Find hotels in Sheffield, MA from 2.227.616 ₫

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9 Dec - 10 Dec
Tomorrow
10 Dec - 11 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

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Our top choices for Sheffield hotels

Wilder House Berkshires Room 3 | Premium bedding, individually decorated, individually furnished
Wilder House Berkshires

Wilder House Berkshires

2.0 star property
Sheffield
9.8 out of 10, Exceptional, (38)
"Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you! "
United States
Allison
The price is 4.270.644 ₫
4.770.310 ₫ total
includes taxes & fees
10 Dec - 11 Dec
Wilder House Berkshires
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1008)
"Great stay!"
United States
Ann
The price is 2.352.809 ₫
2.628.088 ₫ total
includes taxes & fees
18 Dec - 19 Dec
The Yankee, Trademark Collection by Wyndham
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
9.0 out of 10, Wonderful, (1006)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is 2.667.834 ₫
2.979.971 ₫ total
includes taxes & fees
21 Dec - 22 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (811)
"Easiest check in and out. Great food in dining room. "
United States
William
The price is 2.890.514 ₫
3.228.704 ₫ total
includes taxes & fees
11 Dec - 12 Dec
Berkshires Untold
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
South Lee
9.0 out of 10, Wonderful, (797)
"Place was great!"
United States
Benjamin
The price is 3.002.746 ₫
3.869.463 ₫ total
includes taxes & fees
11 Dec - 12 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Outdoor pool, pool loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1001)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is 3.980.813 ₫
5.624.546 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
The Red Lion Inn
Front of property
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property
Lenox
9.0 out of 10, Wonderful, (1000)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is 4.404.943 ₫
5.067.931 ₫ total
includes taxes & fees
10 Dec - 11 Dec
The Cornell Inn, Lenox & The Berkshires
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (784)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (65)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is 2.554.478 ₫
2.853.351 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
American cuisine
the Alander

the Alander

2.5 star property
Copake
9.0 out of 10, Wonderful, (187)
"The Alander has such a fun story, and was a great stay. We were just passing through for the night and it had everything we could need! It reminded me of Rosebud Motel group from Schitts Creek ;) if you know you know! Will definitely be staying again!"
United States
Jenna
The price is 3.690.680 ₫
4.133.561 ₫ total
includes taxes & fees
10 Dec - 11 Dec
the Alander
Double Room | Egyptian cotton sheets, premium bedding, memory-foam beds, desk
The Brooks Motel

The Brooks Motel

2.0 star property
Hillsdale
7.4 out of 10, Good, (119)
"Unbearably hard bed, very small room, particle board decor, icy cold cement floor. We checked out within minutes of arriving. "
United States
Carmen
The Brooks Motel
Exterior
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, (706)
"Great hospitality "
United States
regina maria
The price is 2.688.924 ₫
3.003.527 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Front of property
Chambery Inn

Chambery Inn

3.0 star property
Lee
9.6 out of 10, Exceptional, (373)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Library
Blackberry River Inn

Blackberry River Inn

3.0 star property
Norfolk
9.4 out of 10, Exceptional, (163)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is 4.332.595 ₫
4.982.484 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Blackberry River Inn
Egyptian cotton sheets, premium bedding, down duvets, minibar
Prospect Berkshires

Prospect Berkshires

3.0 star property
Egremont
9.6 out of 10, Exceptional, (15)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is 6.854.120 ₫
8.539.442 ₫ total
includes taxes & fees
10 Dec - 11 Dec
Prospect Berkshires
Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 star property
Lenox
9.2 out of 10, Wonderful, (589)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is 3.558.870 ₫
3.975.257 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Courtyard by Marriott Lenox Berkshires
Lobby
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, (758)
"Clean room, very courteous staff "
United States
Thomas
The price is 3.347.974 ₫
3.739.686 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Free daily continental breakfast
Inn at Pine Plains

Inn at Pine Plains

3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (301)
"Great stay"
United Kingdom
Katherine
The price is 6.524.595 ₫
7.380.947 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Inn at Pine Plains
Porch
Interlaken Inn & Resort

Interlaken Inn & Resort

3.5 star property
Lakeville
8.2 out of 10, Very good, (270)
"It is so pretty and the views around the hotel were amazing. "
United States
Noraida
The price is 5.907.724 ₫
6.793.883 ₫ total
includes taxes & fees
10 Dec - 11 Dec
Interlaken Inn & Resort
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
Cornwall Inn and Lodge

Cornwall Inn and Lodge

3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (155)
"This inn was very quaint and welcoming. It was a nice inn for the value. "
United States
Jacqueline
The price is 5.578.199 ₫
6.414.929 ₫ total
includes taxes & fees
10 Dec - 11 Dec
Cornwall Inn and Lodge
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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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.

See all hotels in Sheffield
FTYTP1 The Upper Sheffield Covered Bridge, Sheffield, Massachusetts, USA

Top Sheffield Hotel Reviews

Prospect Berkshires

Prospect Berkshires

10/10 Excellent
"Wow, just wow! My high school friend and I met up at Prospect Berkshires for a girls weekend. We had an incredible time relaxing by using all the amenities. The staff are so helpful and profession. "
Kate 2-night trip
Posted 11 days ago
Prospect Berkshires
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

10/10 Excellent
"I visited Berkshire area for Thanksgiving and stayed at the brand new Holiday Inn Express. It was fantastic! The hotel is beautiful and pet friendly but also in a great location. The staff were amazing and professional. Over all 10/10 stay. Will definitely stay there again "
Kristina 2-night trip
Posted 11 days ago
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

More cheap stays in Sheffield

Quality Inn

Quality Inn

170 Housatonic Street Lee MA
The price is 2.386.552 ₫ per night from 28 Dec to 29 Dec
2.386.552 ₫
2.665.778 ₫ total
28 Dec - 29 Dec
includes taxes & fees
8.2/10 Very Good! (999 reviews)

Hotels in Sheffield with star rating

Frequently asked questions

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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