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Our top choices for Sheffield hotels

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (42 reviews)
"It was a very pleasant hybrid of a classic BnB with the privacy of an air BnB. Host was on point and communicative. We loved hanging out downstairs in the living room(s). Breakfast was fabulous "
United States
Evan M
Wilder House Berkshires

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (723 reviews)
"Always love staying here. The staff is fantastic, amenities are great, and the breakfast is just lovely. Will be returning soon!"
United States
Domenic
The price is AU$143
includes taxes & fees
22 Jan - 23 Jan
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (18 reviews)
"It was clean and environment is relaxing."
United States
KEYA
The price is AU$336
includes taxes & fees
27 Jan - 28 Jan
Prospect Berkshires

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (134 reviews)
"We loved our stay at Gedney. Michael was a sweetheart, and the grounds are GORGEOUS. We loved our room with fireplace - the whole setting is just country and updated/old. For anyone who loves farms and barns and rustic, this is for you. Can't wait to return."
United States
Lynda
The price is AU$303
includes taxes & fees
27 Jan - 28 Jan
Gedney Farm

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (763 reviews)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is AU$251
includes taxes & fees
25 Jan - 26 Jan
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very good, (1,002 reviews)
"Great place to stay for a night in Great Barrington. Walk to everything in town "
United States
robert
The price is AU$118
includes taxes & fees
5 Feb - 6 Feb
Quality Inn Great Barrington

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (90 reviews)
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is AU$548
includes taxes & fees
1 Feb - 2 Feb
The Old Inn On The Green

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (414 reviews)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is AU$180
includes taxes & fees
21 Jan - 22 Jan
Locust Tree Bed and Breakfast LLC

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (817 reviews)
"Unbelieveably clean for the price."
United States
Micah
Monument Mountain Motel

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (37 reviews)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
The price is AU$216
includes taxes & fees
27 Jan - 28 Jan
East Rock Inn

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.0 out of 10, Very good, (12 reviews)
"Antonia was wonderful and made our stay special. She was kind and warm and when we were initially unhappy with our room immediately rectified the situation and in the end our stay was perfect! It’s a charming hotel, clean and centrally located, walking distance to all the local shops in town."
United States
Jamie
The price is AU$272
includes taxes & fees
25 Jan - 26 Jan
The Millerton Inn

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (74 reviews)
"Very clean and friendly staff that go above and beyond for their guests even in a snow storm! "
United States
Kira
The price is AU$213
includes taxes & fees
29 Jan - 30 Jan
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (566 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is AU$125
includes taxes & fees
1 Feb - 2 Feb
Travelodge by Wyndham Great Barrington Berkshires

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (549 reviews)
"Perfect for pets "
United States
Maria
The price is AU$183
includes taxes & fees
1 Feb - 2 Feb
The Little Lion

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (167 reviews)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is AU$282
includes taxes & fees
26 Jan - 27 Jan
Blackberry River Inn

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (816 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is AU$198
includes taxes & fees
1 Feb - 2 Feb
Berkshire Mountain Lodge

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164 reviews)
"Everything was perfect - location and accommodation."
United States
Christopher
Brook Farm Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (443 reviews)
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
The price is AU$170
includes taxes & fees
26 Jan - 27 Jan
Shaker Mill Inn

Cornwall Inn and Lodge

Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (156 reviews)
"This inn was very quaint and welcoming. It was a nice inn for the value. "
United States
Jacqueline
The price is AU$363
includes taxes & fees
13 Feb - 14 Feb
Cornwall Inn and Lodge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (16 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is AU$231
includes taxes & fees
1 Feb - 2 Feb
Element Lenox Berkshires
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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Stay near popular Sheffield attractions

Learn more about Sheffield

Tucked in the Berkshires, this charming town offers scenic hikes at Bartholomew's Cobble and local art at the Sheffield Historical Society. Catch live performances at the Berkshire Theatre Festival in nearby Stockbridge or sample farm-fresh produce at the weekend farmers' market on the town green.

FTYTP1 The Upper Sheffield Covered Bridge, Sheffield, Massachusetts, USA

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Frequently asked questions

Where is the best place to stay in Sheffield?
Wilder House Berkshires is one of the top choices for your stay based on our traveller data. This B&B offers free breakfast and free parking. Two other options for your trip to the area are Berkshire Mountain Lodge and The Yankee, Trademark Collection by Wyndham. See all available top hotels, or vacation rentals in Sheffield.
What are some of the best holiday rentals that Sheffield has to offer?
Peace and quiet on the lake: This holiday home rental outside of Sheffield is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind. See all vacation rentals in Sheffield.
If I need to cancel my hotel reservation in Sheffield, will I receive a refund?
Yes, the majority of hotel reservations are fully refundable provided that you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If your reservation is non-refundable, it may still be possible to cancel it and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Sheffield.
What are some accommodation options with pools in Sheffield?
Berkshire Mountain Lodge: Features free self parking, an indoor pool and complimentary wireless Internet access. The Yankee, Trademark Collection by Wyndham and Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG are a couple of other choices that feature an on-site pool. View all hotels with pools in Sheffield.
What's it like staying in Sheffield?
Visitors can enjoy all that Sheffield has to offer, including the casinos and local tours. In Sheffield, there are 32 hotels and other accommodation options to choose from. Find out more about Sheffield.
What are the top places to visit in Sheffield?
Favourite places to visit include Magnolia Bluffs Casino, Housatonic River and Drury Preserve. A couple of additional sights to add to your itinerary are Ashley House and Mount Everett State Reservation. Take a look at what more there is to see and do in Expedia's Sheffield guide.
What's the seasonal weather like in Sheffield?
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.

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