Sheffield B&B: Best Bed and Breakfast 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. Locust Tree Bed and Breakfast LLC : 7 rooms. Situated 6.8 mi (11 km) from the heart of Sheffield. Blackberry River Inn : 14 rooms. 9.2 mi (14.9 km) from the city centre. Enjoy the free cooked breakfast and outdoor pool. Shaker Mill Inn : 9 rooms. Located 15.6 mi (25.1 km) from the core of Sheffield.

A covered wooden structure with a sloped roof, surrounded by greenery and trees.

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Our top choices for Sheffield bed & breakfast

Wilder House Berkshires

Sheffield

Jennifer

includes taxes & fees

7 Jul - 8 Jul

Locust Tree Bed and Breakfast LLC

East Canaan

Larry

includes taxes & fees

12 Jul - 13 Jul

Blackberry River Inn

Norfolk

Maura

includes taxes & fees

8 Jul - 9 Jul

The Cornell Inn, Lenox & The Berkshires

Lenox

Arthur

includes taxes & fees

7 Jul - 8 Jul

Individually decorated, individually furnished, desk, laptop workspace

Granville House

Housatonic

Nicole

includes taxes & fees

7 Jul - 8 Jul

The Berkshire Mountain Inn

Great Barrington

Robert

includes taxes & fees

15 Jul - 16 Jul

Whistler's Inn Bed & Breakfast

Lenox

Stacey

includes taxes & fees

7 Jul - 8 Jul

Chambery Inn

Lee

robert

includes taxes & fees

7 Jul - 8 Jul

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Top Sheffield Hotel Reviews

Berkshire Mountain Lodge

10/10 Excellent

"This was a great place to stay. It was clean and quiet. The staff were really helpful And friendly. Although the decor is a bit dated the room was clean and comfortable. There a big kitchen (for a hotel), dining table, sitting room, separate bedroom And a big bathroom. The property also had a large sitting room off the lobby with couches, tables and chairs and a tv. They had movies showing there at night and movies you could borrow for your room. There were walking trails and andarandak chairs all over the property to sit and relax outside. This is a wonderful place to stay and I would stay here again if I was in the area."

The Whitlock

8/10 Good

"I was initially worried seeing mixed reviews about The Whitlock but we had a wonderful time. Location cannot be beat - walk out the door into town and everything Lenox has to offer. Room was clean, cozy and comfortable. AC was strong even during a heatwave. SmartTV with all of the streaming channels. The lobby and patio space were great, and there is a little convenience area to buy waters or juice. The staff were responsive and helpful when we wanted to switch rooms. Wonderful trip all around, I recommend the Whitlock for your trip to Lenox!"

Find out more about Sheffield

Sheffield B&B information

Number of reviews	4,297
Accommodation	41 B&B
Lowest Price	€106
Highest Price	€719

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. Locust Tree Bed and Breakfast LLC: 7 rooms. Situated 6.8 mi (11 km) from the heart of Sheffield. Blackberry River Inn: 14 rooms. 9.2 mi (14.9 km) from the city centre. Enjoy the free cooked breakfast and outdoor pool. Shaker Mill Inn: 9 rooms. Located 15.6 mi (25.1 km) from the core of Sheffield.

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 Magnolia Bluffs Casino and Bartholomew's Cobble 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.

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