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Check prices for these dates

Next weekend
6 Feb - 8 Feb
In two weeks
13 Feb - 15 Feb
In one month
27 Feb - 1 Mar
In two months
27 Mar - 29 Mar

Our top choices for Sheffield bed & breakfast

Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (43 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
Wilder House Berkshires
Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (414 reviews)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is €101
includes taxes & fees
31 Jan - 1 Feb
Locust Tree Bed and Breakfast LLC
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (291 reviews)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is €141
includes taxes & fees
31 Jan - 1 Feb
Lakehouse Inn
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (167 reviews)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is €158
includes taxes & fees
4 Feb - 5 Feb
Blackberry River Inn
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (374 reviews)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
The price is €234
includes taxes & fees
1 Feb - 2 Feb
The Inn at Stockbridge
Front of property – evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (134 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Individually decorated, individually furnished, desk, laptop workspace

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (93 reviews)
"Absolutely magical at Christmas time! It was only for a quick overnight but felt like time stood still while we were there. The service was impeccable and Terry and Terri were a delight! I look forward to returning. "
United States
Jennifer
The price is €186
includes taxes & fees
1 Feb - 2 Feb
Granville House
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,000 reviews)
"The Inn was very nice and the staff was super friendly and attentive."
United States
Steven
The price is €129
includes taxes & fees
2 Feb - 3 Feb
The Cornell Inn, Lenox & The Berkshires
Luxury Room, 1 King Bed, Bathtub

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is €383
includes taxes & fees
23 Feb - 24 Feb
33 Main
Suite, Private Bathroom (RedBird Suite) | View from room

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

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is €313
includes taxes & fees
23 Feb - 24 Feb
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (444 reviews)
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
The price is €100
includes taxes & fees
1 Feb - 2 Feb
Shaker Mill Inn
Aerial view

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (100 reviews)
"Great property, very comfortable, incredible staff, easy access to skiing in the area!"
United States
Dominick
The price is €121
includes taxes & fees
1 Feb - 2 Feb
Inn at Silver Maple Farm
3 bedrooms, bed sheets

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is €244
includes taxes & fees
1 Feb - 2 Feb
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Free daily continental breakfast

Inn at Pine Plains

Inn at Pine Plains
3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (303 reviews)
"Great stay"
United Kingdom
Katherine
The price is €234
includes taxes & fees
2 Feb - 3 Feb
Inn at Pine Plains
Deluxe Room, 1 King Bed, Ensuite (2nd Floor)

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (109 reviews)
"Great experience, looking forward to staying again."
United States
Greg
The price is €131
includes taxes & fees
5 Feb - 6 Feb
Changing Times Boutique Country Lodging
1 bedroom, WiFi, bed sheets, wheelchair access

Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is €244
includes taxes & fees
4 Feb - 5 Feb
Experience Timeless Elegance in The Edith Wharton Room!
Lobby

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
Richmond
10.0 out of 10, Exceptional, (27 reviews)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is €527
includes taxes & fees
31 Jan - 1 Feb
Inn at Kenmore Hall
Front of property

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164 reviews)
"Everything was perfect - location and accommodation."
United States
Christopher
Brook Farm Inn
Interior

Elegant Carriage House room with a queen bed and private patio.

Elegant Carriage House room with a queen bed and private patio.
Lenox
The price is €308
includes taxes & fees
1 Mar - 2 Mar
Elegant Carriage House room with a queen bed and private patio.
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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Great stay. The only thing I would say - and I’ve been staying at the hotel since the 80s - it might be time for a few updates here and there. It runs the risk of going from rustic charm to grandma’s house in the not tooooo distant future. "
Simon 1-night trip
Posted 2 days ago
The Red Lion Inn

Find out more about Sheffield

Sheffield B&B information

Number of reviews
3,432
Accommodation
41 B&B
Lowest Price
€100
Highest Price
€527

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, Thom Reed UFO Monument Park and Bartholomews Cobble 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: Wilder House Berkshires: 5 rooms. 0.3 mi (0.5 km) from the heart of Sheffield. Enjoy the free cooked breakfast and unique decor. The Cornell Inn, Lenox & The Berkshires: 18.1 mi (29.1 km) from the city centre. Enjoy the free full breakfast and unique decor. 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. Shaker Mill Inn: 9 rooms. 15.6 mi (25.1 km) from the city centre. Brook Farm Inn: 15 rooms. Located 17.1 mi (27.5 km) from the core of Sheffield. Enjoy the free cooked breakfast and outdoor pool.
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, Housatonic River and Thom Reed UFO Monument Park are some notable spots. You should 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?
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.