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

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Check prices for these dates

Next weekend
6 Nov - 8 Nov
In two weeks
13 Nov - 15 Nov
In one month
27 Nov - 29 Nov
In two months
25 Dec - 27 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 RM670
RM748 total
includes taxes & fees
29 Oct - 30 Oct
Wilder House Berkshires
A covered porch with white railings and rocking chairs.

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, (453 reviews)
"Wonderful stay, and wonderful breakfast."
United States
Daniel
The price is RM429
RM494 total
includes taxes & fees
29 Oct - 30 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, (250 reviews)
"Great Breakfast Bed was okay Room very quaint hotel was very nice inside"
United States
Melanie
The price is RM777
RM893 total
includes taxes & fees
29 Oct - 30 Oct
Blackberry River Inn
A dining area with a round table and four chairs, a radiator, and a window with a view of greenery.

4. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (110 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 RM1,042
RM1,164 total
includes taxes & fees
5 Nov - 6 Nov
Granville House
A two-story house with a brick entrance and a white facade.

5. 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 RM1,561
RM1,889 total
includes taxes & fees
11 Nov - 12 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A snow-covered outdoor area with a patio, seating, and a covered dining area.

6. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.4 out of 10, Exceptional, (1,000 reviews)
"Lovely room, comfortable bed and a nice breakfast."
United Kingdom
judith
The price is RM695
RM797 total
includes taxes & fees
1 Nov - 2 Nov
The Cornell Inn, Lenox & The Berkshires
Front of property

7. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (108 reviews)
"Wonderful place… clean, cosy room, comfy bed, friendly staff, great breakfast. Delightful location near Norman Rockwell museum."
United States
Kimberly
The price is RM1,491
RM1,749 total
includes taxes & fees
12 Nov - 13 Nov
The Inn at Stockbridge
An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

8. 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 RM752
RM842 total
includes taxes & fees
22 Nov - 23 Nov
Inn at Silver Maple Farm
A breakfast table with a teapot, milk, and a bagel, set against a brick wall with a framed picture above.

9. 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 RM1,124
RM1,272 total
includes taxes & fees
29 Oct - 30 Oct
Inn at Pine Plains
A wooden deck with a table and chairs, surrounded by a metal railing, overlooking a lush green landscape with trees.

10. 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 traveller
The Red Door B&B
A garden with a white gazebo, a brick pathway, and various plants and flowers.

11. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (521 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
The price is RM563
RM629 total
includes taxes & fees
29 Oct - 30 Oct
Whistler's Inn Bed & Breakfast
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, (482 reviews)
"Loved the location, fireplace and vibe"
United States
Mahadeva
The price is RM458
RM502 total
includes taxes & fees
2 Nov - 3 Nov
Shaker Mill Inn
A bedroom with a large mural of a waterfall, two bedside lamps, a bed with multiple pillows, and a nightstand with a lamp.

13. 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 RM818
RM916 total
includes taxes & fees
9 Nov - 10 Nov
Changing Times Boutique Country Lodging
A large, two-story house with a well-maintained lawn and a fence.

14. 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 RM1,508
RM1,685 total
includes taxes & fees
2 Nov - 3 Nov
Devonfield Inn B&B
A two-story building with a sign reading "Chambéry Inn".

15. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (390 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 RM1,104
RM1,233 total
includes taxes & fees
29 Oct - 30 Oct
Chambery Inn
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

16. Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (178 reviews)
"Breakfast was not only delicious, the room was sweet and bright and staff very attentive."
United States
Carrie
The price is RM795
RM921 total
includes taxes & fees
2 Nov - 3 Nov
Brook Farm 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

The Yankee Inn

The Yankee Inn

8/10 Good
"We stayed at the Yankee Inn for 1 night. We had no problems with check-in. Our room was clean but outdated except the bathroom which was very nice. Good water pressure in the shower and the bed was comfortable. Unfortunately, due to myself not feeling well, we did not use the hot tub, enjoy the fire pit or try breakfast all of which would have likely improved our stay. Maybe next time!"
Jeanne 1-night trip
Posted 3 hours ago
The Yankee Inn

Find out more about Sheffield

Sheffield B&B information

Number of reviews
3,028
Accommodation
30 B&B
Lowest Price
RM494
Highest Price
RM1,889

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 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?
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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