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Compare 33 B&B in Sheffield with updated reviews, rates, and availability.

Blackberry River Inn
3.0 star property
9.4 out of 10, Exceptional, (33)
"Great and excellent. Breakfast is perfect. "
Blackberry River Inn
The Cornell Inn, Lenox
3.0 star property
8.8 out of 10, Excellent, (1002)
"Wonderful property, great staff and delicious made to order breakfast "
The price is AED 463
AED 538 total
includes taxes & fees
24 Jun - 25 Jun
The Cornell Inn, Lenox
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, (162)
"Excellent place to stay. Convenient, clean, beautiful views, wonderful breakfast and snacks. Highly recommend!"
The price is AED 551
AED 640 total
includes taxes & fees
19 Jun - 20 Jun
Lakehouse Inn
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Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, (327)
"This spot is very cozy and we really enjoyed our brief stay here. The owners are very friendly and make a delicious, home style breakfast complete with eggs from their chickens. It’s on a main road but we couldn’t hear the traffic and we slept well. The rooms aren’t over the top in size or luxury, but it was comfortable and the shared bathroom wasn’t an issue at all as it was right across the hall and we never had to wait for other patrons in order to use it. Would return and recommend!"
The price is AED 386
AED 444 total
includes taxes & fees
19 Jun - 20 Jun
Locust Tree Bed and Breakfast LLC
Inn at Pine Plains
3.5 star property
9.8 out of 10, Exceptional, (263)
"Nice comfortable convenient accommodations. Perfect. "
The price is AED 937
AED 1,051 total
includes taxes & fees
19 Jun - 20 Jun
Inn at Pine Plains
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (386)
"Wonderful place to stay in western Massachusetts."
The price is AED 830
AED 910 total
includes taxes & fees
25 Jun - 26 Jun
Shaker Mill Inn
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (138)
"This is a charming and very pleasant place to stay."
The price is AED 797
AED 890 total
includes taxes & fees
21 Jun - 22 Jun
Brook Farm Inn
Whistler's Inn Bed & Breakfast
3.5 star property
7.8 out of 10, Good, (435)
"My room was tiny but the Inn hostess was very accommodating/hospitable. The house was reminiscent of an English country BnB. Lots of stories have clearly played out in this old estate house. Right across street from lovely church and cemetery filled with pre-revolutionary war souls and a short walk up the hill from Lenox Main Street. "
The price is AED 585
AED 654 total
includes taxes & fees
19 Jun - 20 Jun
Whistler's Inn Bed & Breakfast
33 Main
4.0 star property
10.0 out of 10, Exceptional, (63)
"I love the fact that it only had eight rooms they had happy hour from 5 to 6 PM so we are able to meet other people at the hotel. I love the rooms and the cleanliness and especially the breakfast they were amazing and delicious!! I would recommend this hotel highly!"
The price is AED 1,502
AED 1,678 total
includes taxes & fees
19 Jun - 20 Jun
33 Main
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (356)
"Amazing place.."
The price is AED 1,469
AED 1,641 total
includes taxes & fees
19 Jun - 20 Jun
Chambery Inn
The Barrington
4.0 star property
9.6 out of 10, Exceptional, (99)
"As always, our stay at The Barrington was wonderful. The rooms are large, lovely and the bed comfortable. The service is great and everyone is so friendly and accommodating! The breakfast is delicious. We truly enjoy our stay, every time!"
The price is AED 1,194
AED 1,333 total
includes taxes & fees
19 Jun - 20 Jun
The Barrington
Jenny's Country Manor
2.0 star property
7.6 out of 10, Good, (116)
"Really nice room in a fairly run down looking hotel from the outside. But the room Is lovey, clean and spacious "
The price is AED 496
AED 556 total
includes taxes & fees
19 Jun - 20 Jun
Jenny's Country Manor
Changing Times Boutique Country Lodging
3.5 star property
10.0 out of 10, Exceptional, (84)
"It was comfortable"
The price is AED 551
AED 595 total
includes taxes & fees
19 Jun - 20 Jun
Changing Times Boutique Country Lodging
Manor House Inn
3.0 star property
9.2 out of 10, Wonderful, (128)
"Excellent bed and breakfast, room was clean and comfortable."
The price is AED 1,010
AED 1,101 total
includes taxes & fees
27 Jun - 28 Jun
Manor House Inn
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (106)
"The classic character of the Inn is so beautiful and adds to the whole experience!"
The price is AED 1,429
AED 1,596 total
includes taxes & fees
21 Jun - 22 Jun
Devonfield Inn B&B
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
9.2 out of 10, Wonderful, (101)
"The b&b was so beautiful and unique! The area was serene. The host was very sweet and accommodating."
The price is AED 1,685
AED 2,039 total
includes taxes & fees
19 Jun - 20 Jun
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Granville House
3.0 star property
10.0 out of 10, Exceptional, (70)
"Very nice hosts and lovely and inventive decor."
The price is AED 1,194
AED 1,333 total
includes taxes & fees
27 Jun - 28 Jun
Granville House
The Inn at Stockbridge
4.0 star property
9.6 out of 10, Exceptional, (94)
"Fantastic!"
The Inn at Stockbridge
Inn at Kenmore Hall
3.0 star property
10.0 out of 10, Exceptional, (25)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
Inn at Kenmore Hall
Tanglewood Suites
2.5 star property
8.0 out of 10, Very Good, (15)
"The property is so lovely and peaceful. I love the classic mid-century modern aesthetic. For visitors to the National Shrine of Divine Mercy, the Inn’s location couldn’t be more perfect with only a 5-minute walk to the Shrine. "
Tanglewood Suites
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See all available properties in Sheffield
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.

Other property types in Sheffield

Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (22)
"This home was "as advertised" - plenty of room. Nice neighborhood setting. Well stocked kitchen & nice outside area in the backyard / deck. We used it as a base camp for section hiking the appalachian trail."
The price is AED 797
AED 1,760 total
includes taxes & fees
19 Jun - 20 Jun
Cheerful 3-bedroom cottage with woodstove
Antique Farmhouse Totally Restored
10.0 out of 10, Exceptional, (80)
"We have 20 years experience renting homes for family gatherings and this is the most interesting and amazing property. Gardens galore, plenty of space to congregate or go off by yourself, fully appointed kitchen, and comfortable space. We were a party of ten and everyone loved the experience."
Antique Farmhouse Totally Restored
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
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 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.
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, Mount Everett State Reservation and Housatonic River are some notable spots. You might put Magnolia Bluffs Casino and Thom Reed UFO Monument Park 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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