
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 HK$1,088
HK$1,220 total
includes taxes & fees
7 Nov - 8 Nov
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 HK$1,687
HK$1,884 total
includes taxes & fees
11 Nov - 12 Nov
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 HK$2,828
HK$3,139 total
includes taxes & fees
9 Nov - 10 Nov
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 HK$2,170
HK$2,424 total
includes taxes & fees
12 Nov - 13 Nov
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
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 HK$1,702
HK$1,702 total
includes taxes & fees
9 Nov - 10 Nov
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

Cheerful 3-bedroom cottage with woodstove
Property grounds
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (29)
"Sabrina saw to everything. The house even came equipped with a spice drawer, games like badminton equipment, a kid’s bedroom with games and books, and nice touches like vases of flowers. Our family was amazed and impressed. The outdoor area in the front (and back) was big enough for our grandchildren to play badminton. We very highly recommend this place!"
The price is HK$1,842
HK$3,924 total
includes taxes & fees
6 Nov - 7 Nov
Cheerful 3-bedroom cottage with woodstove
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Exterior
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (208)
"The Cabin Had All The Amenities You Would Need and With A Quiet and Serene Area. For Me It Was Relaxing Stay!"
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Pristine Home In Becket Woods
Fridge, microwave, oven, stovetop
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods
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.

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, 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 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: The Cornell Inn, Lenox: 18.1 mi (29.1 km) from the heart of Sheffield. Enjoy the free full breakfast and unique decor. Lakehouse Inn: 14 rooms. 15.7 mi (25.2 km) from the city centre. Enjoy the free full breakfast and snack bar/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 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 Mount Everett State Reservation are some notable spots. You should 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?
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.