Top B&B in Sheffield in 2026

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 decor. The Cornell Inn, Lenox & The Berkshires : 18.1 mi (29.1 km) from the city centre. Enjoy the free full breakfast and unique decor. 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 city centre.

A lakeside town with autumn foliage, a bridge, and a rocky shoreline.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Our top choices for Sheffield bed & breakfast

1. Wilder House Berkshires

Sheffield

Liliana

Rp3.325.379 total

includes taxes & fees

10 Nov - 11 Nov

A covered porch with white railings and rocking chairs.

2. Locust Tree Bed and Breakfast LLC

East Canaan

Daniel

Rp2.183.402 total

includes taxes & fees

15 Nov - 16 Nov

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

3. Blackberry River Inn

Norfolk

Melanie

Rp3.950.917 total

includes taxes & fees

11 Nov - 12 Nov

A dining area with a round table and four chairs, a radiator, and a window with a view of greenery.

4. Granville House

Housatonic

Cynthia

Rp5.174.973 total

includes taxes & fees

18 Nov - 19 Nov

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

Rp8.393.952 total

includes taxes & fees

26 Nov - 27 Nov

6. The Inn at Stockbridge

Stockbridge

Kimberly

Rp5.693.124 total

includes taxes & fees

8 Nov - 9 Nov

A crowded outdoor event with tents and people gathered in a grassy area.

7. Chambery Inn

Lee

Alexandra

Rp4.273.659 total

includes taxes & fees

6 Dec - 7 Dec

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

Rp4.069.632 total

includes taxes & fees

7 Nov - 8 Nov

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

9. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

Rp3.542.912 total

includes taxes & fees

9 Nov - 10 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.

10. Devonfield Inn B&B

Lee

Sebastien

Rp7.488.305 total

includes taxes & fees

13 Nov - 14 Nov

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

11. Inn at Silver Maple Farm

East Chatham

Linda

Rp3.337.098 total

includes taxes & fees

2 Dec - 3 Dec

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

12. Shaker Mill Inn

West Stockbridge

Mahadeva

Rp2.889.893 total

includes taxes & fees

8 Nov - 9 Nov

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

13. Whistler's Inn Bed & Breakfast

Lenox

George

Rp2.794.420 total

includes taxes & fees

8 Nov - 9 Nov

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

Rp5.625.198 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.

15. Brook Farm Inn

Lenox

Carrie

Rp3.489.645 total

includes taxes & fees

7 Dec - 8 Dec

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Top Sheffield Hotel Reviews

Berkshire Mountain Lodge

10/10 Excellent

"Very centrally located. Right next to a good little market. Very reasonable price for an apartment like room."

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"This place was amazing to stay at! The staff was friendly and helpful. The building was beautifully decorated inside and out, and it is in a safe location. Breakfast was very good. Only downside is that coffee was not available throughout the day (only served at breakfast). Overall, would definitely stay here again!"

the Alander

10/10 Excellent

"Room was fresh and super clean. Comfortable bed and the sheets and towels were soft and high quality. Staff was also super helpful getting us settled in. Cozy bar and dining room. However my rigatoni pasta bowl was puzzling. Raw uncooked plum canned tomatoes, raw zucchini cubes, and a handful of only slightly blanched broccoli raab sitting on top of it all! The freshly baked bread and home made butter service was wonderful though."

Find out more about Sheffield

Sheffield B&B information

Number of reviews	3,324
Accommodation	30 B&B
Lowest Price	Rp2.183.402
Highest Price	Rp8.393.952

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. The Cornell Inn, Lenox & The Berkshires: 18.1 mi (29.1 km) from the city centre. Enjoy the free full breakfast and unique decor. 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 city centre.

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 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?

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.

Explore a world of travel with Expedia

More ways to book

Book B&B in Sheffield on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates