Find Family Hotels in Sheffield, MA

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Check availability on Sheffield Family Hotels

Tonight
Mar 31 - Apr 1
Tomorrow
Apr 1 - Apr 2
This weekend
Apr 3 - Apr 5
Next weekend
Apr 10 - Apr 12

Our top choices for Sheffield family-friendly hotels

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, (113 reviews)
"Great experience, looking forward to staying again."
United States
Greg
The price is NT$4,793
NT$5,368 total
includes taxes & fees
Apr 1 - Apr 2
Changing Times Boutique Country Lodging
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, (574 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is NT$2,396
NT$2,677 total
includes taxes & fees
Apr 3 - Apr 4
Travelodge by Wyndham Great Barrington Berkshires
Lake

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,002 reviews)
"Room was spotless, staff was very kind!"
United States
Ilia
The price is NT$3,123
NT$3,489 total
includes taxes & fees
Apr 22 - Apr 23
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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, (87 reviews)
"New hotel clean and nice. Heated pool and hot tub a bonus. Timely breakfast for early departures- great on demand coffee. Added bonus they have a car charger."
United States
Charline
The price is NT$3,770
NT$4,212 total
includes taxes & fees
Apr 6 - Apr 7
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Free WiFi, bed sheets

Hitching Post Country Motel

Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.6 out of 10, (83 reviews)
"Checkin was easy, room was clean and comfortable "
United States
Greg
The price is NT$4,154
NT$4,777 total
includes taxes & fees
Apr 1 - Apr 2
Hitching Post Country Motel
Exterior

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.4 out of 10, Very Good, (18 reviews)
"Perfect "
United States
Zhigang
The price is NT$8,023
NT$9,076 total
includes taxes & fees
Apr 2 - Apr 3
The Millerton Inn
Property amenity

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (776 reviews)
"Staff was lovely, everything was easy, clean and comfortable"
United States
Helena
The price is NT$4,866
NT$5,435 total
includes taxes & fees
Apr 6 - Apr 7
Fairfield Inn & Suites by Marriott Great Barrington Lenox/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.
View all properties

Choose what matters most at family-friendly hotels in Sheffield

Breakfast included
Pool

Top Sheffield Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"The Quality Inn in Great Barrington is a good value play. The room we had was clean; the staff was friendly and knowledgeable; and the heating was welcomed on this March day. Breakfast was a weak point, but the coffee was good and available throughout the day. And yes, I would stay there again. "
Leslie 1-night trip
Posted 15 hours ago
Quality Inn Great Barrington

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, Catamount Ski Area, and Harney and Sons Tea Tasting Room. Make sure you have lots of time for activities like Holley-Williams House Museum and Infinity Music Hall and Bistro.

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