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

Blackberry River Inn
Breakfast meal
Blackberry River Inn
3.0 star property
9.4 out of 10, Exceptional, (31)
"Great and excellent. Breakfast is perfect. "
The price is SAR 681
SAR 765 total
includes taxes & fees
16 Jum. II - 17 Jum. II
Blackberry River Inn
The Cornell Inn, Lenox
Exterior
The Cornell Inn, Lenox
3.0 star property
8.8 out of 10, Excellent, (1002)
"The staff was very friendly and the breakfast was delicious. The outdoor areas were beautiful. The room was beautifully designed"
The price is SAR 439
SAR 510 total
includes taxes & fees
4 Jum. II - 5 Jum. II
The Cornell Inn, Lenox
Lakehouse Inn
Lake
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, (155)
"They greeted us as soon as we checked in with apple cider and brownies. The room was super cute. Breakfast was delicious. The only negative was it could be noisy when people are walking in hallway. We will definitely stay again. "
The price is SAR 495
SAR 575 total
includes taxes & fees
4 Jum. II - 5 Jum. II
Lakehouse Inn
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Inn at Pine Plains
Breakfast area
Inn at Pine Plains
3.5 star property
9.8 out of 10, Exceptional, (259)
"What a perfect little B and B! We stayed in the the Tamarack room, which was equipped with a separate living room and kitchen area. There were a few complimentary snacks and beverages along with a Keurig. Everything exceeded our expectations."
The price is SAR 956
SAR 1,073 total
includes taxes & fees
4 Jum. II - 5 Jum. II
Inn at Pine Plains
Locust Tree Bed and Breakfast LLC
Miscellaneous
Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, (325)
"Host was excellent and helpful. Location is quiet and close to nearby towns for activities. "
The price is SAR 394
SAR 453 total
includes taxes & fees
4 Jum. II - 5 Jum. II
Locust Tree Bed and Breakfast LLC
Brook Farm Inn
Front of property
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (136)
"Wonderful hospitality. Amazing breakfast. Will be back!!"
The price is SAR 754
SAR 842 total
includes taxes & fees
4 Jum. II - 5 Jum. II
Brook Farm Inn
Shaker Mill Inn
Garden
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (386)
"Quaint "
The price is SAR 493
SAR 540 total
includes taxes & fees
5 Jum. II - 6 Jum. II
Shaker Mill Inn
Chambery Inn
Front of property
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (356)
"Amazing place.."
The price is SAR 934
SAR 1,043 total
includes taxes & fees
4 Jum. II - 5 Jum. II
Chambery Inn
The Barrington
View from room
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 SAR 1,219
SAR 1,362 total
includes taxes & fees
4 Jum. II - 5 Jum. II
The Barrington
33 Main
Room
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 SAR 1,452
SAR 1,621 total
includes taxes & fees
5 Jum. II - 6 Jum. II
33 Main
The Inn at Stockbridge
Exterior
The Inn at Stockbridge
4.0 star property
9.6 out of 10, Exceptional, (94)
"Fantastic!"
The Inn at Stockbridge
Whistler's Inn Bed & Breakfast
Interior
Whistler's Inn Bed & Breakfast
3.5 star property
7.6 out of 10, Good, (433)
"Gorgeous loved large home where you will feel at home. Lots of antiques, books. Grand piano. Hosts very welcoming. No air conditioning. Hot showers once hot water heater turned on. First night unfortunately cool shower. Dog friendly. Breakfast choice fine. So near to Lennox (easy walk downhill) and close to Tanglewood. Really comfortable beds. This is an old house built in 1867 and there are many ongoing minor repairs to do with walls. Highly recommend and looking forward to returning. "
The price is SAR 510
SAR 570 total
includes taxes & fees
17 Jum. II - 18 Jum. II
Whistler's Inn Bed & Breakfast
Manor House Inn
Restaurant
Manor House Inn
3.0 star property
9.2 out of 10, Wonderful, (127)
"Exceptional in all ways. Gourmet breakfasts, beautiful house and grounds, elegant bedroom, wonderful staff. "
The price is SAR 1,031
SAR 1,124 total
includes taxes & fees
6 Jum. II - 7 Jum. II
Manor House Inn
Granville House
Room
Granville House
3.0 star property
10.0 out of 10, Exceptional, (70)
"Very nice hosts and lovely and inventive decor."
The price is SAR 1,031
SAR 1,152 total
includes taxes & fees
4 Jum. II - 5 Jum. II
Granville House
Devonfield Inn B&B
Room
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 SAR 1,384
SAR 1,546 total
includes taxes & fees
5 Jum. II - 6 Jum. II
Devonfield Inn B&B
Changing Times Boutique Country Lodging
Front of property
Changing Times Boutique Country Lodging
3.5 star property
10.0 out of 10, Exceptional, (84)
"It was comfortable"
The price is SAR 563
SAR 608 total
includes taxes & fees
4 Jum. II - 5 Jum. II
Changing Times Boutique Country Lodging
Jenny's Country Manor
Exterior
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 SAR 506
SAR 568 total
includes taxes & fees
4 Jum. II - 5 Jum. II
Jenny's Country Manor
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
View from room
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 SAR 1,721
SAR 2,082 total
includes taxes & fees
4 Jum. II - 5 Jum. II
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Inn at Kenmore Hall
Front of property
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
Property grounds
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
great kitchen for cooking in
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 SAR 814
SAR 1,797 total
includes taxes & fees
19 Jum. II - 20 Jum. II
Cheerful 3-bedroom cottage with woodstove
Antique Farmhouse Totally Restored
Sunrise lights up the front of the house. Moon sets over the mountain.
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
Sandisfield Vacation Rental | 4BR | 3BA | 1,978 Sq Ft | Stairs Required
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, Thom Reed UFO Monument Park and Mount Everett State Reservation 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, Housatonic River and Thom Reed UFO Monument Park 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.

Recent reviews of Sheffield hotels
Expedia verified reviews

Quality Inn

Quality Inn

5/5 Excellent
Birthday Trip
"Our stay was excellent. I greatly appreciated the refrigerator and microwave in the room. The proximity to everything in Lee was marvelous."
A verified traveler stayed at Quality Inn
Posted 15 hours ago
Quality Inn