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

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Check prices for these dates

Next weekend
Aug 21 - Aug 23
In two weeks
Aug 28 - Aug 30
In one month
Sep 11 - Sep 13
In two months
Oct 9 - Oct 11

Our top choices for Sheffield bed & breakfast

Interior detail

1. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (61 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is P12,633
P14,111 total
includes taxes & fees
Sep 13 - Sep 14
Wilder House Berkshires
Exterior

2. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (438 reviews)
"This is a quiet location and easy to find. It has a working-farm vibe rather than a luxury-vacation vibe. French toast was delicious. Guest meals are prepared in a home kitchen without a dishwasher or secondary sink."
United States
Kay
The price is P6,427
P7,391 total
includes taxes & fees
Aug 15 - Aug 16
Locust Tree Bed and Breakfast LLC
Library

3. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (203 reviews)
"Excellent breakfast, very nice staff."
United States
Leslie
The price is P11,630
P13,374 total
includes taxes & fees
Aug 16 - Aug 17
Blackberry River Inn
Desk, laptop workspace, iron/ironing board (on request), WiFi (free)

4. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (105 reviews)
"Beautiful home with warm and friendly hosts. The rooms were tastefully designed, the bed was very comfortable and the large bathroom was luxurious. The breakfast was absolutely delicious. We will definitely stay again next time we are in Great Barrington. "
United States
Nicole
The price is P16,832
P18,802 total
includes taxes & fees
Aug 17 - Aug 18
Granville House
Front of property

5. Manor House Inn

Manor House Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (139 reviews)
"Excellent bed and breakfast, room was clean and comfortable."
United States
Kevin
The price is P20,138
P22,353 total
includes taxes & fees
Aug 31 - Sep 1
Manor House Inn
View from room

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

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (114 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is P20,209
P24,447 total
includes taxes & fees
Aug 31 - Sep 1
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property

7. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (101 reviews)
"Our room was very clean and comfortable - exactly what we needed to rest well. Breakfast was excellent and we felt well taken care of. We are grateful for the friendly and welcoming hosts and their staff who listened to every need and graciously provided for us. We’ll definitely return for another stay when we’re in the area."
United Kingdom
Michele
The price is P23,075
P27,064 total
includes taxes & fees
Sep 13 - Sep 14
The Inn at Stockbridge
Front of property - evening/night

8. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (140 reviews)
"Excellent food and helpful staff"
United States
Richard
The price is P23,810
P26,596 total
includes taxes & fees
Sep 3 - Sep 4
Devonfield Inn B&B
Premium bedding, desk, laptop workspace, blackout drapes

9. Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (120 reviews)
"Terrific host and freshly cooked to order hot breakfast, beautiful grounds, and dog friendly. Would definitely stay again!"
United States
Jamie
The price is P12,242
P13,711 total
includes taxes & fees
Aug 17 - Aug 18
Changing Times Boutique Country Lodging
Property grounds

10. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very Good, (511 reviews)
"Beautiful inn with the most interesting treasures and decorations."
United States
Mary
The price is P9,751
P10,892 total
includes taxes & fees
Sep 1 - Sep 2
Whistler's Inn Bed & Breakfast
Free daily continental breakfast

11. Inn at Pine Plains

Inn at Pine Plains
3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (313 reviews)
"Great stay"
United Kingdom
Katherine
The price is P16,832
P19,042 total
includes taxes & fees
Aug 16 - Aug 17
Inn at Pine Plains
Garden

12. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (466 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is P11,813
P12,959 total
includes taxes & fees
Sep 8 - Sep 9
Shaker Mill Inn
Front of property

13. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (384 reviews)
"Location is convenient to walk through downtown Lee and to get to a show at Tanglewood."
United States
Joseph
The price is P16,526
P18,459 total
includes taxes & fees
Sep 13 - Sep 14
Chambery Inn
Aerial view

14. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (113 reviews)
"Very nice hotel."
United States
Erdem
The price is P9,732
P10,900 total
includes taxes & fees
Sep 1 - Sep 2
Inn at Silver Maple Farm
Exterior

15. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"The entire staff was amazing and the inn was beautiful, we will definitely be back"
United States
Edward
The price is P10,886
P12,525 total
includes taxes & fees
Aug 25 - Aug 26
The Cornell Inn, Lenox & The Berkshires
Premium bedding, iron/ironing board, WiFi (free), individually decorated

16. 33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (75 reviews)
"This was our second stay at 33 Main. Wonderfully maintain, homey environment, with friendly, welcoming and helpful staff. Welcoming cookies, and beautiful water bottle. They even remembered that we asked for the beach and gave us excellent recommendation. Convenient parking in the back. My only suggestion for improvement is breakfast - last year it was much better."
United States
Tatyana
The price is P40,563
P45,308 total
includes taxes & fees
Aug 31 - Sep 1
33 Main
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Sheffield Hotel Reviews

Little Cat Lodge

Little Cat Lodge

10/10 Excellent
"Absolutely love this place! Can’t wait to come back."
Jolie 1-night trip
Posted less than an hour ago
Little Cat Lodge

Find out more about Sheffield

Sheffield B&B information

Number of reviews
3,699
Accommodation
30 B&B
Lowest Price
P7,391
Highest Price
P45,308

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. 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 heart of downtown.Chambery Inn: 9 rooms. Located 14.7 mi (23.7 km) from the core of Sheffield. Enjoy the private yard and deli.
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 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?
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.

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