Sheffield B&B: Find the Best Bed and Breakfast from CA $146

Q: 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.

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Our top choices for Sheffield bed & breakfast

1. Wilder House Berkshires

Sheffield

Liliana

CA $256 total

includes taxes & fees

Nov 10 - Nov 11

A sign for 'The Logust Tree Bed & Breakfast' with a contact number.

2. Locust Tree Bed and Breakfast LLC

East Canaan

Daniel

CA $169 total

includes taxes & fees

Nov 6 - Nov 7

A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

3. Blackberry River Inn

Norfolk

Melanie

CA $284 total

includes taxes & fees

Nov 11 - Nov 12

A dining table with pastries, a coffee pot, and a vase of sunflowers.

4. Granville House

Housatonic

Cynthia

CA $398 total

includes taxes & fees

Nov 19 - Nov 20

A breakfast setup with plates of food, glasses of orange juice, and a pitcher of milk.

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

Stockbridge

Philippe

CA $615 total

includes taxes & fees

Dec 6 - Dec 7

6. The Inn at Stockbridge

Stockbridge

Kimberly

CA $438 total

includes taxes & fees

Nov 9 - Nov 10

A bedroom with a large bed, a desk, a chair, a television, and a window with curtains.

7. Chambery Inn

Lee

Alexandra

CA $273 total

includes taxes & fees

Nov 8 - Nov 9

A bedroom with a large mural of a waterfall, two bedside lamps, a bed with multiple pillows, and a nightstand with a lamp.

8. Changing Times Boutique Country Lodging

Craryville

Thomas

CA $313 total

includes taxes & fees

Nov 6 - Nov 7

A snow-covered outdoor area with a patio, seating, and a covered dining area.

9. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

CA $272 total

includes taxes & fees

Nov 9 - Nov 10

A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

10. Devonfield Inn B&B

Lee

Sebastien

CA $576 total

includes taxes & fees

Nov 13 - Nov 14

A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

11. Inn at Silver Maple Farm

East Chatham

Linda

CA $257 total

includes taxes & fees

Dec 2 - Dec 3

A red building with a sign reading "Shaker Mill Inn."

12. Shaker Mill Inn

West Stockbridge

Mahadeva

CA $222 total

includes taxes & fees

Nov 8 - Nov 9

A garden with a white gazebo, a brick pathway, and various plants and flowers.

13. Whistler's Inn Bed & Breakfast

Lenox

George

CA $215 total

includes taxes & fees

Nov 6 - Nov 7

A breakfast table with a teapot, milk, and a bagel, set against a brick wall with a framed picture above.

14. Inn at Pine Plains

Pine Plains

teresina

CA $435 total

includes taxes & fees

Nov 8 - Nov 9

A room with a dark green sofa, a small table with a vase of flowers, a desk with a lamp, and a window with curtains.

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

Lenox

CA $500 total

includes taxes & fees

Nov 9 - Nov 10

A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

16. Experience Timeless Elegance in The Edith Wharton Room!

Lenox

CA $472 total

includes taxes & fees

Nov 9 - Nov 10

A porch with a white railing, a potted plant, and a view of a garden.

17. Cozy Carriage House room with a double bed and private balcony

Lenox

CA $527 total

includes taxes & fees

Nov 15 - Nov 16

A wooden deck with Adirondack chairs and a small table, leading to a garden area with a swing set.

18. Historic Susan B. Anthony Room - Cozy & Charming Stay

Lenox

CA $556 total

includes taxes & fees

Nov 9 - Nov 10

A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

19. Brook Farm Inn

Lenox

Carrie

CA $270 total

includes taxes & fees

Dec 1 - Dec 2

A well-appointed bedroom with a large bed, a bedside table, a chair, and a bathroom visible through an open door.

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

Lenox

CA $472 total

includes taxes & fees

Nov 9 - Nov 10

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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.

Top reviews in Sheffield

Locust Tree Bed and Breakfast LLC

East Canaan

10/10 Excellent

Michel

Inn at Silver Maple Farm

East Chatham

10/10 Excellent

Timothy

Devonfield Inn B&B

Lee

10/10 Excellent

We stayed at the Devonfield Inn in mid-October during peak foliage season. The hotel is a wonderful historic home built in 1800 with much of its historic character preserved. Our hosts were so welcoming and made us feel at home. The room was very comfortable and breakfast was fantastic. In the morning, we got a special surprise to see a bear on the patio drinking from the fountain and robbing the bird feeder. Overall we highly recommend the Devonfield. We will definitely go back.

Lise

Chambery Inn

Lee

10/10 Excellent

Val

The Cornell Inn, Lenox & The Berkshires

Lenox

10/10 Excellent

Michael

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

Stockbridge

10/10 Excellent

Anonymous traveller

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.

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The Berkshires Vacation Rentals
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Find a Bed and Breakfast in Sheffield from CA $146

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Sheffield bed & breakfast

1. Wilder House Berkshires

2. Locust Tree Bed and Breakfast LLC

3. Blackberry River Inn

4. Granville House

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

6. The Inn at Stockbridge

7. Chambery Inn

8. Changing Times Boutique Country Lodging

9. The Cornell Inn, Lenox & The Berkshires

10. Devonfield Inn B&B

11. Inn at Silver Maple Farm

12. Shaker Mill Inn

13. Whistler's Inn Bed & Breakfast

14. Inn at Pine Plains

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

16. Experience Timeless Elegance in The Edith Wharton Room!

17. Cozy Carriage House room with a double bed and private balcony

18. Historic Susan B. Anthony Room - Cozy & Charming Stay

19. Brook Farm Inn

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

Learn more about Sheffield

Top reviews in Sheffield

Locust Tree Bed and Breakfast LLC

10/10 Excellent

Frequently Asked Questions

Searching for B&Bs in Sheffield?

How do you know if a B&B is a good option for you?

What are the top B&Bs in Sheffield?

When should I book my B&B in Sheffield?

What is there to do in Sheffield?

How can I get to and around Sheffield?

Explore a world of travel with Expedia