20 Best B&B in Sheffield, MA - Bed and Breakfast from AED 385

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

A room with a wooden floor, two red armchairs, a small table, and a window with a view of trees.

1. Wilder House Berkshires

Sheffield

Liliana

AED 712 total

includes taxes & fees

16 Nov - 17 Nov

A bedroom with a wooden bed frame, floral bedding, a nightstand with a lamp, and a dresser with drawers.

2. Locust Tree Bed and Breakfast LLC

East Canaan

Daniel

AED 444 total

includes taxes & fees

15 Nov - 16 Nov

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

3. Granville House

Housatonic

Cynthia

AED 940 total

includes taxes & fees

20 Nov - 21 Nov

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

4. Blackberry River Inn

Norfolk

Melanie

AED 778 total

includes taxes & fees

22 Nov - 23 Nov

5. The Inn at Stockbridge

Stockbridge

Kimberly

AED 941 total

includes taxes & fees

15 Nov - 16 Nov

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

Stockbridge

Philippe

AED 1,697 total

includes taxes & fees

28 Nov - 29 Nov

A spacious kitchen with wooden beams, a dining area with a large table and chairs, and a view of the outdoors through large windows.

7. Inn at Silver Maple Farm

East Chatham

Linda

AED 634 total

includes taxes & fees

6 Dec - 7 Dec

A vintage turquoise Ford truck parked in front of a building labeled "CHAMBÉRY INN."

8. Chambery Inn

Lee

Alexandra

AED 778 total

includes taxes & fees

15 Nov - 16 Nov

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

9. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

AED 716 total

includes taxes & fees

15 Nov - 16 Nov

A dining area with a table set for breakfast, a chalkboard menu, and various kitchen utensils hanging on the wall.

10. Inn at Pine Plains

Pine Plains

teresina

AED 948 total

includes taxes & fees

24 Nov - 25 Nov

A fire pit with two Adirondack chairs, a table with drinks, and a house in the background.

11. Changing Times Boutique Country Lodging

Craryville

Thomas

AED 823 total

includes taxes & fees

16 Nov - 17 Nov

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

12. Shaker Mill Inn

West Stockbridge

Mahadeva

AED 584 total

includes taxes & fees

15 Nov - 16 Nov

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

Lee

Sebastien

AED 1,514 total

includes taxes & fees

16 Nov - 17 Nov

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

14. Experience Timeless Elegance in The Edith Wharton Room!

Lenox

AED 1,242 total

includes taxes & fees

15 Nov - 16 Nov

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

AED 1,313 total

includes taxes & fees

16 Nov - 17 Nov

A neatly made bed with a textured white cover, a headboard, and two pillows, one of which is patterned. There is a small bedside table with a lamp and a painting of a landscape on the wall.

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

Lenox

AED 1,242 total

includes taxes & fees

15 Nov - 16 Nov

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

AED 1,385 total

includes taxes & fees

16 Nov - 17 Nov

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

AED 1,460 total

includes taxes & fees

16 Nov - 17 Nov

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

AED 707 total

includes taxes & fees

15 Nov - 16 Nov

A bedroom with a bed, a fireplace, a ceiling fan, and a door.

20. Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Lenox

AED 1,788 total

includes taxes & fees

17 Nov - 18 Nov

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

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 Inn at Stockbridge

Stockbridge

10/10 Excellent

Kevin

Inn at Silver Maple Farm

East Chatham

10/10 Excellent

Michelle

The Cornell Inn, Lenox & The Berkshires

Lenox

10/10 Excellent

Lawrence

Devonfield Inn B&B

Lee

10/10 Excellent

Anonymous traveler

Inn at Pine Plains

Pine Plains

10/10 Excellent

Kevin

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

Stockbridge

10/10 Excellent

Charles

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

Chambery Inn

Lee

10/10 Excellent

Elaine

Brook Farm Inn

Lenox

10/10 Excellent

roberta

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. Granville House

4. Blackberry River Inn

5. The Inn at Stockbridge

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

7. Inn at Silver Maple Farm

8. Chambery Inn

9. The Cornell Inn, Lenox & The Berkshires

10. Inn at Pine Plains

11. Changing Times Boutique Country Lodging

12. Shaker Mill Inn

13. Devonfield Inn B&B

14. Experience Timeless Elegance in The Edith Wharton Room!

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

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

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. Experience Timeless Elegance in The Niles Johnson Room at The Cornell 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?