Find hotels in Sheffield, MA from 2.227.701 ₫

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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 4.270.806 ₫
4.770.490 ₫ total
includes taxes & fees
9 Dec - 10 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, (1000)
"Great stay!"
United States
Ann
The price is 2.352.898 ₫
2.628.187 ₫ total
includes taxes & fees
14 Dec - 15 Dec
The Yankee, Trademark Collection by Wyndham
Garden
Shaker Mill Inn

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (436)
"Nice place, easy check in"
United States
Robert
The price is 2.873.567 ₫
3.152.304 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Shaker Mill 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, (703)
"We stay here every year and it never disappoints "
United States
Elizabeth
The price is 2.820.841 ₫
3.150.880 ₫ total
includes taxes & fees
12 Dec - 13 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is 3.453.553 ₫
3.857.619 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Element Lenox 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, (1002)
"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 2.667.936 ₫
2.980.085 ₫ total
includes taxes & fees
15 Dec - 16 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lobby
Quality Inn

Quality Inn

2.5 star property
Great Barrington
8.4 out of 10, Very good, (1000)
"Clean room, nice location "
United States
Devron
The price is 1.994.361 ₫
2.227.701 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Quality Inn
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (803)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel
Exterior
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is 2.720.662 ₫
3.038.980 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Hampton Inn & Suites Berkshires-Lenox
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 4.059.902 ₫
5.712.862 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
The Red Lion Inn
Exterior
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

2.0 star property
West Stockbridge
6.8 out of 10, (1002)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is 1.399.875 ₫
1.535.663 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Pleasant Valley Motel West Stockbridge
Seasonal outdoor pool
Sunset Inn

Sunset Inn

2.0 star property
Lee
7.6 out of 10, Good, (410)
"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "
United States
Kimberly
The price is 2.372.670 ₫
2.650.272 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Sunset Inn
Terrace/patio
Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

3.0 star property
East Canaan
9.0 out of 10, Wonderful, (413)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is 2.768.115 ₫
3.183.332 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Locust Tree Bed and Breakfast LLC
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 2.554.575 ₫
2.853.460 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
In-room safe, desk, free cots/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
Great Barrington
7.6 out of 10, Good, (562)
"The staff were very friendly and accommodating "
United States
Tom
The price is 1.977.225 ₫
2.208.692 ₫ total
includes taxes & fees
9 Dec - 10 Dec
Travelodge by Wyndham Great Barrington Berkshires
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (779)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge
Lobby
Quality Inn

Quality Inn

2.5 star property
Lee
8.4 out of 10, Very good, (1000)
"Clean room and good breakfast "
United States
Kelly
The price is 2.386.642 ₫
2.665.880 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Quality Inn
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
7.6 out of 10, Good, (827)
"Staff was very friendly and helpful."
United States
Pamela
The price is 2.082.677 ₫
2.326.271 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Howard Johnson by Wyndham Lenox
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, (795)
"Place was great!"
United States
Benjamin
The price is 3.361.283 ₫
4.269.950 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (657)
"Clean and convenient to Mt. Greylock. Kind staff. "
United States
Kristen
The price is 2.720.662 ₫
3.038.980 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Hilton Garden Inn Lenox Pittsfield
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

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 8 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 8 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 2.386.642 ₫ per night from 28 Dec to 29 Dec
2.386.642 ₫
2.665.880 ₫ 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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