Best Resorts in Sheffield

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Nov 14 - Nov 16
In two weeks
Nov 21 - Nov 23
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Dec 5 - Dec 7
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Jan 2 - Jan 4

Resorts in Sheffield

No exact matches found, but these alternatives could be just right

Recommended hotels in Sheffield

Wilder House Berkshires Room 3 | 1 bedroom, premium bedding, individually decorated
Wilder House Berkshires

Wilder House Berkshires

2.0 star property
Sheffield
9.8 out of 10, Exceptional, (37)
"Highly recommend this beautiful bed & breakfast! The room was wonderful and overlooked the property, the breakfast was delicious, and the hospitality was amazing. I had a fantastic stay, and will definitely stay at The Wilder House again when I'm in the area."
United States
Marina
$155 nightly
The price is $174
Nov 17 - Nov 18
Total with taxes and fees
Wilder House Berkshires
Dining
Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County

Sheffield
10.0 out of 10, Exceptional, (9)
"Two very comfortable nights. Cabin is well appointed. Great kitchen and outdoor space. Tremendous views, amazing star gazing. Very private. "
United States
Robert B.
$617 nightly
The price is $689
Nov 10 - Nov 11
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

Sheffield
10.0 out of 10, Exceptional, (40)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
$404 nightly
The price is $451
Nov 9 - Nov 10
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
Garden
Shaker Mill Inn

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (433)
"Nice place, easy check in"
United States
Robert
$102 nightly
The price is $112
Nov 12 - Nov 13
Total with taxes and fees
Shaker Mill Inn
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (782)
"This was an older property, but room was nice and bathroom was updated. "
United States
Martha
$67 nightly
The price is $74
Nov 9 - Nov 10
Total with taxes and fees
Monument Mountain Motel
Lobby
Quality Inn

Quality Inn

2.5 star property
Lee
8.4 out of 10, Very Good, (1000)
"Fine lodging for short term business stay"
United States
Lawrence
$87 nightly
The price is $98
Dec 1 - Dec 2
Total with taxes and fees
Quality Inn
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, (1003)
"Good for one night stay"
United States
Marla
$110 nightly
The price is $122
Nov 30 - Dec 1
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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, (690)
"Solid location, great room, good breakfast. Fair Price. Been 3 different times and look forward to returning again "
United States
Jamie
$107 nightly
The price is $120
Nov 30 - Dec 1
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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 place. Friendly staff and very well located. Great breakfast options. "
United States
Abiezer
$101 nightly
The price is $113
Nov 18 - Nov 19
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
7.6 out of 10, Good, (818)
"Staff was very friendly and helpful."
United States
Pamela
$79 nightly
The price is $88
Nov 9 - Nov 10
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (748)
"Everything was so perfect for a weekend to just get away and decompress, the staff were great, the room was awesome. "
United States
Jeff
$113 nightly
The price is $126
Nov 9 - Nov 10
Total with taxes and fees
Berkshire Mountain Lodge
In-room safe, desk, free cribs/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, (556)
"I loved the stay people were nice loved the pool and internet was great "
United States
Jennifer
$75 nightly
The price is $84
Nov 8 - Nov 9
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires
Exterior
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

2.0 star property
West Stockbridge
6.8 out of 10, (1001)
"good average place to stay."
United States
Terry
$58 nightly
The price is $64
Nov 12 - Nov 13
Total with taxes and fees
Pleasant Valley Motel West Stockbridge
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, (410)
"Peaceful area and great staff; Thank you for the service and experience "
United States
Andre
$105 nightly
The price is $121
Nov 9 - Nov 10
Total with taxes and fees
Locust Tree Bed and Breakfast LLC
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.6 out of 10, Exceptional, (9)
"Very friendly with dog. No complaints with accommodations "
United States
Lilian
$135 nightly
The price is $151
Nov 16 - Nov 17
Total with taxes and fees
Element Lenox Berkshires
Lobby
Quality Inn

Quality Inn

2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1002)
"Nice and clean would stay again."
United States
Stephen
$84 nightly
The price is $94
Nov 23 - Nov 24
Total with taxes and fees
Quality Inn
Seasonal outdoor pool
Sunset Inn

Sunset Inn

2.0 star property
Lee
7.6 out of 10, Good, (409)
"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
$81 nightly
The price is $90
Dec 2 - Dec 3
Total with taxes and fees
Sunset Inn
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (56)
"Bright new hotel with very friendly and helpful staff. "
United States
Mary
$118 nightly
The price is $132
Dec 2 - Dec 3
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - 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, (656)
"Lovely hotel, room was great along with the staff and the grounds where beautiful. Thank you."
United States
Vicki
$111 nightly
The price is $124
Nov 16 - Nov 17
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
Exterior
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"The staff is very friendly and helpful "
United States
karin
$111 nightly
The price is $124
Nov 16 - Nov 17
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
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

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Solid location, great room, good breakfast. Fair Price. Been 3 different times and look forward to returning again "
Jamie 2-night trip
Posted 1 day ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Find out more about Sheffield

Sheffield Resorts information

Number of reviews
11,638
Accommodation
5 Resorts
Lowest Price
$64
Highest Price
$689

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, Magnolia Bluffs Casino, and Mount Everett State Reservation are a few of the interesting sights to visit. Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary 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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