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Check prices for these dates

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Apr 25 - Apr 27
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May 2 - May 4
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May 16 - May 18
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Jun 13 - Jun 15

Compare 30 B&B in Sheffield with updated reviews, rates, and availability.

The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Lovely, comfortable B&B with a nice feel. We plan to return."
The price is ￥17,571
￥25,171 total
includes taxes & fees
Apr 20 - Apr 21
The Cornell Inn, Lenox & The Berkshires
Lakehouse Inn
Porch

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (255)
"We had a great stay at The Lakehouse Inn. Upon arrival we were greeted with a beverage and brownies. Our room was lovely, the new gas fireplace was a bonus. And the breakfast was out of this world! Service was fantastic from everyone involved, especially our breakfast server Kathleen. We would definitely recommend a stay here."
Lakehouse Inn
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.6 out of 10, Exceptional, (99)
"So charming, friendly staff, perfectly comfortable. We had the best stay. "
The price is ￥23,578
￥27,115 total
includes taxes & fees
May 5 - May 6
Blackberry River Inn
Wilder House Berkshires
Wilder House Berkshires Room 3 | Premium bedding, individually decorated, individually furnished

Wilder House Berkshires

2.0 star property
9.6 out of 10, Exceptional, (20)
"Bert was great - he really tried to help after the Expedia website (and app) made it impossible for me to cancel my trip (my wife and I came down with Influenza A). There was little he could do as I had booked through Expedia. I ended up paying full price and am finding it impossible to communicate with Expedia..."
The price is ￥21,698
￥24,237 total
includes taxes & fees
Apr 27 - Apr 28
Wilder House Berkshires
Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (377)
"The host Heidi was friendly and fun to talk with at breakfast (I was travelling alone). She knows a lot about the area and history which was nice to hear. The house was quiet and clean and I'd stay here again."
The price is ￥14,891
￥17,125 total
includes taxes & fees
Apr 18 - Apr 19
Locust Tree Bed and Breakfast LLC
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (409)
"Beautiful room, very clean. breakfast was not what i was expecting, walk way from parking lot covered with ice and snow, very dangerous to walk, needs to be cleaned or at least put some salt on the ground. other then that everything was excellent. will stay again"
The price is ￥20,564
￥22,558 total
includes taxes & fees
Apr 20 - Apr 21
Shaker Mill Inn
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (363)
"Chamberry Inn was a nice, quiet, relaxing stay. Enjoyed every second of it. The staff were kind and helpful. Would definitely stay again if I was in the area."
The price is ￥34,035
￥38,018 total
includes taxes & fees
Apr 18 - Apr 19
Chambery Inn
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, (70)
"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 ￥55,636
￥62,145 total
includes taxes & fees
Apr 22 - Apr 23
33 Main
Inn at Pine Plains
Free daily continental breakfast

Inn at Pine Plains

3.5 star property
9.8 out of 10, Exceptional, (281)
"A charming inn with nice rooms upstairs and downstairs and a variety of cozy public rooms on the ground floor. Very nice, serve-yourself continental breakfast, although no hot food (at least not on our weekend). Well-located near the center of Pine Plains."
The price is ￥36,164
￥40,909 total
includes taxes & fees
Apr 20 - Apr 21
Inn at Pine Plains
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (151)
"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 ￥24,677
￥27,564 total
includes taxes & fees
Apr 18 - Apr 19
Brook Farm Inn
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (124)
"Very enjoyable comfortable stay"
The price is ￥35,313
￥39,444 total
includes taxes & fees
Apr 19 - Apr 20
Devonfield Inn B&B
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...
The price is ￥23,205
￥28,616 total
includes taxes & fees
May 1 - May 2
Whistler's Inn Bed & Breakfast
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, sun loungers

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 ￥60,181
￥72,801 total
includes taxes & fees
Apr 20 - Apr 21
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Jenny's Country Manor
Exterior

Jenny's Country Manor

2.0 star property
7.6 out of 10, Good, (126)
"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 ￥19,855
￥22,462 total
includes taxes & fees
Apr 20 - Apr 21
Jenny's Country Manor
Inn at Silver Maple Farm
Aerial view

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (84)
"Here’s the review translated into English: ⭐⭐⭐⭐⭐ (5 stars – if there were 8, we’d give 8!) We had an unforgettable stay at the Maple Farm Hotel! The accommodation is decorated with incredible attention to detail and taste – the warm wood, stylish furniture, and countless charming little touches create a beautiful, natural atmosphere. In the mornings, we were awakened by the cheerful chirping of birds, which was simply magical. We especially loved the cozy hours by the fireplace and the...
The price is ￥21,131
￥22,821 total
includes taxes & fees
Apr 20 - Apr 21
Inn at Silver Maple Farm
Manor House Inn
Garden

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, (98)
"We we were in the Out of Africa room, set apart in a complex of 4 suites in a unit apart from the Inn itself. The room was uniquely created to feel like an escape to Africa, and heated by a lovely gas fireplace. The breakfast both mornings, delicious. A perfect getaway!"
The Inn at Stockbridge
Granville House
Interior detail

Granville House

3.0 star property
10.0 out of 10, Exceptional, (82)
"Phenomenal hospitality, eclectic decor, luxurious sleep - we have been raving about our stay and will definitely be back!"
The price is ￥28,222
￥31,524 total
includes taxes & fees
Apr 20 - Apr 21
Granville House
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 ￥31,059
￥31,059 total
includes taxes & fees
Apr 18 - Apr 19
Tanglewood Suites
Inn at Kenmore Hall
Lobby

Inn at Kenmore Hall

3.0 star property
10.0 out of 10, Exceptional, (27)
"A wonderful experience……….breakfast overlooking the property, the beautiful flowers grown by the innkeepers, decorated to perfection, with owners there to make your stay as comfortable as possible! "
The price is ￥60,274
￥66,121 total
includes taxes & fees
Apr 20 - Apr 21
Inn at Kenmore Hall
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

Guesthouse Cabin vacation rentals in Berkshire County
Exterior

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (5)
"Two very comfortable nights. Cabin is well appointed. Great kitchen and outdoor space. Tremendous views, amazing star gazing. Very private. "
The price is ￥71,619
￥123,087 total
includes taxes & fees
Apr 21 - Apr 22
Guesthouse Cabin vacation rentals in Berkshire County
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
Deluxe Queen Room with 2 Queen Beds
1 bedroom, WiFi, bed sheets

Deluxe Queen Room with 2 Queen Beds

2.0 star property
The price is ￥15,458
￥20,434 total
includes taxes & fees
Apr 21 - Apr 22
Deluxe Queen Room with 2 Queen Beds
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: Wilder House Berkshires: 5 rooms. 0.3 mi (0.5 km) from the heart of Sheffield. Enjoy the free cooked breakfast and unique décor. The Cornell Inn, Lenox & The Berkshires: 18.1 mi (29.1 km) from the downtown core. Enjoy the free full breakfast and unique décor. Locust Tree Bed and Breakfast LLC: 7 rooms. Situated 6.8 mi (11 km) from the heart of Sheffield. Blackberry River Inn: 14 rooms. 9.2 mi (14.9 km) from the heart of downtown. Enjoy the free cooked breakfast and outdoor pool. Chambery Inn: 9 rooms. Located 14.7 mi (23.7 km) from the core of Sheffield. Enjoy the private yard and deli.
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.