Top B&B in Sheffield in 2026

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

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Our top choices for Sheffield bed & breakfast

1. Wilder House Berkshires

Sheffield

Jennifer

5.730.578 ₫ total

includes taxes & fees

1 Sept - 2 Sept

2. Locust Tree Bed and Breakfast LLC

East Canaan

Regina

3.148.919 ₫ total

includes taxes & fees

6 Sept - 7 Sept

3. Blackberry River Inn

Norfolk

Rachel

5.698.043 ₫ total

includes taxes & fees

1 Sept - 2 Sept

4. Granville House

Housatonic

Nicole

8.010.640 ₫ total

includes taxes & fees

3 Sept - 4 Sept

5. Manor House Inn

Norfolk

Kevin

9.523.425 ₫ total

includes taxes & fees

1 Sept - 2 Sept

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

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

Stockbridge

Philippe

10.415.810 ₫ total

includes taxes & fees

28 Sept - 29 Sept

7. The Inn at Stockbridge

Stockbridge

Jodi

11.530.388 ₫ total

includes taxes & fees

13 Sept - 14 Sept

8. Devonfield Inn B&B

Lee

Richard

11.331.152 ₫ total

includes taxes & fees

3 Sept - 4 Sept

Deluxe Room, 1 King Bed, Ensuite (2nd Floor)

9. Changing Times Boutique Country Lodging

Craryville

Thomas

5.841.472 ₫ total

includes taxes & fees

2 Sept - 3 Sept

10. Inn at Silver Maple Farm

East Chatham

Erdem

4.059.823 ₫ total

includes taxes & fees

1 Sept - 2 Sept

11. Chambery Inn

Lee

Richard

7.864.603 ₫ total

includes taxes & fees

30 Sept - 1 Oct

12. Shaker Mill Inn

West Stockbridge

Mervin

4.748.855 ₫ total

includes taxes & fees

8 Sept - 9 Sept

13. Whistler's Inn Bed & Breakfast

Lenox

Mary Anna

4.640.319 ₫ total

includes taxes & fees

13 Sept - 14 Sept

14. Inn at Pine Plains

Pine Plains

Mary

8.112.702 ₫ total

includes taxes & fees

1 Sept - 2 Sept

15. The Cornell Inn, Lenox & The Berkshires

Lenox

Edward

6.076.095 ₫ total

includes taxes & fees

8 Sept - 9 Sept

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Top Sheffield Hotel Reviews

Berkshire Mountain Lodge

8/10 Good

"Best buy in the area during the high season. Spacious room and great location. Only negative is that property is a bit dated but recent renovations have been made."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"We had a fantastic stay at the Black Swan Inn in Lee, MA. Our room was incredibly clean, comfortable, and featured a beautiful view of the lake. Both check-in and check-out were completely hassle-free .A special shoutout goes to Carrie, the breakfast attendant! The breakfast area was exceptionally clean and well-stocked thanks to her hard work. Carrie was not only helpful, pleasant, and polite, but she also worked tirelessly to ensure all food items were fresh and fully available. Her excellent service truly made our mornings. We highly recommend this inn!"

Quality Inn Lee - Lenox South

8/10 Good

"Very nice and clean motel...better than I thought it would be, so we felt a lot better about staying there. We were a bit disappointed about the breakfast portion of the day so went out for brunch instead. The breakfast sandwiches weren't that great and not many tables to sit at. But overall, the rooms and bathrooms were very clean and modern."

Berkshires Untold

10/10 Excellent

"Although an excellent 2-night stay, our comments are intended to make future stays even better. Room temperature: virtually impossible to maintain a comfort level. Basically it was too cold in spite of raising the thermostat temp. At 80 when the heat came on, it was much too hot! Room lighting: too dark; only the bathroom was well lit. Bathroom moisture: in the absence of a ventilation or fan, the bathroom remained damp after a shower and keeping the door open resulted in everything in the bedroom becoming damp. But the positives far outweigh these few items."

The Red Lion Inn

10/10 Excellent

"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"

Find out more about Sheffield

Sheffield B&B information

Number of reviews	2,517
Accommodation	30 B&B
Lowest Price	3.148.919 ₫
Highest Price	11.530.388 ₫

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'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 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?

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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Room 1

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. Manor House Inn

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

7. The Inn at Stockbridge

8. Devonfield Inn B&B

9. Changing Times Boutique Country Lodging

10. Inn at Silver Maple Farm

11. Chambery Inn

12. Shaker Mill Inn

13. Whistler's Inn Bed & Breakfast

14. Inn at Pine Plains

15. The Cornell Inn, Lenox & The Berkshires

Top Sheffield Hotel Reviews

Berkshire Mountain Lodge

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Quality Inn Lee - Lenox South

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Little Cat Lodge

Berkshires Untold

Quality Inn Great Barrington

The Red Lion Inn

Find out more about Sheffield

Sheffield B&B information

Frequently asked questions

Explore a world of travel with Expedia

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. Manor House Inn

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

7. The Inn at Stockbridge

8. Devonfield Inn B&B

9. Changing Times Boutique Country Lodging

10. Inn at Silver Maple Farm

11. Chambery Inn

12. Shaker Mill Inn

13. Whistler's Inn Bed & Breakfast

14. Inn at Pine Plains

15. The Cornell Inn, Lenox & The Berkshires

Top Sheffield Hotel Reviews

Berkshire Mountain Lodge

Find out more about Sheffield

Sheffield B&B information

Frequently asked questions

Explore a world of travel with Expedia