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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr
No exact matches found, but these alternatives could be just right

Recommended hotels in Sheffield

Exterior
Wilder House Berkshires

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 AED 565
AED 631 total
includes taxes & fees
18 Dec - 19 Dec
Wilder House Berkshires
Exterior detail
Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (41)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AED 724
AED 1,633 total
includes taxes & fees
14 Dec - 15 Dec
Cheerful 3-bedroom cottage with woodstove
Exterior
Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (9)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
The price is AED 1,506
AED 2,626 total
includes taxes & fees
14 Dec - 15 Dec
Guesthouse Cabin vacation rentals in Berkshire County
Exterior
Element Lenox Berkshires

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 AED 481
AED 537 total
includes taxes & fees
17 Dec - 18 Dec
Element Lenox Berkshires
Exterior
The Yankee, Trademark Collection by Wyndham

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 there!! Very friendly staff"
United States
Ann
The price is AED 275
AED 307 total
includes taxes & fees
24 Dec - 25 Dec
The Yankee, Trademark Collection by Wyndham
Garden
Shaker Mill Inn

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 AED 396
AED 435 total
includes taxes & fees
14 Dec - 15 Dec
Shaker Mill Inn
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828)
"Staff was very friendly and helpful."
United States
Pamela
The price is AED 290
AED 324 total
includes taxes & fees
11 Dec - 12 Dec
Howard Johnson by Wyndham Lenox
Exterior
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

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 AED 398
AED 444 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Exterior
Quality Inn Great Barrington

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1001)
"Clean room, nice location "
United States
Devron
The price is AED 278
AED 310 total
includes taxes & fees
23 Dec - 24 Dec
Quality Inn Great Barrington
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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, (1000)
"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 AED 372
AED 415 total
includes taxes & fees
24 Dec - 25 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
Monument Mountain Motel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (804)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel
Exterior
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (786)
"This place is so peaceful and the staff is always helpful "
United States
Leona
The price is AED 362
AED 487 total
includes taxes & fees
8 Jan - 9 January 2026
Berkshire Mountain Lodge
Exterior
Hampton Inn & Suites Berkshires-Lenox

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 AED 379
AED 423 total
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn & Suites Berkshires-Lenox
Front of property
The Little Lion

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (547)
"The check-in was easy and the room was ready and clean. It was nice having our dogs with us. "
United States
Maria
The price is AED 404
AED 451 total
includes taxes & fees
1 Jan - 2 January 2026
The Little Lion
Exterior
Hilton Garden Inn Lenox Pittsfield

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 AED 379
AED 423 total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Lenox Pittsfield
Aerial view
Locust Tree Bed and Breakfast LLC

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 AED 386
AED 443 total
includes taxes & fees
17 Dec - 18 Dec
Locust Tree Bed and Breakfast LLC
Dinner served, American cuisine
the Alander

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 AED 514
AED 576 total
includes taxes & fees
11 Dec - 12 Dec
the Alander
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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, (707)
"Great hospitality "
United States
regina maria
The price is AED 393
AED 439 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1002)
"Clean room and good breakfast "
United States
Kelly
The price is AED 332
AED 371 total
includes taxes & fees
28 Dec - 29 Dec
Quality Inn Lee - Lenox South
Exterior
The Red Lion Inn

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 AED 549
AED 777 total
includes taxes & fees
6 Jan - 7 January 2026
The Red Lion Inn
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 Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Really quiet, peaceful stay and beautiful spot for the money. Front desk staff so nice. No elevator to second floor so keep in mind if have accessibility issues/wheelchair user. Great view and gluten free menu options. Would stay again if in area. Was just passing through on way to medical appointment. "
Meaghan 1-night trip
Posted 1 day ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel