A lakeside town with autumn foliage, a bridge, and a rocky shoreline.

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Check prices for these dates

Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov
In one month
20 Nov - 22 Nov
In two months
18 Dec - 20 Dec

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, (72 reviews)
"Clean, cozy, and charming. The breakfast is delicious and all went smoothly."
United States
Liliana
The price is SAR 615
SAR 687 total
includes taxes & fees
29 Oct - 30 Oct
Wilder House Berkshires
A sign for 'The Logust Tree Bed & Breakfast' with a contact number.

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, (452 reviews)
"Wonderful stay, and wonderful breakfast."
United States
Daniel
The price is SAR 394
SAR 453 total
includes taxes & fees
21 Oct - 22 Oct
Locust Tree Bed and Breakfast LLC
A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

3. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (238 reviews)
"Quiet room Wonderful breakfast Pleasant atmosphere"
United States
Donna
The price is SAR 627
SAR 721 total
includes taxes & fees
8 Nov - 9 Nov
Blackberry River Inn
A dining table with pastries, a coffee pot, and a vase of sunflowers.

4. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (109 reviews)
"We loved everything about Granville House, especially the innkeepers! Wonderful atmosphere and excellent food! It was definitely the highlight of our trip to New England."
United States
Cynthia
The price is SAR 953
SAR 1,065 total
includes taxes & fees
25 Oct - 26 Oct
Granville House
A patio with a round metal table, a glass of white wine, and a red umbrella.

5. 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 SAR 1,192
SAR 1,323 total
includes taxes & fees
21 Oct - 22 Oct
Manor House Inn
A two-story house with a brick entrance and a white facade.

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, (120 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is SAR 1,404
SAR 1,699 total
includes taxes & fees
7 Nov - 8 Nov
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
9.6 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 SAR 1,369
SAR 1,605 total
includes taxes & fees
1 Nov - 2 Nov
The Inn at Stockbridge
A wooden deck with a table and chairs, surrounded by a metal railing, overlooking a lush green landscape with trees.

8. The Red Door B&B

The Red Door B&B
3.0 star property
Lee
10.0 out of 10, Exceptional, (5 reviews)
"Centrally located. Lovely hosts. Only three bedrooms so we got to know the other guests. The breakfasts were works of art as well as delicious."
United States
Anonymous traveler
The price is SAR 659
SAR 1,050 total
includes taxes & fees
26 Oct - 27 Oct
The Red Door B&B
A large, two-story house with a well-maintained lawn and a fence.

9. 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 SAR 1,385
SAR 1,547 total
includes taxes & fees
2 Nov - 3 Nov
Devonfield Inn B&B
A two-story building with a sign reading "Chambéry Inn".

10. 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 SAR 871
SAR 973 total
includes taxes & fees
28 Oct - 29 Oct
Chambery Inn
A breakfast table with a teapot, milk, and a bagel, set against a brick wall with a framed picture above.

11. Inn at Pine Plains

Inn at Pine Plains
3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (318 reviews)
"good location/ walkable to down town !"
United States
teresina
The price is SAR 1,011
SAR 1,144 total
includes taxes & fees
1 Nov - 2 Nov
Inn at Pine Plains
A red building with a sign reading "Shaker Mill Inn."

12. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (481 reviews)
"Loved the location, fireplace and vibe"
United States
Mahadeva
The price is SAR 465
SAR 510 total
includes taxes & fees
3 Nov - 4 Nov
Shaker Mill Inn
An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

13. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (118 reviews)
"Perfect location for hiking, hanging out and Tanglewood Comfortable and charming common space and cozy nicely decorated rooms Generous breakfast and snacks throughout the day We’ll be back"
United States
Linda
The price is SAR 765
SAR 857 total
includes taxes & fees
1 Nov - 2 Nov
Inn at Silver Maple Farm
A bedroom with a large mural of a waterfall, two bedside lamps, a bed with multiple pillows, and a nightstand with a lamp.

14. 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 SAR 750
SAR 840 total
includes taxes & fees
21 Oct - 22 Oct
Changing Times Boutique Country Lodging
A snow-covered outdoor area with a patio, seating, and a covered dining area.

15. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,004 reviews)
"Lovely room, comfortable bed and a nice breakfast."
United Kingdom
judith
The price is SAR 576
SAR 660 total
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
A garden with a white gazebo, a brick pathway, and various plants and flowers.

16. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (520 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
The price is SAR 554
SAR 619 total
includes taxes & fees
22 Oct - 23 Oct
Whistler's Inn Bed & Breakfast
A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

17. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is SAR 1,198
SAR 1,567 total
includes taxes & fees
20 Nov - 21 Nov
Experience Timeless Elegance in The Edith Wharton Room!
A porch with a white railing, a potted plant, and a view of a garden.

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 SAR 1,319
SAR 1,709 total
includes taxes & fees
20 Nov - 21 Nov
Cozy Carriage House room with a double bed and private balcony
A well-appointed bedroom with a large bed, a bedside table, a chair, and a bathroom visible through an open door.

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 SAR 1,198
SAR 1,567 total
includes taxes & fees
20 Nov - 21 Nov
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
A wooden deck with Adirondack chairs and a small table, leading to a garden area with a swing set.

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

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is SAR 1,379
SAR 1,787 total
includes taxes & fees
20 Nov - 21 Nov
Historic Susan B. Anthony Room - Cozy & Charming Stay
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

10/10 Excellent
"Clean room. Comfortable beds. Good breakfast. Staff were nice and professional."
Melissa 1-night trip
Posted 1 hour ago
Hampton Inn & Suites Berkshires-Lenox

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 Suter Farm and Ashley House 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.