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Check prices for these dates

Next weekend
5 Sept - 7 Sept
In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct

Featured B&B in Sheffield

The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1002)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is AU$280
includes taxes & fees
4 Sept - 5 Sept
The Cornell Inn, Lenox & The Berkshires
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (127)
"We had a vey clean room with a comfortable bed The breakfast was awesome as was the entire staff. Enjoyed our stay"
The price is AU$291
includes taxes & fees
8 Sept - 9 Sept
Blackberry River Inn
Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (401)
"Peaceful area and great staff; Thank you for the service and experience "
The price is AU$186
includes taxes & fees
8 Sept - 9 Sept
Locust Tree Bed and Breakfast LLC
Inn at Pine Plains
Free daily continental breakfast

Inn at Pine Plains

3.5 star property
9.8 out of 10, Exceptional, (291)
"Beautiful place. Accomadating staff. A lovely place to stay"
Inn at Pine Plains
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (482)
"Nice quaint out of the ordinary vacation experience. "
The price is AU$282
includes taxes & fees
27 Aug - 28 Aug
Whistler's Inn Bed & Breakfast
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (422)
"Very casual and easy check in and out; lovely and substantial breakfast"
The price is AU$291
includes taxes & fees
27 Aug - 28 Aug
Shaker Mill Inn
Inn at Silver Maple Farm
Aerial view

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (91)
"What a wonderful one-night stay on the July 4th weekend. It’s a beautiful, comfortable inn with lovely hosts. Also in a great location, set back from a fairly busy country road with several good food options nearby, and charming villages and towns to tour. Highly recommend. "
The price is AU$361
includes taxes & fees
2 Sept - 3 Sept
Inn at Silver Maple Farm
Brook Farm Inn
Loft, Private Bathroom (Skylight Loft)

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (159)
"Inn was gorgeous and staff exceptional!"
Brook Farm Inn
Wilder House Berkshires
Wilder House Berkshires Room 3

Wilder House Berkshires

2.0 star property
9.6 out of 10, Exceptional, (29)
"Brads and Lara both served a fabulous breakfast. So friendly and welcoming! The bed was very comfortable. Only complaint was that the cabinet, closet door needs to be greased with WD 40 please on the hinges! A terrible & loud screeching noise!"
The price is AU$276
includes taxes & fees
10 Sept - 11 Sept
Wilder House Berkshires
Tanglewood Suites
2 Bedrooms 1 Bath

Tanglewood Suites

2.5 star property
7.2 out of 10, Good, (19)
"The owner did not honor our confirmed Expedia reservation, so we had to find a hotel at the last minute. She made up various excuses and was very rude."
The price is AU$415
includes taxes & fees
27 Aug - 28 Aug
Tanglewood Suites
Lakehouse Inn
Porch

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (277)
"Great Views & Hospitality"
Lakehouse Inn
Granville House
Individually decorated, individually furnished, desk, laptop workspace

Granville House

3.0 star property
10.0 out of 10, Exceptional, (84)
"Phenomenal hospitality, eclectic decor, luxurious sleep - we have been raving about our stay and will definitely be back!"
The price is AU$428
includes taxes & fees
7 Sept - 8 Sept
Granville House
Changing Times Boutique Country Lodging
Porch

Changing Times Boutique Country Lodging

3.5 star property
10.0 out of 10, Exceptional, (103)
"The b and b is charming and comfortable. Loretta was extremely welcoming and accommodating."
The price is AU$302
includes taxes & fees
2 Sept - 3 Sept
Changing Times Boutique Country Lodging
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (369)
"ease of late check in. Super comfortable room."
Chambery Inn
Jenny's Country Manor
Exterior

Jenny's Country Manor

2.0 star property
7.6 out of 10, Good, (130)
"The paint job could be redone and the stair are a bit hazardous. The bath facilities could be improved."
The price is AU$244
includes taxes & fees
8 Sept - 9 Sept
Jenny's Country Manor
33 Main
Luxury Room, 1 King Bed, Bathtub

33 Main

4.0 star property
10.0 out of 10, Exceptional, (70)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
The price is AU$970
includes taxes & fees
2 Sept - 3 Sept
33 Main
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business centre

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is AU$577
includes taxes & fees
8 Sept - 9 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Manor House Inn
Interior detail

Manor House Inn

3.0 star property
9.2 out of 10, Wonderful, (137)
"Excellent bed and breakfast, room was clean and comfortable."
The price is AU$421
includes taxes & fees
27 Aug - 28 Aug
Manor House Inn
Inn at Kenmore Hall
Lobby

Inn at Kenmore Hall

3.0 star property
10.0 out of 10, Exceptional, (27)
"This is a beautiful property straight out of a magazine. Service was impeccable"
Inn at Kenmore Hall
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 Constance by the Lenox Collection

The Constance by the Lenox Collection

10/10 Excellent
"We enjoyed our stay at the Whitlock (part of the same management as the Constance). Good restaurants easy to walk to. Quiet. Only thing we missed was a comfortable armchair in the bedroom."
James 1-night trip
Posted 1 day ago
The Constance by the Lenox Collection

Find out more about Sheffield

Find out more about Sheffield

Sheffield B&B information

Number of reviews
3,643
Accommodation
40 B&B
Lowest Price
AU$186
Highest Price
AU$970

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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, Mount Everett State Reservation and Thom Reed UFO Monument Park 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. Chambery Inn: 9 rooms. Located 14.7 mi (23.7 km) from the core of Sheffield. Enjoy the private garden and snack bar/deli.
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 Mount Everett State Reservation are some notable spots. You should put Magnolia Bluffs Casino and Three Mile Pond Wildlife Management Area 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.