Sheffield B&B: Find a 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. 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. Chambery Inn : 9 rooms. Located 14.7 mi (23.7 km) from the core of Sheffield. Enjoy the private garden and snack bar/deli.

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

includes taxes & fees

13 Sept - 14 Sept

2. Locust Tree Bed and Breakfast LLC

East Canaan

Kay

includes taxes & fees

15 Aug - 16 Aug

3. Blackberry River Inn

Norfolk

Leslie

includes taxes & fees

23 Aug - 24 Aug

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

4. Granville House

Housatonic

Nicole

includes taxes & fees

17 Aug - 18 Aug

5. Manor House Inn

Norfolk

Kevin

includes taxes & fees

31 Aug - 1 Sept

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

Stockbridge

Philippe

includes taxes & fees

31 Aug - 1 Sept

7. The Inn at Stockbridge

Stockbridge

Michele

includes taxes & fees

13 Sept - 14 Sept

8. Devonfield Inn B&B

Lee

Richard

includes taxes & fees

3 Sept - 4 Sept

Premium bedding, desk, laptop workspace, blackout curtains

9. Changing Times Boutique Country Lodging

Craryville

Jamie

includes taxes & fees

17 Aug - 18 Aug

10. Whistler's Inn Bed & Breakfast

Lenox

Mary

includes taxes & fees

1 Sept - 2 Sept

11. Inn at Pine Plains

Pine Plains

Katherine

includes taxes & fees

16 Aug - 17 Aug

12. Shaker Mill Inn

West Stockbridge

Mervin

includes taxes & fees

8 Sept - 9 Sept

13. Chambery Inn

Lee

Joseph

includes taxes & fees

13 Sept - 14 Sept

14. Inn at Silver Maple Farm

East Chatham

Erdem

includes taxes & fees

26 Aug - 27 Aug

15. The Cornell Inn, Lenox & The Berkshires

Lenox

Edward

includes taxes & fees

25 Aug - 26 Aug

Premium bedding, iron/ironing board, free WiFi, individually decorated

16. 33 Main

Lenox

Tatyana

includes taxes & fees

13 Sept - 14 Sept

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Top Sheffield Hotel Reviews

Little Cat Lodge

10/10 Excellent

"Absolutely love this place! Can’t wait to come back."

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

8/10 Good

"Shower base was very slippery-dangerous. Air-conditioning controls were poor. Thermostat was difficult to adjust and there was no ability to direct the cold air from the fan away from directly blowing on the bed. Had to move furniture to block it. Everything else was fine."

The Yankee Inn

10/10 Excellent

"Nice facility, good location, clean room, helpful staff. The pool was great as well. The breakfast could be enhanced with real eggs, some gluten free option. Also, I asked one of the servers who was replenishing food containers if there was an alternative to dairy milk for my oatmeal and she said no. Another guest heard my question and pointed me to the almond milk. It would be helpful if your staff could be aware of all of the offerings! Otherwise, we had a wonderful stay."

The Whitlock

10/10 Excellent

"We visited on a Tanglewood concert night in August. Check-in process was super easy and staff was reachable almost immediately via text. Very clean, updated and well-appointed room. Bar area was quiet but someone was always accessible to get us ice or an adult beverage. Complimentary water & coffee. Lovely outdoor courtyard where we enjoyed the fire pit post-concert. Great location… walkable to all shops and restaurants! Would highly recommend and will definitely stay here again!"

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Loved our two-day stay at the Black Swan Inn. We were in the area because we were taking a few programs at the Kripalu Center for one of the days. The room itself was clean, the hall areas could do with better maintenance (which is why I gave that 4 stars) The staff was helpful with any questions. Continental breakfast was decent (though they could do with better coffee). We wished we could have enjoyed the Indian restaurant "Mint" next door, which I hear is really good, but they were closed on Tuesdays, so it was a matter of timing..., but we hope to have a chance next time we are in the area. One of my favorite parts of the property is that it sits by a clean lovely lake, and there are seating areas to enjoy the view anytime of day just to unwind. They also have kayak rentals for those who enjoy the activity. Another wonderful treat- it is near High Lawn Farm, only a 3-min drive from the Inn. It is beautiful there, and cute Jersey cows roam freely, when they are ready they go on their own time into a building where they lay on heated water beds while being milked (I kid you not!). Their dairy products and ice-cream are excellent, worth taking the short drive there. The town center of Lee has some nice restaurants and boutiques within a 5-8 min drive. It was a memorable stay and hope to be back there again soon."

Find out more about Sheffield

Sheffield B&B information

Number of reviews	3,870
Accommodation	30 B&B
Lowest Price	S$155
Highest Price	S$910

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. Chambery Inn: 9 rooms. Located 14.7 mi (23.7 km) from the core of Sheffield. Enjoy the private garden and snack bar/deli.

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 Three Mile Pond Wildlife Management Area 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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