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Check prices for these dates

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

Our top choices for Sheffield bed & breakfast

Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (49 reviews)
"the breakfast is from heaven. the house is beautiful. love the stay."
United States
Catherine
The price is AU$272
includes taxes & fees
31 May - 1 June
Wilder House Berkshires
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (457 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is AU$154
includes taxes & fees
26 May - 27 May
Shaker Mill Inn
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (183 reviews)
"beautiful inn"
United States
Maura
The price is AU$229
includes taxes & fees
31 May - 1 June
Blackberry River Inn
Front of property

Manor House Inn

Manor House Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (138 reviews)
"Excellent bed and breakfast, room was clean and comfortable."
United States
Kevin
The price is AU$466
includes taxes & fees
16 June - 17 June
Manor House Inn
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (376 reviews)
"Yes the room was spotless and always the staff is ready to answer any questions that we might have. We have been enjoying the Chambery Inn for many years always had a great stay and again looking for our next visit. Vincent Farricielli and Roibert Modena. "
United States
robert
The price is AU$268
includes taxes & fees
27 May - 28 May
Chambery Inn
Exterior

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
9.8 out of 10, Exceptional, (6 reviews)
"The new owners have done a great job. The place is immaculate, the room was very comfortable and well appointed, the common areas charming. Highly recommended."
United States
Robert
The price is AU$388
includes taxes & fees
27 May - 28 May
The Berkshire Mountain Inn
Front of property – evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (138 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is AU$516
includes taxes & fees
27 May - 28 May
Devonfield Inn B&B
Individually decorated, individually furnished, desk, laptop workspace

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (101 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 AU$431
includes taxes & fees
1 June - 2 June
Granville House
Property grounds

Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (501 reviews)
"This family owned Inn is absolutely charming and the owners are so nice! I will definitely stay here again when I visit the Berkshires."
United States
Stacey
The price is AU$416
includes taxes & fees
26 May - 27 May
Whistler's Inn Bed & Breakfast
Suite, Private Bathroom (RedBird Suite) | View from room

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, (111 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is AU$560
includes taxes & fees
7 June - 8 June
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Luxury Room, 1 King Bed, Bathtub

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is AU$944
includes taxes & fees
31 May - 1 June
33 Main
Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (417 reviews)
"Clean, good breakfast, friendly staff"
United States
Debra
The price is AU$169
includes taxes & fees
29 May - 30 May
Locust Tree Bed and Breakfast LLC
Aerial view

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (107 reviews)
"Very nice hotel."
United States
Erdem
The price is AU$266
includes taxes & fees
23 June - 24 June
Inn at Silver Maple Farm
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,005 reviews)
"enjoy your vacation"
United States
lev
The price is AU$239
includes taxes & fees
9 June - 10 June
The Cornell Inn, Lenox & The Berkshires
1 bedroom, WiFi, bed sheets, wheelchair access

Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is AU$456
includes taxes & fees
26 May - 27 May
Experience Timeless Elegance in The Edith Wharton Room!
Free daily continental breakfast

Inn at Pine Plains

Inn at Pine Plains
3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (306 reviews)
"Great stay"
United Kingdom
Katherine
The price is AU$423
includes taxes & fees
26 May - 27 May
Inn at Pine Plains
Deluxe Room, 1 King Bed, Ensuite (2nd Floor)

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (117 reviews)
"The place is so authentic and beautiful, the owner is so kind and friendly, and we had really good experience "
United States
Tamir
The price is AU$306
includes taxes & fees
26 May - 27 May
Changing Times Boutique Country Lodging
Lobby

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
Richmond
10.0 out of 10, Exceptional, (28 reviews)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is AU$654
includes taxes & fees
16 June - 17 June
Inn at Kenmore Hall
Interior

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 AU$556
includes taxes & fees
8 June - 9 June
Elegant Carriage House room with a queen bed and private patio.
Interior

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 AU$535
includes taxes & fees
31 May - 1 June
Cozy Carriage House room with a double bed and private balcony
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

10/10 Excellent
"Had a great stay at the Yankee Inn. I would definitely stay here again. Check in was great and super helpful for what to do and eat in the area. Carl at the bar was the best! Only complaint is that the fitted sheet kept coming up from our king mattress I had the fix them multiple times. Nice indoor pool and hot tub. Close to a lot."
Stacey 1-night trip
Posted 14 hours ago
The Yankee Inn

Find out more about Sheffield

Sheffield B&B information

Number of reviews
3,336
Accommodation
41 B&B
Lowest Price
AU$154
Highest Price
AU$944

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. Locust Tree Bed and Breakfast LLC: 7 rooms. Situated 6.8 mi (11 km) from the heart of Sheffield. Shaker Mill Inn: 9 rooms. 15.6 mi (25.1 km) from the city centre. Blackberry River Inn: 14 rooms. Located 9.2 mi (14.9 km) from the core of Sheffield. Enjoy the free cooked breakfast and outdoor pool.
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 Magnolia Bluffs Casino 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?
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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