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

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. 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 heart of downtown. Enjoy the free cooked breakfast and outdoor pool.

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

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

Mark

SAR 776 total

includes taxes & fees

14 Sep - 15 Sep

2. Locust Tree Bed and Breakfast LLC

East Canaan

Nicholas

SAR 453 total

includes taxes & fees

8 Sep - 9 Sep

3. Blackberry River Inn

Norfolk

Rachel

SAR 635 total

includes taxes & fees

10 Sep - 11 Sep

4. Manor House Inn

Norfolk

Kevin

SAR 1,275 total

includes taxes & fees

29 Sep - 30 Sep

Desk, laptop workspace, iron/ironing board (on request), WiFi (free)

5. Granville House

Housatonic

Nicole

SAR 940 total

includes taxes & fees

14 Sep - 15 Sep

Suite, Private Bathroom (RedBird Suite) | View from room

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

Stockbridge

Philippe

SAR 1,500 total

includes taxes & fees

28 Sep - 29 Sep

7. Devonfield Inn B&B

Lee

Richard

SAR 1,674 total

includes taxes & fees

8 Sep - 9 Sep

8. The Inn at Stockbridge

Stockbridge

Jodi

SAR 1,660 total

includes taxes & fees

14 Sep - 15 Sep

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

"Clean, comfortable,and a great location for attending events at Tanglewood."

The Yankee Inn

10/10 Excellent

"On an overpriced holiday weekend in the Berkshires, Yankee Inn was a great balance of price and amenities. The indoor pool was nicer than most, and the hot tub was great. Outdoor pool was a bit oddly placed between the parking lot and the main road, but nice as well. Both very clean. Room was spacious and clean, beds were comfortable, though I think they were doubles rather than queens. The included breakfast was on the very good end of standard - the fruit was fresh and delicious, there were both eggs and waffles, plus cereal, yogurt, bacon/sausage. Meh on the pastries, and the coffee was terribly watery. My true only gripe is that there was truly not a single place to hang wet bathing suits that didn't result in them dripping all over the floor. Had we been on the 2nd floor, we would have had an outside railing, but on the first floor there was none. With 4 people using the pool and hot tub, it was an annoyance. Overall, great place for a quick stay."

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. 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 heart of downtown. Enjoy the free cooked breakfast and outdoor pool.

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 Three Mile Pond Wildlife Management Area 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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates