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Check prices for these dates

Next weekend
5 Dec - 7 Dec
In two weeks
12 Dec - 14 Dec
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26 Dec - 28 Dec
In two months
23 Jan - 25 Jan

Featured B&B in Sheffield

Wilder House Berkshires Room 3
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 AU$266
includes taxes & fees
9 Dec - 10 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 AU$176
includes taxes & fees
2 Dec - 3 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 AU$260
includes taxes & fees
30 Nov - 1 Dec
Changing Times Boutique Country Lodging
Library
Blackberry River Inn

Blackberry River Inn

3.0 star property
Norfolk
9.4 out of 10, Exceptional, (159)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is AU$292
includes taxes & fees
26 Nov - 27 Nov
Blackberry River 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 AU$537
includes taxes & fees
30 Nov - 1 Dec
Manor House Inn
Porch
Lakehouse Inn

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (289)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is AU$334
includes taxes & fees
4 Dec - 5 Dec
Lakehouse 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
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 AU$499
includes taxes & fees
24 Dec - 25 Dec
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, (133)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Luxury Room, 1 King Bed, Bathtub
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 AU$737
includes taxes & fees
4 Dec - 5 Dec
33 Main
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 AU$479
includes taxes & fees
26 Nov - 27 Nov
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
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, (412)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is AU$187
includes taxes & fees
26 Nov - 27 Nov
Locust Tree Bed and Breakfast LLC
Individually decorated, individually furnished, desk, laptop workspace
Granville House

Granville House

3.0 star property
Housatonic
10.0 out of 10, Exceptional, (87)
"Outstanding all around!"
United States
Jonathan
The price is AU$344
includes taxes & fees
4 Dec - 5 Dec
Granville House
2 Bedrooms 1 Bath
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 AU$339
includes taxes & fees
1 Dec - 2 Dec
Tanglewood Suites
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, (1001)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is AU$283
includes taxes & fees
26 Nov - 27 Nov
The Cornell Inn, Lenox & The Berkshires
Business centre
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 AU$715
includes taxes & fees
8 Dec - 9 Dec
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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 AU$478
includes taxes & fees
26 Nov - 27 Nov
Experience Timeless Elegance in The Edith Wharton Room!
1 bedroom, WiFi, bed sheets
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 AU$510
includes taxes & fees
26 Nov - 27 Nov
Elegant Carriage House room with a queen bed and private patio.
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 AU$544
includes taxes & fees
26 Nov - 27 Nov
Cozy Carriage House room with a double bed and private balcony
Terrace/patio
Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay

Lenox
The price is AU$575
includes taxes & fees
26 Nov - 27 Nov
Historic Susan B. Anthony Room - Cozy & Charming Stay
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

Monument Mountain Motel

Monument Mountain Motel

10/10 Excellent
"Great place to stay! "
HEATHER 1-night trip
Posted 3 days ago
Monument Mountain Motel

Find out more about Sheffield

Sheffield B&B information

Number of reviews
3,003
Accommodation
41 B&B
Lowest Price
AU$176
Highest Price
AU$737

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. Blackberry River Inn: 14 rooms. 9.2 mi (14.9 km) from the city centre. 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 decor. Chambery Inn: 9 rooms. 14.7 mi (23.7 km) from the city centre. Enjoy the private garden and snack bar/deli. Shaker Mill Inn: 9 rooms. Located 15.6 mi (25.1 km) from the core of Sheffield.
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 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?
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.

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