Find Family Hotels in Sheffield, MA

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Check availability on Sheffield Family Hotels

Tonight
Nov 23 - Nov 24
Tomorrow
Nov 24 - Nov 25
Next weekend
Nov 28 - Nov 30
In two weeks
Dec 5 - Dec 7

Top Sheffield Family Hotels

Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1007)
"Great stay!"
United States
Ann
The price is NT$2,019
NT$2,256 total
includes taxes & fees
Dec 7 - Dec 8
The Yankee, Trademark Collection by Wyndham
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, (560)
"The staff were very friendly and accommodating "
United States
Tom
The price is NT$2,357
NT$2,633 total
includes taxes & fees
Nov 25 - Nov 26
Travelodge by Wyndham Great Barrington Berkshires
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 NT$4,116
NT$4,598 total
includes taxes & fees
Dec 11 - Dec 12
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 NT$3,339
NT$3,729 total
includes taxes & fees
Dec 14 - Dec 15
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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, (60)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is NT$3,117
NT$3,482 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 star property
Lenox
9.2 out of 10, Wonderful, (587)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is NT$3,991
NT$4,458 total
includes taxes & fees
Nov 30 - Dec 1
Courtyard by Marriott Lenox Berkshires
Property grounds
Wagon Wheel Inn

Wagon Wheel Inn

2.0 star property
Lenox
7.0 out of 10, Good, (641)
"Beautiful area. Close to Mt. Greylock, Octobrr Mountain and Pleasant Valley Audubon."
United States
Benjamin
The price is NT$2,168
NT$2,422 total
includes taxes & fees
Nov 24 - Nov 25
Wagon Wheel Inn
Arcade
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, (789)
"Place was great!"
United States
Benjamin
The price is NT$3,347
NT$4,177 total
includes taxes & fees
Nov 30 - Dec 1
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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

Monument Mountain Motel

Monument Mountain Motel

10/10 Excellent
"This hotel was perfect for our one night stay. The room was very clean, bed was comfortable and the shower had good water pressure. The owners were very friendly. They had kuerig coffee available in the lobby, which was perfect to grab a cup of coffee to go."
Jeanne 1-night trip
Posted 2 days ago
Monument Mountain Motel

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Frequently asked questions

What's Sheffield like for family-friendly vacations?
If you've been thinking about a trip with your kids, the historic destination of Sheffield is a good choice. The local tours here makes this a great vacation spot for families. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 22 mi (35.4 km) from the city center.
When's the best time to book a family-friendly vacation 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 there to see and do with your family in Sheffield?
While you are visiting Sheffield, you might want to round up the kiddos and make time to see interesting attractions such as Ski Butternut, Mahaiwe Performing Arts Center, and Catamount Ski Area. Make sure you have lots of time for activities like Harney and Sons Tea Tasting Room and Holley-Williams House Museum.