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

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Check prices for these dates

Next weekend
28 Aug - 30 Aug
In two weeks
4 Sept - 6 Sept
In one month
18 Sept - 20 Sept
In two months
16 Oct - 18 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, (62 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is €194
includes taxes & fees
27 Aug - 28 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, (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 €103
includes taxes & fees
26 Aug - 27 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, (208 reviews)
"Breakfast is great!"
United States
Cheryl
The price is €187
includes taxes & fees
23 Aug - 24 Aug
Blackberry River Inn
Desk, laptop workspace, iron/ironing board (on request), free WiFi

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 €263
includes taxes & fees
26 Aug - 27 Aug
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 €313
includes taxes & fees
31 Aug - 1 Sept
Manor House Inn
Suite, Private Bathroom (RedBird Suite) | 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 €342
includes taxes & fees
7 Sept - 8 Sept
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, (103 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 €379
includes taxes & fees
13 Sept - 14 Sept
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 €372
includes taxes & fees
3 Sept - 4 Sept
Devonfield Inn B&B
Deluxe Room, 1 King Bed, Ensuite (2nd Floor)

9. Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (122 reviews)
"A great place to stay!"
United States
Thomas
The price is €192
includes taxes & fees
31 Aug - 1 Sept
Changing Times Boutique Country Lodging
Front of property

10. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (386 reviews)
"The room was clean and very quiet. Breakfast was delivered to our room as requested."
United States
Richard
The price is €258
includes taxes & fees
23 Aug - 24 Aug
Chambery Inn
Property grounds

11. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (515 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
The price is €152
includes taxes & fees
13 Sept - 14 Sept
Whistler's Inn Bed & Breakfast
Garden

12. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (467 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is €170
includes taxes & fees
8 Sept - 9 Sept
Shaker Mill Inn
Free daily continental breakfast

13. 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 €266
includes taxes & fees
23 Aug - 24 Aug
Inn at Pine Plains
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 €133
includes taxes & fees
25 Aug - 26 Aug
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, (1,007 reviews)
"The entire staff was amazing and the inn was beautiful, we will definitely be back"
United States
Edward
The price is €194
includes taxes & fees
24 Aug - 25 Aug
The Cornell Inn, Lenox & The Berkshires
1 bedroom, WiFi, bed sheets

16. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is €349
includes taxes & fees
24 Aug - 25 Aug
Experience Timeless Elegance in The Edith Wharton Room!
Luxury Room, 1 King Bed, Bathtub

17. 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 €634
includes taxes & fees
3 Sept - 4 Sept
33 Main
Interior

18. Elegant Carriage House room with a queen bed and private patio.

Elegant Carriage House room with a queen bed and private patio.
Lenox
The price is €366
includes taxes & fees
8 Sept - 9 Sept
Elegant Carriage House room with a queen bed and private patio.
Interior

19. Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony
Lenox
The price is €382
includes taxes & fees
31 Aug - 1 Sept
Cozy Carriage House room with a double bed and private balcony
3 bedrooms, bed sheets

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is €349
includes taxes & fees
24 Aug - 25 Aug
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
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

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

8/10 Good
"The staff were all very nice and polite."
ella 1-night trip
Posted 5 hours ago
Hampton Inn & Suites Berkshires-Lenox

Find out more about Sheffield

Sheffield B&B information

Number of reviews
3,197
Accommodation
41 B&B
Lowest Price
€103
Highest Price
€634

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.
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 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.