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

Find a Bed and Breakfast in Sheffield from CA $169

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Check prices for these dates

Next weekend
Aug 14 - Aug 16
In two weeks
Aug 21 - Aug 23
In one month
Sep 4 - Sep 6
In two months
Oct 2 - Oct 4

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, (59 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is CA $249
CA $278 total
includes taxes & fees
Aug 9 - Aug 10
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, (437 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 CA $147
CA $169 total
includes taxes & fees
Aug 10 - Aug 11
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, (200 reviews)
"Excellent breakfast, very nice staff."
United States
Leslie
The price is CA $245
CA $282 total
includes taxes & fees
Aug 12 - Aug 13
Blackberry River Inn
Front of property

4. 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 CA $429
CA $476 total
includes taxes & fees
Aug 31 - Sep 1
Manor House Inn
Desk, laptop workspace, iron/ironing board (on request), WiFi (free)

5. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (102 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 CA $386
CA $431 total
includes taxes & fees
Aug 19 - Aug 20
Granville House
Front of property - evening/night

6. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (139 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is CA $546
CA $610 total
includes taxes & fees
Sep 3 - Sep 4
Devonfield Inn B&B
Front of property

7. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (383 reviews)
"Location is convenient to walk through downtown Lee and to get to a show at Tanglewood."
United States
Joseph
The price is CA $379
CA $423 total
includes taxes & fees
Sep 3 - Sep 4
Chambery Inn
Suite, Private Bathroom (RedBird Suite) | View from room

8. 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 CA $463
CA $560 total
includes taxes & fees
Aug 24 - Aug 25
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property

9. 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 CA $570
CA $669 total
includes taxes & fees
Aug 12 - Aug 13
The Inn at Stockbridge
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, (509 reviews)
"Beautiful inn with the most interesting treasures and decorations."
United States
Mary
The price is CA $236
CA $264 total
includes taxes & fees
Aug 5 - Aug 6
Whistler's Inn Bed & Breakfast
Aerial view

11. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (112 reviews)
"Very nice hotel."
United States
Erdem
The price is CA $265
CA $297 total
includes taxes & fees
Sep 3 - Sep 4
Inn at Silver Maple Farm
Garden

12. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (465 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is CA $238
CA $261 total
includes taxes & fees
Aug 5 - Aug 6
Shaker Mill Inn
1 bedroom, WiFi, bed sheets

13. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is CA $437
CA $571 total
includes taxes & fees
Aug 25 - Aug 26
Experience Timeless Elegance in The Edith Wharton Room!
Exterior

14. 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 CA $278
CA $319 total
includes taxes & fees
Aug 31 - Sep 1
The Cornell Inn, Lenox & The Berkshires
Luxury Room, 1 King Bed, Bathtub

15. 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 CA $967
CA $1,080 total
includes taxes & fees
Aug 23 - Aug 24
33 Main
Free daily continental breakfast

16. Inn at Pine Plains

Inn at Pine Plains
3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (312 reviews)
"Great stay"
United Kingdom
Katherine
The price is CA $375
CA $424 total
includes taxes & fees
Aug 12 - Aug 13
Inn at Pine Plains
Terrace/patio

17. Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is CA $505
CA $661 total
includes taxes & fees
Aug 20 - Aug 21
Historic Susan B. Anthony Room - Cozy & Charming Stay
Deluxe Room, 1 King Bed, Ensuite (2nd Floor)

18. Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (119 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 CA $280
CA $314 total
includes taxes & fees
Aug 5 - Aug 6
Changing Times Boutique Country Lodging
3 bedrooms, bed sheets

19. Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is CA $437
CA $571 total
includes taxes & fees
Aug 25 - Aug 26
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
1 bedroom, bed sheets

20. Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Lenox
The price is CA $606
CA $792 total
includes taxes & fees
Aug 31 - Sep 1
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
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

Berkshires Untold

Berkshires Untold

8/10 Good
"This is a remodeled and upgraded Motel with a new look and outfit. The rooms are recently renovated with new bathrooms, beds, and AC. Everything is clean and easily accessible, parking is in front of the door. The main building has a bar with a seating area, and there is a patio with couches and gas fire pits. One can hear the traffic from route 7, though the windows block most of the noise in the rooms. We appreciated the bar and the menu which offered a variety of drinks and food choices. The staff was very nice and accommodating, particularly, the bartender, This is a great place for a short stay over, a combination of Motel with hotel-like service to hang out with drinks and food. Highly recommended."
Kai 1-night trip
Posted less than an hour ago
Berkshires Untold

Find out more about Sheffield

Sheffield B&B information

Number of reviews
1,973
Accommodation
41 B&B
Lowest Price
CA $169
Highest Price
CA $1,080

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.Shaker Mill Inn: 9 rooms. Located 15.6 mi (25.1 km) from the core of Sheffield.
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 Suter Farm 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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