Best Resorts in Sheffield

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Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11
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Jan 23 - Jan 25
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Feb 20 - Feb 22
No exact matches found, but these alternatives could be just right

Recommended hotels in Sheffield

Interior detail
Wilder House Berkshires

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (41)
"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
$151 nightly
The price is $169
Dec 30 - Dec 31
Total with taxes and fees
Wilder House Berkshires
Interior
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.
$604 nightly
The price is $675
Jan 4 - Jan 5, 2026
Total with taxes and fees
Guesthouse Cabin vacation rentals in Berkshire County
Property grounds
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.
$450 nightly
The price is $503
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
Lobby
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (14)
"Rooms were very clean and spacious."
United States
Morgan
$135 nightly
The price is $151
Jan 4 - Jan 5, 2026
Total with taxes and fees
Element Lenox Berkshires
Desk, laptop workspace, blackout drapes, iron/ironing board
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1001)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
$52 nightly
The price is $57
Jan 1 - Jan 2, 2026
Total with taxes and fees
Pleasant Valley Motel West Stockbridge
Lobby
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, (1003)
"The staff is always so helpful & nice, and the rooms are always clean and comfortable. This is my favorite place to stay in Lee!"
United States
Cooper
$83 nightly
The price is $92
Jan 11 - Jan 12, 2026
Total with taxes and fees
Quality Inn Lee - Lenox South
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, (1006)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
$76 nightly
The price is $85
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham
Miscellaneous
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, (1007)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
$100 nightly
The price is $112
Jan 12 - Jan 13, 2026
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (438)
"Nice place, easy check in"
United States
Robert
$106 nightly
The price is $117
Jan 5 - Jan 6, 2026
Total with taxes and fees
Shaker Mill Inn
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (809)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
$67 nightly
The price is $74
Dec 24 - Dec 25
Total with taxes and fees
Monument Mountain Motel
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, (710)
"Great hospitality "
United States
regina maria
$107 nightly
The price is $120
Jan 4 - Jan 5, 2026
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Lobby lounge
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
$104 nightly
The price is $116
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
In-room safe, desk, laptop workspace, iron/ironing board
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
$79 nightly
The price is $88
Dec 24 - Dec 25
Total with taxes and fees
Howard Johnson by Wyndham Lenox
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)
"Old time charm and hot tub under the stars"
United States
Lori
$178 nightly
The price is $199
Jan 14 - Jan 15, 2026
Total with taxes and fees
The Red Lion Inn
In-room safe, desk, free cribs/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

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
$75 nightly
The price is $84
Dec 24 - Dec 25
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires
Lobby
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)
"My go to place for my ski weekends"
United States
Ryan
$76 nightly
The price is $85
Jan 5 - Jan 6, 2026
Total with taxes and fees
Quality Inn Great Barrington
Check-in/check-out kiosk
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (794)
"Spacious room and loved pool and hot tub!"
United States
Deanna
$108 nightly
The price is $120
Jan 21 - Jan 22, 2026
Total with taxes and fees
Berkshire Mountain Lodge
Exterior
Prospect Berkshires

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
$196 nightly
The price is $219
Jan 4 - Jan 5, 2026
Total with taxes and fees
Prospect Berkshires
Exterior
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
$105 nightly
The price is $121
Dec 24 - Dec 25
Total with taxes and fees
Locust Tree Bed and Breakfast LLC
Terrace/patio
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, (659)
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
$128 nightly
The price is $143
Jan 2 - Jan 3, 2026
Total with taxes and fees
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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Top Sheffield Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Spacious room and loved pool and hot tub!"
Deanna 5-night trip
Posted 4 days ago
Berkshire Mountain Lodge

Find out more about Sheffield

Sheffield Resorts information

Number of reviews
12,275
Accommodation
4 Resorts
Lowest Price
$57
Highest Price
$675

Frequently asked questions

What can I expect from a resort vacation in Sheffield?
Longing for a relaxing getaway? Indulge in all the comforts of a resort, where you can find everything you need for your stay from convenient food and drink options to activities and shopping. Browse the resort options in the area and discover the right one for you, whether you envision yourself sipping drinks by a sprawling pool or hitting the golf course for an afternoon game.
What's a top resort in Sheffield?
Our highest-rated resort near Sheffield: Holiday Inn Club Vacations Oak 'n Spruce Resort - Ski resort. 12.2 mi (19.6 km) from Sheffield. Has a sauna, a fitness center, and a terrace.
What can I do in Sheffield?
Housatonic River, Thom Reed UFO Monument Park, and Magnolia Bluffs Casino are a few of the interesting sights to visit. Three Mile Pond Wildlife Management Area and Ashley House are a few additional attractions in the area that you might like.
What's the weather like in Sheffield?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Sheffield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's the best way to get to and around Sheffield?
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 22 mi (35.4 km) from the city center. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 22.3 mi (35.9 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.

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