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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Sheffield bed & breakfast

Wilder House Berkshires Room 3 | Premium bedding, individually decorated, individually furnished
Wilder House Berkshires

Wilder House Berkshires

2.0 star property
Sheffield
9.8 out of 10, Exceptional, (38)
"Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you! "
United States
Allison
The price is AED 559
AED 625 total
includes taxes & fees
17 Dec - 18 Dec
Wilder House Berkshires
Garden
Shaker Mill Inn

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (436)
"Nice place, easy check in"
United States
Robert
The price is AED 396
AED 435 total
includes taxes & fees
10 Dec - 11 Dec
Shaker Mill Inn
Porch
Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging

3.5 star property
Craryville
10.0 out of 10, Exceptional, (109)
"Great experience, looking forward to staying again."
United States
Greg
The price is AED 551
AED 617 total
includes taxes & fees
10 Dec - 11 Dec
Changing Times Boutique Country Lodging
Library
Blackberry River Inn

Blackberry River Inn

3.0 star property
Norfolk
9.4 out of 10, Exceptional, (163)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is AED 604
AED 694 total
includes taxes & fees
10 Dec - 11 Dec
Blackberry River Inn
Front of property
Chambery Inn

Chambery Inn

3.0 star property
Lee
9.6 out of 10, Exceptional, (373)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Porch
Lakehouse Inn

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (290)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is AED 684
AED 802 total
includes taxes & fees
12 Dec - 13 Dec
Lakehouse Inn
Interior detail
Manor House Inn

Manor House Inn

3.0 star property
Norfolk
9.4 out of 10, Exceptional, (138)
"Excellent bed and breakfast, room was clean and comfortable."
United States
Kevin
The price is AED 1,160
AED 1,288 total
includes taxes & fees
14 Dec - 15 Dec
Manor House Inn
Exterior
The Inn at Stockbridge

The Inn at Stockbridge

4.0 star property
Lee
9.8 out of 10, Exceptional, (99)
"Well-run and elegant property. "
United States
Steven
The price is AED 921
AED 1,080 total
includes taxes & fees
1 Jan - 2 January 2026
The Inn at Stockbridge
Individually decorated, individually furnished, desk, laptop workspace
Granville House

Granville House

3.0 star property
Housatonic
10.0 out of 10, Exceptional, (89)
"Outstanding all around!"
United States
Jonathan
The price is AED 735
AED 821 total
includes taxes & fees
1 Jan - 2 January 2026
Granville House
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main

33 Main

4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is AED 1,585
AED 1,770 total
includes taxes & fees
5 Jan - 6 January 2026
33 Main
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)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Terrace/patio
Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

3.0 star property
East Canaan
9.0 out of 10, Wonderful, (413)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is AED 386
AED 443 total
includes taxes & fees
10 Dec - 11 Dec
Locust Tree Bed and Breakfast LLC
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 AED 995
AED 1,301 total
includes taxes & fees
10 Dec - 11 Dec
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Aerial view
Inn at Silver Maple Farm

Inn at Silver Maple Farm

3.0 star property
East Chatham
9.8 out of 10, Exceptional, (98)
"Great stay, comfortable place"
United States
barry
The price is AED 474
AED 531 total
includes taxes & fees
10 Dec - 11 Dec
Inn at Silver Maple Farm
2 Bedrooms 1 Bath | Premium bedding, iron/ironing board, free WiFi, bed sheets
Tanglewood Suites

Tanglewood Suites

2.5 star property
Stockbridge
6.4 out of 10, (22)
"NOT A REAL LOCATION. There was nothing there. Neighbors said this was a scam. Expedia ended up helping us find a local hotel room though the location was not as good. DO NOT BOOK THIS LOCATION -- it needs to be taken off the website."
United States
Elizabeth
The price is AED 804
AED 804 total
includes taxes & fees
10 Dec - 11 Dec
Tanglewood Suites
Business center
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)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is AED 1,403
AED 1,697 total
includes taxes & fees
5 Jan - 6 January 2026
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property
Lenox
9.0 out of 10, Wonderful, (1000)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is AED 614
AED 706 total
includes taxes & fees
10 Dec - 11 Dec
The Cornell Inn, Lenox & The Berkshires
1 bedroom, bed sheets
Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony

Lenox
The price is AED 1,116
AED 1,461 total
includes taxes & fees
10 Dec - 11 Dec
Cozy Carriage House room with a double bed and private balcony
Lobby
Inn at Kenmore Hall

Inn at Kenmore Hall

3.0 star property
Richmond
10.0 out of 10, Exceptional, (27)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is AED 1,561
AED 1,712 total
includes taxes & fees
16 Dec - 17 Dec
Inn at Kenmore Hall
Free daily continental breakfast
Inn at Pine Plains

Inn at Pine Plains

3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (301)
"Great stay"
United Kingdom
Katherine
The price is AED 909
AED 1,028 total
includes taxes & fees
10 Dec - 11 Dec
Inn at Pine Plains
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

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Great hospitality "
regina maria 1-night trip
Posted 1 day ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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, Thom Reed UFO Monument Park and Bartholomews Cobble 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. Blackberry River Inn: 14 rooms. 9.2 mi (14.9 km) from the downtown core. Enjoy the free cooked breakfast and outdoor pool. The Cornell Inn, Lenox & The Berkshires: Situated 18.1 mi (29.1 km) from the heart of Sheffield. Enjoy the free full breakfast and unique décor. Chambery Inn: 9 rooms. 14.7 mi (23.7 km) from the heart of downtown. Enjoy the private yard and deli. 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 Thom Reed UFO Monument Park 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.