20 Best B&B in Sheffield, MA - Bed and Breakfast from NT$3,444

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

NT$6,004 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

NT$3,961 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

NT$7,168 total

includes taxes & fees

Nov 8 - Nov 9

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

4. Granville House

Housatonic

Cynthia

NT$9,344 total

includes taxes & fees

Nov 18 - Nov 19

A two-story house with a brick entrance and a white facade.

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

Stockbridge

Philippe

NT$15,156 total

includes taxes & fees

Nov 29 - Nov 30

An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

6. Inn at Silver Maple Farm

East Chatham

Linda

NT$6,025 total

includes taxes & fees

Dec 2 - Dec 3

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

7. Changing Times Boutique Country Lodging

Craryville

Thomas

NT$7,348 total

includes taxes & fees

Nov 9 - Nov 10

8. The Inn at Stockbridge

Stockbridge

Kimberly

NT$10,279 total

includes taxes & fees

Nov 8 - Nov 9

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

9. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

NT$6,397 total

includes taxes & fees

Nov 9 - Nov 10

A two-story building with a sign reading "Chambéry Inn".

10. Chambery Inn

Lee

Alexandra

NT$7,716 total

includes taxes & fees

Dec 6 - Dec 7

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

11. Inn at Pine Plains

Pine Plains

teresina

NT$10,205 total

includes taxes & fees

Nov 9 - Nov 10

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

12. Shaker Mill Inn

West Stockbridge

Mahadeva

NT$5,218 total

includes taxes & fees

Nov 8 - Nov 9

A large, two-story house with a well-maintained lawn and a fence.

13. Devonfield Inn B&B

Lee

Sebastien

NT$13,521 total

includes taxes & fees

Nov 13 - Nov 14

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

14. Whistler's Inn Bed & Breakfast

Lenox

George

NT$4,617 total

includes taxes & fees

Nov 6 - Nov 7

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

15. Brook Farm Inn

Lenox

Carrie

NT$6,336 total

includes taxes & fees

Dec 1 - Dec 2

View all properties

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

Wilder House Berkshires

Sheffield

10/10 Excellent

Liliana

Blackberry River Inn

Norfolk

10/10 Excellent

Brandon

Devonfield Inn B&B

Lee

10/10 Excellent

Anonymous traveler

Locust Tree Bed and Breakfast LLC

East Canaan

10/10 Excellent

rose

Shaker Mill Inn

West Stockbridge

10/10 Excellent

This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...

Joe

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

Stockbridge

10/10 Excellent

Charles

Inn at Pine Plains

Pine Plains

10/10 Excellent

Kevin

Changing Times Boutique Country Lodging

Craryville

10/10 Excellent

Our second time staying here was even more lovely than the first! We brought more family members after our great experience last year. We love the easy check in, cozy comfortable rooms, lots of extras (books and DVDs in the hallway, sweet treats downstairs and in the rooms) and Loretta is the BEST host! She makes an exquisite breakfast and accommodates our early start time. Can’t wait to stay here again.

Kathleen

Inn at Silver Maple Farm

East Chatham

10/10 Excellent

Michelle

The Cornell Inn, Lenox & The Berkshires

Lenox

10/10 Excellent

Lawrence

The Inn at Stockbridge

Stockbridge

10/10 Excellent

Kevin

Brook Farm Inn

Lenox

10/10 Excellent

roberta

Chambery Inn

Lee

10/10 Excellent

Elaine

Whistler's Inn Bed & Breakfast

Lenox

10/10 Excellent

eli

A vintage black car parked on a road with a white fence and trees in the background.

Jenny's Country Manor

Red Hook

10/10 Excellent

Elyssamay

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.

Search B&B in Sheffield

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. Inn at Silver Maple Farm

7. Changing Times Boutique Country Lodging

8. The Inn at Stockbridge

9. The Cornell Inn, Lenox & The Berkshires

10. Chambery Inn

11. Inn at Pine Plains

12. Shaker Mill Inn

13. Devonfield Inn B&B

14. Whistler's Inn Bed & Breakfast

15. Brook Farm Inn

Learn more about Sheffield

Top reviews in Sheffield

Wilder House Berkshires

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?