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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
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Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

B&B in Sheffield

The Cornell Inn, Lenox & The Berkshires
Traditional two-story house with a welcoming porch and balcony, set amidst snow-covered trees.

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1003)
"Lovely place. Excellent staff, Wonderful breakfast."
The price is ￥18,759
￥26,697 total
includes taxes & fees
Sep 3 - Sep 4
The Cornell Inn, Lenox & The Berkshires
Blackberry River Inn
Cozy living room with a traditional fireplace, armchairs, and a sofa, perfect for relaxing.

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (122)
"We had a vey clean room with a comfortable bed The breakfast was awesome as was the entire staff. Enjoyed our stay"
The price is ￥24,146
￥27,768 total
includes taxes & fees
Sep 2 - Sep 3
Blackberry River Inn
Locust Tree Bed and Breakfast LLC
Relax on the covered porch with two comfortable rocking chairs and lush green surroundings.

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (397)
"Nice property! a little dated but overall great for 1 night"
The price is ￥15,427
￥17,741 total
includes taxes & fees
Aug 6 - Aug 7
Locust Tree Bed and Breakfast LLC
Shaker Mill Inn
Step into the charming Shaker Mill Inn, surrounded by lush greenery and a beautiful garden.

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (418)
"Very cute and clean room. After driving all day we were so happy to see all muffins, scones, yogurt, cereal, oatmeal, strawberries, milk, OJ, hot chocolate and coffee already in the room for breakfast the next day. We had a great stay, thank you!"
The price is ￥28,796
￥31,589 total
includes taxes & fees
Aug 12 - Aug 13
Shaker Mill Inn
Lakehouse Inn
Relax on the deck with a glass of wine, taking in the serene views of the surrounding water and lush landscape.

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (276)
"Great Views & Hospitality"
Lakehouse Inn
Inn at Pine Plains
Enjoy a warm breakfast in this cozy dining area with a brick fireplace, surrounded by a charming table setting.

Inn at Pine Plains

3.5 star property
9.8 out of 10, Exceptional, (288)
"Beautiful place. Accomadating staff. A lovely place to stay"
Inn at Pine Plains
Tanglewood Suites
Relax in this serene bedroom with a large bed, two chairs, and a small table, surrounded by lush views.

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. "
The price is ￥39,521
￥39,521 total
includes taxes & fees
Aug 12 - Aug 13
Tanglewood Suites
Inn at Silver Maple Farm
Set amidst lush greenery, this multi-story property features distinct buildings with gabled and flat roofs.

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (91)
"What a wonderful one-night stay on the July 4th weekend. It’s a beautiful, comfortable inn with lovely hosts. Also in a great location, set back from a fairly busy country road with several good food options nearby, and charming villages and towns to tour. Highly recommend. "
The price is ￥30,706
￥34,391 total
includes taxes & fees
Sep 3 - Sep 4
Inn at Silver Maple Farm
Wilder House Berkshires
Cozy retreat with a large bed, bedside tables, and a chandelier.

Wilder House Berkshires

2.0 star property
9.6 out of 10, Exceptional, (28)
"Always perfect! "
The price is ￥26,679
￥29,800 total
includes taxes & fees
Aug 18 - Aug 19
Wilder House Berkshires
Chambery Inn
Chambery Inn features a traditional two-story building with a pitched roof and multiple windows.

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (368)
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
Chambery Inn
Whistler's Inn Bed & Breakfast
Stroll through the beautifully manicured lawn and discover a vibrant garden filled with lush purple flowering bushes.

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (478)
"Nice quaint out of the ordinary vacation experience. "
The price is ￥25,110
￥28,047 total
includes taxes & fees
Aug 13 - Aug 14
Whistler's Inn Bed & Breakfast
Changing Times Boutique Country Lodging
Guests can enjoy a comfortable seating area on the covered porch.

Changing Times Boutique Country Lodging

3.5 star property
10.0 out of 10, Exceptional, (102)
"The b and b is charming and comfortable. Loretta was extremely welcoming and accommodating."
The price is ￥22,110
￥23,879 total
includes taxes & fees
Aug 6 - Aug 7
Changing Times Boutique Country Lodging
Brook Farm Inn
Relax in this inviting room with a comfortable bed, fireplace, and thoughtful amenities.

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (155)
"Maureen and her lovely staff operate a first class B&B. Thoughtful amenities and conveniences, clean and comfortable. Amazing home cooked breakfast, both plentiful and delicious. Thank you"
The price is ￥35,588
￥39,752 total
includes taxes & fees
Sep 3 - Sep 4
Brook Farm Inn
33 Main
Features a sleek glass-enclosed shower, vanity with sink and mirror, toilet, and bidet.

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! "
33 Main
Jenny's Country Manor
Stunning two-story house with a charming porch and symmetrical facade, featuring a central entrance and two garage doors.

Jenny's Country Manor

2.0 star property
7.6 out of 10, Good, (130)
"The paint job could be redone and the stair are a bit hazardous. The bath facilities could be improved."
The price is ￥20,569
￥23,269 total
includes taxes & fees
Aug 10 - Aug 11
Jenny's Country Manor
Manor House Inn
Classic elegance abounds in this traditional space, featuring a grand staircase and ornate grandfather clock.

Manor House Inn

3.0 star property
9.2 out of 10, Wonderful, (135)
"Excellent bed and breakfast, room was clean and comfortable."
The price is ￥43,488
￥48,272 total
includes taxes & fees
Aug 11 - Aug 12
Manor House Inn
Granville House
Enjoy a leisurely meal in this beautifully set dining area with a long table, adorned with pastries and bread.

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 ￥36,583
￥40,863 total
includes taxes & fees
Aug 17 - Aug 18
Granville House
The Inn at Stockbridge
Stroll through the serene park and enjoy the soothing sounds of the multi-tiered fountain surrounded by lush trees and a shaded walkway.

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
The Inn at Stockbridge
Devonfield Inn B&B
Stunning two-story house with a central entrance and beautifully manicured lawn.

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
Inn at Kenmore Hall
Guests can enjoy a peaceful atmosphere in this elegant space, featuring a console table with decorative items, a potted plant, and a framed photograph.

Inn at Kenmore Hall

3.0 star property
10.0 out of 10, Exceptional, (27)
"This is a beautiful property straight out of a magazine. Service was impeccable"
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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Top Sheffield Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Great price for area with clean and spacious suites. Would be perfect if offered on site breakfast."
Barbara 1-night trip
Posted 2 days ago
Berkshire Mountain Lodge

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. 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.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 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?
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.