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

The Cornell Inn, Lenox
Porch

The Cornell Inn, Lenox

3.0 star property
9.0 out of 10, Wonderful, (1000)
"the staff was great. rooms where clean there is a bar on site & a bottle of red wine complimentary in the room. a lot in the area unfortunately it was too cold to enjoy a lot of of it"
The price is ￥19,176
￥22,490 total
includes taxes & fees
Jan 13 - Jan 14, 2025
The Cornell Inn, Lenox
Lakehouse Inn
Aerial view

Lakehouse Inn

4.0 star property
9.8 out of 10, Exceptional, (233)
"We really enjoyed our stay. The breakfast was really good and the added touch of a welcome drink was really fun and made our stay feel special. We would like to come back again. "
The price is ￥19,695
￥23,099 total
includes taxes & fees
Dec 29 - Dec 30
Lakehouse Inn
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.6 out of 10, Exceptional, (95)
"Very clean. The host was friendly and attentive. Great complimentary breakfast. Clean,quiet and very comfortable. "
The price is ￥24,501
￥28,177 total
includes taxes & fees
Jan 8 - Jan 9, 2025
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, (373)
"Very pretty setting and house. Comfortable bed. Nice view Would have liked bottled water available in the room. Breakfast was nice."
The price is ￥16,413
￥18,875 total
includes taxes & fees
Dec 30 - Dec 31
Locust Tree Bed and Breakfast LLC
Wilder House Berkshires
Wilder House Berkshires Room 3 | Premium bedding, individually decorated, individually furnished

Wilder House Berkshires

2.0 star property
9.8 out of 10, Exceptional, (10)
"Great place, very clean, hospitable and designed with impeccable taste. "
The price is ￥21,922
￥24,487 total
includes taxes & fees
Jan 2 - Jan 3, 2025
Wilder House Berkshires
Granville House
Interior detail

Granville House

3.0 star property
10.0 out of 10, Exceptional, (78)
"Wonderful stay. Charming inn with a virtual library of books for every interest. Terrific breakfast. Will definitely return."
The price is ￥31,436
￥35,114 total
includes taxes & fees
Dec 26 - Dec 27
Granville House
Inn at Pine Plains
Free daily continental breakfast

Inn at Pine Plains

3.5 star property
9.8 out of 10, Exceptional, (278)
"Ideal version of a New England inn. "
The price is ￥39,859
￥44,692 total
includes taxes & fees
Dec 31 - Jan 1, 2025
Inn at Pine Plains
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (361)
"Everything was amazing. It was truly an experience. "
The price is ￥29,697
￥33,172 total
includes taxes & fees
Dec 30 - Dec 31
Chambery Inn
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (404)
"Quaint "
The price is ￥16,413
￥18,004 total
includes taxes & fees
Jan 8 - Jan 9, 2025
Shaker Mill Inn
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (119)
"Great location "
The price is ￥46,997
￥52,495 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Devonfield Inn B&B
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, (69)
"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 ￥57,214
￥63,908 total
includes taxes & fees
Jan 20 - Jan 21, 2025
33 Main
Inn at Silver Maple Farm
Aerial view

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (80)
"Everything "
The price is ￥23,290
￥25,153 total
includes taxes & fees
Jan 12 - Jan 13, 2025
Inn at Silver Maple Farm
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 ￥34,232
￥34,232 total
includes taxes & fees
Dec 26 - Dec 27
Tanglewood Suites
Manor House Inn
Interior detail

Manor House Inn

3.0 star property
9.2 out of 10, Wonderful, (135)
"A charming old manor from the Gilded Age, thoughtfully updated and modernized without losing the soul of the original home. Incredibly comfortable rooms, inviting common spaces, excellent breakfast, beautiful grounds, and friendly staff. We especially enjoyed the fireplace in our room. Perfect for a romantic getaway, we look forward to visiting again in the future."
Manor House Inn
The Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (97)
"Very enjoyable stat."
The Inn at Stockbridge
Jenny's Country Manor
Miscellaneous

Jenny's Country Manor

2.0 star property
7.6 out of 10, Good, (124)
"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 ￥21,883
￥24,537 total
includes taxes & fees
Dec 31 - Jan 1, 2025
Jenny's Country Manor
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (149)
"Loves that they had en EV charger for me to charge while we were “home”. Beautiful location and house. Welcoming hospitality that was very refreshing. Thank you. "
The price is ￥28,764
￥32,129 total
includes taxes & fees
Jan 4 - Jan 5, 2025
Brook Farm Inn
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (471)
"I liked that it is an older style bed and breakfast place. You could say "classy" or "vintage". It reminded me of places where I would visit with family when I was a child. I received a personal welcome and orientation to the property. Breakfast was nice and cooked options were available for me to choose. Another guest in the dining room at breakfast was also enjoying the visit and it was natural to strike up a conversation and get to know each other. It was a more personal kind of stay than...
Whistler's Inn Bed & Breakfast
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business center

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
9.2 out of 10, Wonderful, (105)
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer most questions"
The price is ￥66,330
￥80,239 total
includes taxes & fees
Jan 8 - Jan 9, 2025
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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, (93)
"The stay was great. The host baked delicious muffins for breakfast and everything was clean "
The price is ￥23,577
￥25,463 total
includes taxes & fees
Jan 4 - Jan 5, 2025
Changing Times Boutique Country Lodging
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

Antique Farmhouse Totally Restored
Exterior

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (83)
"I'd describe the house as elegantly eclectic. The owner is clearly a collector of interesting items which they arrange in a way that enhance (rather than potentially clutter) the interior. The kitchen and living spaces are open and easy to mingle around. The four bedrooms and three bathrooms easily and comfortably accommodated two couples and two singles. Our stay could not have been better! "
Antique Farmhouse Totally Restored
Cheerful 3-bedroom cottage with woodstove
Property grounds

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (33)
"We stayed at this home about the same time last year and we were so happy with everything about it, we jumped at the opportunity to stay there again. The house has absolutely everything you'd need and is close to Canaan, CT and Great Barrington, MA and everything the Bershires have to offer. Sabrina is a great host and responded within minutes to any questions I had. We HIGHLY recommend this home."
The price is ￥37,045
￥79,267 total
includes taxes & fees
Jan 8 - Jan 9, 2025
Cheerful 3-bedroom cottage with woodstove
Peace and quiet on the lake
Interior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (200)
"My family and I really enjoyed our stay at the lake. My kids enjoyed playing outside in the snow. We had such a quality family time playing board games, watching movies and drinking hot cocoa. Justin was such a great host and really helpful when needed. We’re definitely coming back!"
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.

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 Three Mile Pond Wildlife Management Area 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.