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

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Check prices for these dates

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

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 Rp3.196.261
Rp3.570.224 total
includes taxes & fees
9 Aug - 10 Aug
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 Rp1.889.685
Rp2.173.138 total
includes taxes & fees
10 Aug - 11 Aug
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 Rp3.419.430
Rp3.932.345 total
includes taxes & fees
11 Aug - 12 Aug
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 Rp5.929.238
Rp6.581.454 total
includes taxes & fees
31 Aug - 1 Sept
Manor House Inn
Desk, laptop workspace, iron/ironing board (on request), free WiFi

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 Rp4.956.050
Rp5.535.998 total
includes taxes & fees
17 Aug - 18 Aug
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 Rp7.000.833
Rp7.819.876 total
includes taxes & fees
3 Sept - 4 Sept
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 Rp4.865.778
Rp5.435.073 total
includes taxes & fees
10 Aug - 11 Aug
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 Rp5.942.069
Rp7.188.180 total
includes taxes & fees
26 Aug - 27 Aug
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 Rp7.321.180
Rp8.586.729 total
includes taxes & fees
25 Aug - 26 Aug
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 Rp3.000.663
Rp3.351.732 total
includes taxes & fees
9 Aug - 10 Aug
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 Rp3.401.433
Rp3.809.605 total
includes taxes & fees
3 Sept - 4 Sept
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 Rp4.247.292
Rp4.659.279 total
includes taxes & fees
10 Aug - 11 Aug
Shaker Mill Inn
Exterior

13. 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 Rp3.561.436
Rp4.097.468 total
includes taxes & fees
25 Aug - 26 Aug
The Cornell Inn, Lenox & The Berkshires
Luxury Room, 1 King Bed, Bathtub | Premium bedding, iron/ironing board, free WiFi, individually decorated

14. 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 Rp13.251.551
Rp14.801.982 total
includes taxes & fees
3 Sept - 4 Sept
33 Main
Free daily continental breakfast

15. 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 Rp4.949.175
Rp5.598.755 total
includes taxes & fees
2 Sept - 3 Sept
Inn at Pine Plains
Deluxe Room, 1 King Bed, Ensuite (2nd Floor) | Premium bedding, desk, laptop workspace, blackout curtains

16. 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 Rp3.599.400
Rp4.031.328 total
includes taxes & fees
2 Sept - 3 Sept
Changing Times Boutique Country Lodging
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
"Such a sweet hotel in a pretty spot!"
Jane 1-night trip
Posted 3 hours ago
Little Cat Lodge

Find out more about Sheffield

Sheffield B&B information

Number of reviews
1,973
Accommodation
30 B&B
Lowest Price
Rp2.173.138
Highest Price
Rp14.801.982

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