Find hotels in Sheffield, MA from 1.840.569 ₫

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4 Dec - 5 Dec
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5 Dec - 7 Dec
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Top 10 Sheffield hotels and places to stay

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 4.272.426 ₫
4.772.299 ₫ total
includes taxes & fees
9 Dec - 10 Dec
Wilder House Berkshires
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, (1001)
"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 2.668.948 ₫
2.981.215 ₫ total
includes taxes & fees
18 Dec - 19 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Great stay!"
United States
Ann
The price is 1.647.778 ₫
1.840.569 ₫ total
includes taxes & fees
14 Dec - 15 Dec
The Yankee, Trademark Collection by Wyndham
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (806)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is 2.891.721 ₫
3.230.052 ₫ total
includes taxes & fees
8 Dec - 9 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, (794)
"Place was great!"
United States
Benjamin
The price is 2.808.725 ₫
3.598.875 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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 4.235.351 ₫
4.872.814 ₫ total
includes taxes & fees
5 Dec - 6 Dec
The Cornell Inn, Lenox & The Berkshires
Outdoor pool, pool loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1000)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is 3.402.375 ₫
4.978.809 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
The Red Lion Inn
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (777)
"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, (64)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is 2.405.400 ₫
2.686.832 ₫ 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, (185)
"Very nice clean place in a beautiful area. "
United States
Wayne
The price is 3.692.220 ₫
4.135.287 ₫ total
includes taxes & fees
8 Dec - 9 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
7.6 out of 10, Good, (117)
"Yes everything was perfect, just had a little trouble getting the WIFI for the TV set up! "
United States
Zenovia
The Brooks Motel
Library
Blackberry River Inn

Blackberry River Inn

3.0 star property
Norfolk
9.4 out of 10, Exceptional, (162)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is 4.334.403 ₫
4.984.564 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Blackberry River Inn
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
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, (702)
"Everything was wonderful....super clean rooms, check-in was fast and smooth, staff was on top of everything. We definitely will be back at Holiday Inn. "
United States
Tabitha
The price is 2.821.911 ₫
3.152.074 ₫ total
includes taxes & fees
12 Dec - 13 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 star property
Lenox
9.2 out of 10, Wonderful, (588)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is 3.560.355 ₫
3.976.917 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Courtyard by Marriott Lenox Berkshires
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 6.856.980 ₫
8.543.006 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Prospect 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, (757)
"Clean room, very courteous staff "
United States
Thomas
The price is 3.982.323 ₫
4.448.255 ₫ total
includes taxes & fees
8 Dec - 9 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, (300)
"Great stay"
United Kingdom
Katherine
The price is 6.527.317 ₫
7.384.027 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Inn at Pine Plains
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, (154)
"This inn was very quaint and welcoming. It was a nice inn for the value. "
United States
Jacqueline
The price is 5.580.527 ₫
6.417.606 ₫ total
includes taxes & fees
5 Dec - 6 Dec
Cornwall Inn and Lodge
Porch
Interlaken Inn & Resort

Interlaken Inn & Resort

3.5 star property
Lakeville
8.2 out of 10, Very good, (270)
"The staff is courteous and accommodating especially the restaurant staff."
United States
Christian
The price is 5.910.189 ₫
6.796.717 ₫ total
includes taxes & fees
6 Dec - 7 Dec
Interlaken Inn & Resort
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

Ashley House

You can learn about the history of Sheffield when you stop by Ashley House. Discover the area's breweries or seek out the hiking trails.
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Thom Reed UFO Monument Park

Explore the great outdoors at Thom Reed UFO Monument Park, a lovely green space in Sheffield. Make some time to visit the casinos while you're in the area.
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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.

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

Top Sheffield Hotel Reviews

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 6 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 2.389.658 ₫ per night from 28 Dec to 29 Dec
2.389.658 ₫
2.669.247 ₫ total
28 Dec - 29 Dec
includes taxes & fees
8.2/10 Very Good! (1,002 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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