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

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Check prices for these dates

Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct
In one month
23 Oct - 25 Oct
In two months
20 Nov - 22 Nov

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, (67 reviews)
"Perfect little b&b."
United States
Mark
The price is AED 687
AED 767 total
includes taxes & fees
27 Sep - 28 Sep
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, (448 reviews)
"The whole vibe of the B&B was so simple and perfect. 10/10 will stay again."
United States
Nicholas
The price is AED 386
AED 444 total
includes taxes & fees
27 Sep - 28 Sep
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, (222 reviews)
"Great breakfast"
United States
Brian
The price is AED 468
AED 539 total
includes taxes & fees
27 Sep - 28 Sep
Blackberry River Inn
Front of property

4. Manor House Inn

Manor House Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (141 reviews)
"Excellent bed and breakfast, room was clean and comfortable."
United States
Kevin
The price is AED 1,158
AED 1,285 total
includes taxes & fees
28 Sep - 29 Sep
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, (106 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 AED 823
AED 919 total
includes taxes & fees
27 Sep - 28 Sep
Granville House
Front of property

6. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (388 reviews)
"An absolutely perfect getaway spot! Beautiful rooms, great service, and an ideal location. Highly recommend and we will be going back."
United States
Alexandra
The price is AED 992
AED 1,108 total
includes taxes & fees
27 Sep - 28 Sep
Chambery Inn
Front of property - evening/night

7. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (141 reviews)
"Wonderful location and hosts are amazing. Breakfast was great. Clean."
United States
Sebastien
The price is AED 1,502
AED 1,678 total
includes taxes & fees
25 Oct - 26 Oct
Devonfield Inn B&B
Front of property

8. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (107 reviews)
"Lovely grounds, property.. room was lovely. Delicious breakfast friendly helpful owners and staff great location"
United States
Jodi
The price is AED 1,609
AED 1,887 total
includes taxes & fees
27 Sep - 28 Sep
The Inn at Stockbridge
Property grounds

9. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (518 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
The price is AED 582
AED 650 total
includes taxes & fees
5 Oct - 6 Oct
Whistler's Inn Bed & Breakfast
Suite, Private Bathroom (RedBird Suite) | View from room

10. 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, (118 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is AED 1,612
AED 1,951 total
includes taxes & fees
12 Oct - 13 Oct
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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, (117 reviews)
"We had a very pleasant stay at this. Eautiful country property. Check in was smooth and instructions were easy to follow. Our room, in the main building was well appointed. The bed was super comfortable and the amenities were fine. Breakfast was great! Common areas were lovely and inviting, and the s’mores kits in the lobby were just the thing for an evening around the outdoor fire pit. Highly recommend for anyone seeking a serene country setting."
United States
Jody
The price is AED 786
AED 880 total
includes taxes & fees
28 Sep - 29 Sep
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, (475 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is AED 657
AED 721 total
includes taxes & fees
1 Oct - 2 Oct
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 AED 909
AED 1,124 total
includes taxes & fees
27 Oct - 28 Oct
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, (1,001 reviews)
"Convenient location for Tanglewood and other Berkshire sights. Nice complimentary breakfast and arrival cocktail."
United States
Rosann
The price is AED 564
AED 647 total
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
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, (317 reviews)
"Great place! Comfy and charming!!"
United States
Mary
The price is AED 859
AED 971 total
includes taxes & fees
7 Oct - 8 Oct
Inn at Pine Plains
Deluxe Room, 1 King Bed, Ensuite | Premium bedding, desk, laptop workspace, blackout drapes

16. Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (127 reviews)
"A great place to stay!"
United States
Thomas
The price is AED 735
AED 823 total
includes taxes & fees
28 Sep - 29 Sep
Changing Times Boutique Country Lodging
Terrace/patio

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

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is AED 1,026
AED 1,259 total
includes taxes & fees
27 Sep - 28 Sep
Historic Susan B. Anthony Room - Cozy & Charming Stay
Interior

18. 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 AED 1,291
AED 1,579 total
includes taxes & fees
28 Sep - 29 Sep
Cozy Carriage House room with a double bed and private balcony
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 AED 909
AED 1,124 total
includes taxes & fees
27 Oct - 28 Oct
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Interior

20. 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 AED 1,408
AED 1,722 total
includes taxes & fees
20 Oct - 21 Oct
Elegant Carriage House room with a queen bed and private patio.
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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"If you want a perfect New England experience, this is the place. The hotel is amazing, it’s older so don’t think you’re going to walk into a modern place, but don’t let that deter you, the vibe is great! Will definitely stay here again."
Michelle 2-night trip
Posted less than an hour ago
The Red Lion Inn

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.
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 Ashley House and Mount Everett State Reservation 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.