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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Sheffield bed & breakfast

Interior detail

1. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (72 reviews)
"Clean, cozy, and charming. The breakfast is delicious and all went smoothly."
United States
Liliana
The price is P10,315
P11,521 total
includes taxes & fees
Nov 15 - Nov 16
Wilder House Berkshires
A sign for 'The Logust Tree Bed & Breakfast' with a contact number.

2. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (455 reviews)
"Wonderful stay, and wonderful breakfast."
United States
Daniel
The price is P6,609
P7,601 total
includes taxes & fees
Nov 18 - Nov 19
Locust Tree Bed and Breakfast LLC
A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

3. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (256 reviews)
"Great Breakfast Bed was okay Room very quaint hotel was very nice inside"
United States
Melanie
The price is P11,960
P13,754 total
includes taxes & fees
Nov 15 - Nov 16
Blackberry River Inn
A dining table with pastries, a coffee pot, and a vase of sunflowers.

4. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (110 reviews)
"We loved everything about Granville House, especially the innkeepers! Wonderful atmosphere and excellent food! It was definitely the highlight of our trip to New England."
United States
Cynthia
The price is P15,989
P17,859 total
includes taxes & fees
Nov 20 - Nov 21
Granville House
Front of property

5. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (110 reviews)
"Wonderful place… clean, cosy room, comfy bed, friendly staff, great breakfast. Delightful location near Norman Rockwell museum."
United States
Kimberly
The price is P14,514
P17,023 total
includes taxes & fees
Nov 15 - Nov 16
The Inn at Stockbridge
A two-story house with a brick entrance and a white facade.

6. 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
9.4 out of 10, Exceptional, (120 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is P24,041
P29,083 total
includes taxes & fees
Nov 28 - Nov 29
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

7. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (118 reviews)
"Perfect location for hiking, hanging out and Tanglewood Comfortable and charming common space and cozy nicely decorated rooms Generous breakfast and snacks throughout the day We’ll be back"
United States
Linda
The price is P10,323
P11,562 total
includes taxes & fees
Dec 3 - Dec 4
Inn at Silver Maple Farm
A snow-covered outdoor area with a patio, seating, and a covered dining area.

8. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.4 out of 10, Exceptional, (1,000 reviews)
"Lovely room, comfortable bed and a nice breakfast."
United Kingdom
judith
The price is P10,702
P12,275 total
includes taxes & fees
Nov 15 - Nov 16
The Cornell Inn, Lenox & The Berkshires
A two-story building with a sign reading "Chambéry Inn".

9. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (390 reviews)
"An absolutely perfect getaway spot! Beautiful rooms, great service, and an ideal location. Highly recommend and we will be going back."
United States
Alexandra
The price is P13,321
P14,879 total
includes taxes & fees
Dec 13 - Dec 14
Chambery Inn
A breakfast table with a teapot, milk, and a bagel, set against a brick wall with a framed picture above.

10. Inn at Pine Plains

Inn at Pine Plains
3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (318 reviews)
"good location/ walkable to down town !"
United States
teresina
The price is P17,310
P19,582 total
includes taxes & fees
Nov 15 - Nov 16
Inn at Pine Plains
A bedroom with a large mural of a waterfall, two bedside lamps, a bed with multiple pillows, and a nightstand with a lamp.

11. Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (128 reviews)
"A great place to stay!"
United States
Thomas
The price is P12,589
P14,100 total
includes taxes & fees
Dec 8 - Dec 9
Changing Times Boutique Country Lodging
A red building with a sign reading "Shaker Mill Inn."

12. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (483 reviews)
"Loved the location, fireplace and vibe"
United States
Mahadeva
The price is P9,127
P10,013 total
includes taxes & fees
Nov 16 - Nov 17
Shaker Mill Inn
A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

13. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (141 reviews)
"Wonderful location and hosts are amazing. Breakfast was great. Clean."
United States
Sebastien
The price is P23,227
P25,945 total
includes taxes & fees
Nov 13 - Nov 14
Devonfield Inn B&B
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

14. Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.6 out of 10, Exceptional, (178 reviews)
"Breakfast was not only delicious, the room was sweet and bright and staff very attentive."
United States
Carrie
The price is P10,390
P12,109 total
includes taxes & fees
Nov 13 - Nov 14
Brook Farm Inn
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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Learn more about Sheffield

Tucked in the Berkshires, this charming town offers scenic hikes at Bartholomew's Cobble and local art at the Sheffield Historical Society. Catch live performances at the Berkshire Theatre Festival in nearby Stockbridge or sample farm-fresh produce at the weekend farmers' market on the town green.

See all hotels in Sheffield
A lakeside town with autumn foliage, a bridge, and a rocky shoreline.

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. 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.

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 Suter Farm 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.