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Check availability on Sheffield Family Hotels

Our top choices for Sheffield family-friendly hotels

Lake

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, (1,004 reviews)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is NT$3,087
NT$3,448 total
includes taxes & fees
Mar 2 - Mar 3
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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, (567 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is NT$2,369
NT$2,646 total
includes taxes & fees
Feb 11 - Feb 12
Travelodge by Wyndham Great Barrington Berkshires
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, (833 reviews)
"Great overnights stay, wish I was here longer "
United States
Thomas
The price is NT$3,553
NT$4,586 total
includes taxes & fees
Mar 1 - Mar 2
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (18 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is NT$4,403
NT$4,918 total
includes taxes & fees
Feb 22 - Feb 23
Element Lenox Berkshires
Property amenity

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (767 reviews)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is NT$4,769
NT$5,327 total
includes taxes & fees
Feb 25 - Feb 26
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
In-room dining

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (658 reviews)
"The room was clean and the service adequate"
United States
David
The price is NT$2,013
NT$2,249 total
includes taxes & fees
Feb 24 - Feb 25
Econo Lodge Lee - Great Barrington
Indoor pool

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, (82 reviews)
"it was a lovely hotel, hot tub was perfect after the day of skiing, everything very clean and new and lovely breakfast. All staff were very nice."
United States
Laura Pearson
The price is NT$4,170
NT$4,658 total
includes taxes & fees
Mar 1 - Mar 2
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Exterior

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.0 out of 10, Very Good, (13 reviews)
"Antonia was wonderful and made our stay special. She was kind and warm and when we were initially unhappy with our room immediately rectified the situation and in the end our stay was perfect! It’s a charming hotel, clean and centrally located, walking distance to all the local shops in town."
United States
Jamie
The price is NT$5,091
NT$5,759 total
includes taxes & fees
Feb 11 - Feb 12
The Millerton Inn
Deluxe Room, 1 King Bed, Ensuite (2nd Floor) | Premium bedding, individually decorated, individually furnished, desk

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (109 reviews)
"Great experience, looking forward to staying again."
United States
Greg
The price is NT$4,421
NT$4,952 total
includes taxes & fees
Feb 11 - Feb 12
Changing Times Boutique Country Lodging
Free WiFi, bed sheets

Hitching Post Country Motel

Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.6 out of 10, (81 reviews)
"Basic accommodation that was clean and easy."
United States
Elizabeth
The price is NT$4,106
NT$4,721 total
includes taxes & fees
Feb 11 - Feb 12
Hitching Post Country Motel
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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Choose what matters most at family-friendly hotels in Sheffield

Breakfast included
Pool

Top Sheffield Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"The staff is very helpful, and always willing to assist with any inquiries. The room was definitely clean and well-stocked throughout our entire stay."
Robin 1-night trip
Posted 5 days ago
The Yankee, Trademark Collection by Wyndham

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 Holley-Williams House Museum and Infinity Music Hall and Bistro.

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