Search B&B in Sheffield

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation
Library
Blackberry River Inn
3.0 star property
9.6 out of 10, Exceptional, (26)
"Cozy, comfortable, feels like you are staying at someone’s home that you love, but, lol with privacy! Breakfast is fabulous and eggs are made to order!"
The price is HK$1,416
per night
29 May - 30 May
Blackberry River Inn
Porch
The Cornell Inn, Lenox
3.0 star property
8.6 out of 10, Excellent, (1000)
"It was a great place to stay for the night. "
The price is HK$951
per night
23 May - 24 May
The Cornell Inn, Lenox
Aerial view
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, (152)
"The Lakehouse Inn is really cute, right on a lake with wonderful waterfront spaces. The bathroom situation is more European--toilet and shower in the bathroom, sink outside. There was no tub, not a problem for me but good to be aware of. The morning breakfast was delicious! I was greeted with a white wine sangria. It's conveniently located for roaming around Stockbridge, Great Barrington, etc. Close to the Norman Rockwell museum, Hancock Shaker Village, Edith Wharton estate. Would absolutely...
The price is HK$1,053
per night
27 May - 28 May
Lakehouse Inn
Save an average of 15% on thousands of hotels when you're signed in
Miscellaneous
Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, (322)
"Great B&B … everything is easy, clean, friendly owners, great breakfast! "
The price is HK$819
per night
23 May - 24 May
Locust Tree Bed and Breakfast LLC
Garden
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (383)
"We felt like the place was all our own. From the en suite breakfast to our private deck, we felt right at home immediately and had a lovely weekend stay. The surrounding mountains and quaint New England mill town were off-the-charts charming. Our inn keepers were just a phone call away when we had a request. Everything was immaculately clean and extremely well maintained (I'm a handyman at heart). I can't wait for you to stay here- it's minutes away from Stockbridge, Lennox, Great...
The price is HK$1,069
per night
29 May - 30 May
Shaker Mill Inn
Free daily continental breakfast
Inn at Pine Plains
3.5 star property
9.8 out of 10, Exceptional, (258)
"Lovely overnight stay. Room was beautiful and very comfortable. Breakfast consisted of a nice selection of homemade bread and muffins - and humus (so yummy). Staff is super friendly and made sure to engage with everyone. Would definitely stay here again. "
The price is HK$1,755
per night
23 May - 24 May
Inn at Pine Plains
Front of property
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (135)
"This is a charming and very pleasant place to stay."
The price is HK$1,107
per night
23 May - 24 May
Brook Farm Inn
Property grounds
Whistler's Inn Bed & Breakfast
3.5 star property
7.6 out of 10, Good, (432)
"Terrific host. Very welcoming. "
The price is HK$1,693
per night
20 Jun - 21 Jun
Whistler's Inn Bed & Breakfast
Exterior
The Inn at Stockbridge
4.0 star property
9.6 out of 10, Exceptional, (92)
"Great B&B with everything you need especially for a quick getaway to vist Stockbridge & Great Barrington Massachusetts. The new owners have added new touches to this Inn and the pride of ownership shows. Highly recommended 👌 "
The Inn at Stockbridge
Front of property – evening/night
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 HK$2,099
per night
28 May - 29 May
Devonfield Inn B&B
Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main
4.0 star property
10.0 out of 10, Exceptional, (62)
"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 HK$3,018
per night
29 May - 30 May
33 Main
Front of property
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (356)
"Amazing place.."
The price is HK$1,867
per night
28 May - 29 May
Chambery Inn
Premium bedding, individually decorated, desk, iron/ironing board
The Barrington
4.0 star property
9.6 out of 10, Exceptional, (98)
"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 HK$2,535
per night
27 May - 28 May
The Barrington
Interior detail
Granville House
4.0 star property
10.0 out of 10, Exceptional, (70)
"Very nice hosts and lovely and inventive decor."
The price is HK$1,560
per night
23 May - 24 May
Granville House
Premium bedding, individually decorated, individually furnished, desk
Changing Times Boutique Country Lodging
3.5 star property
10.0 out of 10, Exceptional, (84)
"It was comfortable"
The price is HK$1,170
per night
3 Jun - 4 Jun
Changing Times Boutique Country Lodging
Interior detail
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 HK$2,101
per night
26 May - 27 May
Manor House Inn
30-inch TV with digital channels
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 HK$1,053
per night
23 May - 24 May
Jenny's Country Manor
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
Business centre
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 HK$2,940
per night
23 May - 24 May
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Exterior
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
9.8 out of 10, Exceptional, (10)
"We would return to the inn again. Bob was wonderful and very, very accommodating:-)"
The price is HK$2,332
per night
23 May - 24 May
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
Don't see what you're looking for?
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

Exterior
Antique Farmhouse Totally Restored
10.0 out of 10, Exceptional, (79)
"There were 6 adults and 2 infants in our party, we were in town for our 25 year high school reunion. The house was incredible and the host went above and beyond to make sure we were well taken care of. This place is a hidden gem and deserves all of the praise."
Antique Farmhouse Totally Restored
Property grounds
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (22)
"We rented for the winter to use on the weekends. Sabrina was very responsive and thoughtful throughout. The house is incredibly well stocked and thoughtfully organized. Two seating areas downstairs made it easy for our family of four to spread out, even when we had guests. Kitchen is well laid out, mattresses are very comfortable, and the surrounding area is quiet. We would definitely go back."
The price is HK$1,536
per night
27 May - 28 May
Cheerful 3-bedroom cottage with woodstove
Interior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (184)
"My husband and I had a very peaceful and relaxing long weekend at this lake house! It was very clean and has everything you need. We spent the majority of our time on the wonderful screened-in porch. The location was great and there was a little store/restaurant only a couple minutes walk up the street that was convenient and the food was really good! Overall, a great place to stay!"
Peace and quiet on the lake
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.

Sheffield B&B information

Number of reviews
3,114
Accommodation
34 B&B
Lowest Price
HK$819
Highest Price
HK$3,018

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. Blackberry River Inn: 14 rooms. 9.2 mi (14.9 km) from the city centre. Enjoy the free cooked breakfast and outdoor pool. Lakehouse Inn: 14 rooms. Situated 15.7 mi (25.2 km) from the heart of Sheffield. Enjoy the free full breakfast and snack bar/deli. 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, Mount Everett State Reservation and Housatonic River are some notable spots. You should 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?
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.

Recent Hotel Reviews in Sheffield
Expedia verified reviews