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Check prices for these dates

Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar
In one month
14 Mar - 16 Mar
In two months
11 Apr - 13 Apr

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

The Cornell Inn, Lenox
Exterior

The Cornell Inn, Lenox

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Great Inn, first time at a Bed and Breakfast and it was more than expected. Would come back. "
The price is AED 448
AED 526 total
includes taxes & fees
19 Feb - 20 Feb
The Cornell Inn, Lenox
Lakehouse Inn
Lake

Lakehouse Inn

4.0 star property
9.8 out of 10, Exceptional, (245)
"We loved the history of the hotel and how well they preserved many features of the property. Loved the suite and view of the lake. Everyone that works there was very kind and attentive."
The price is AED 463
AED 543 total
includes taxes & fees
21 Feb - 22 Feb
Lakehouse 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 AED 698
AED 780 total
includes taxes & fees
18 Feb - 19 Feb
Chambery Inn
Blackberry River Inn
Breakfast meal

Blackberry River Inn

3.0 star property
9.6 out of 10, Exceptional, (97)
"We spent one night and loved the place. It's a beautiful, stately old inn. Our room was nicely appointed and very comfortable. Lucas made us feel at home, and cooked a marvelous breakfast. We'd highly recommend."
The price is AED 604
AED 694 total
includes taxes & fees
18 Feb - 19 Feb
Blackberry River Inn
Wilder House Berkshires
Breakfast meal

Wilder House Berkshires

2.0 star property
10.0 out of 10, Exceptional, (16)
"Room was very cozy and beautiful. Brad was very helpful and pleasant. The breakfast was delicious. We had a great getaway. Thank you. "
The price is AED 493
AED 551 total
includes taxes & fees
23 Feb - 24 Feb
Wilder House Berkshires
Tanglewood Suites
Property grounds

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 AED 804
AED 804 total
includes taxes & fees
18 Feb - 19 Feb
Tanglewood Suites
Inn at Pine Plains
Breakfast area

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 AED 937
AED 1,060 total
includes taxes & fees
18 Feb - 19 Feb
Inn at Pine Plains
33 Main
Room

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 AED 1,410
AED 1,576 total
includes taxes & fees
24 Feb - 25 Feb
33 Main
Granville House
Room

Granville House

3.0 star property
10.0 out of 10, Exceptional, (81)
"Lovely place with lovely hosts. The property is eclectic and wonderfully decorated with a very cool common area. Highly recommend "
The price is AED 918
AED 1,026 total
includes taxes & fees
27 Feb - 28 Feb
Granville House
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (407)
"Beautiful inn. It was nice and quiet, exactly what I needed. "
The price is AED 386
AED 423 total
includes taxes & fees
18 Feb - 19 Feb
Shaker Mill Inn
Devonfield Inn B&B
Room

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (122)
"Beautiful property, great service "
The price is AED 915
AED 1,022 total
includes taxes & fees
24 Feb - 25 Feb
Devonfield Inn B&B
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 AED 1,700
AED 1,899 total
includes taxes & fees
18 Feb - 19 Feb
Brook Farm Inn
Locust Tree Bed and Breakfast LLC
Exterior

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (375)
"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 AED 386
AED 444 total
includes taxes & fees
23 Feb - 24 Feb
Locust Tree Bed and Breakfast LLC
Inn at Silver Maple Farm
Front of property

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (81)
"Everything "
The price is AED 547
AED 591 total
includes taxes & fees
2 Mar - 3 Mar
Inn at Silver Maple Farm
Manor House Inn
Restaurant

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 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, (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 AED 1,559
AED 1,886 total
includes taxes & fees
18 Feb - 19 Feb
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, (125)
"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 AED 514
AED 582 total
includes taxes & fees
18 Feb - 19 Feb
Jenny's Country Manor
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
Inn at Kenmore Hall
Front of property

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 AED 1,561
AED 1,713 total
includes taxes & fees
18 Feb - 19 Feb
Inn at Kenmore Hall
Changing Times Boutique Country Lodging
Front of property

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 AED 551
AED 595 total
includes taxes & fees
2 Mar - 3 Mar
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

Guesthouse Cabin vacation rentals in Berkshire County
Property grounds

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 AED 1,855
AED 3,188 total
includes taxes & fees
18 Feb - 19 Feb
Guesthouse Cabin vacation rentals in Berkshire County
Antique Farmhouse Totally Restored
Sunrise lights up the front of the house. Moon sets over the mountain.

Antique Farmhouse Totally Restored

9.8 out of 10, Exceptional, (85)
"Place is great. Has a old farmhouse feel with an update. Lots of spots within the house for people to hang out. We did a family birthday get together and had a great time. "
Antique Farmhouse Totally Restored
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
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: 18.1 mi (29.1 km) from the downtown core. Enjoy the free full breakfast and unique décor. Lakehouse Inn: 14 rooms. Situated 15.7 mi (25.2 km) from the heart of Sheffield. Enjoy the free full breakfast and deli. Chambery Inn: 9 rooms. 14.7 mi (23.7 km) from the heart of downtown. Enjoy the private yard and deli. Blackberry River Inn: 14 rooms. Located 9.2 mi (14.9 km) from the core of Sheffield. Enjoy the free cooked breakfast and outdoor pool.
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 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.