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Compare 6 Resorts in Sheffield with updated reviews, rates, and availability.

Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
Pool

Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!

10.0 out of 10, Exceptional, (1)
"We loved everything about this place! It was quiet, centrally located, and everyone was friendly and helpful. We will stay here again for sure!"
Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
Canyon Ranch Lenox
Room

Canyon Ranch Lenox

3.0 star property
Canyon Ranch Lenox
Mountain Lodge Apt!
Interior

Mountain Lodge Apt!

Mountain Lodge Apt!
Holiday Inn Club Vacations Oak 'n Spruce Resort
Pool

Holiday Inn Club Vacations Oak 'n Spruce Resort

2.0 star property
Holiday Inn Club Vacations Oak 'n Spruce Resort
Terrific 2-bedroom resort in Lee with WiFi, fitness room, AC
Living area

Terrific 2-bedroom resort in Lee with WiFi, fitness room, AC

2.0 star property
Terrific 2-bedroom resort in Lee with WiFi, fitness room, AC
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires
Miscellaneous

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires
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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Other property types in Sheffield

Antique Farmhouse Totally Restored
Sunrise lights up the front of the house. Moon sets over the mountain.

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (83)
"I'd describe the house as elegantly eclectic. The owner is clearly a collector of interesting items which they arrange in a way that enhance (rather than potentially clutter) the interior. The kitchen and living spaces are open and easy to mingle around. The four bedrooms and three bathrooms easily and comfortably accommodated two couples and two singles. Our stay could not have been better! "
Antique Farmhouse Totally Restored
Cheerful 3-bedroom cottage with woodstove
great kitchen for cooking in

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (35)
"We stayed at this home about the same time last year and we were so happy with everything about it, we jumped at the opportunity to stay there again. The house has absolutely everything you'd need and is close to Canaan, CT and Great Barrington, MA and everything the Bershires have to offer. Sabrina is a great host and responded within minutes to any questions I had. We HIGHLY recommend this home."
The price is AED 871
AED 1,863 total
includes taxes & fees
6 Jan - 7 Jan
Cheerful 3-bedroom cottage with woodstove
Peace and quiet on the lake
Exterior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (201)
"My family and I really enjoyed our stay at the lake. My kids enjoyed playing outside in the snow. We had such a quality family time playing board games, watching movies and drinking hot cocoa. Justin was such a great host and really helpful when needed. We’re definitely coming back!"
Peace and quiet on the lake
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.

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. Enjoy the sauna, fitness center, and terrace.
What can I do in Sheffield?
Housatonic River, Three Mile Pond Wildlife Management Area, and Bartholomews Cobble are a few of the interesting sights to visit. Mount Everett State Reservation and Thom Reed UFO Monument Park 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.