A road lined with autumn-colored trees, a green house, and a mountain in the background.

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Check availability on Hancock Family Hotels

This weekend
Jul 31 - Aug 2
Next weekend
Aug 7 - Aug 9

Our top choices for Hancock family-friendly hotels

Daily to-go breakfast for a fee

1. Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very Good, (1,000 reviews)
  • cleanliness
    Family-friendly mountain resort with pools and skiing thrills for all ages in Jiminy Peak.
The price is ₩228,855
₩255,631 total
includes taxes & fees
Aug 30 - Aug 31
Jiminy Peak Mountain Resort
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, desk, laptop workspace, blackout drapes

2. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.
The price is ₩164,056
₩183,251 total
includes taxes & fees
Aug 31 - Sep 1
Best Western Plus Berkshire Hills Inn & Suites
Desk, iron/ironing board, WiFi (free), bed sheets

3. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (861 reviews)
The price is ₩89,383
₩99,841 total
includes taxes & fees
Aug 16 - Aug 17
FairBridge Inn Express
Restaurant

4. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
7.8 out of 10, Good, (1,005 reviews)
  • cleanliness
    Family adventures await with a heated indoor pool, kid-friendly dining, and spacious suites in the heart of Pittsfield.
The price is ₩171,281
₩191,321 total
includes taxes & fees
Aug 31 - Sep 1
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior

5. Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (935 reviews)
The price is ₩136,018
₩159,623 total
includes taxes & fees
Aug 5 - Aug 6
Cozy Corner Motel
Exterior

6. Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (628 reviews)
The price is ₩185,675
₩207,395 total
includes taxes & fees
Aug 9 - Aug 10
Maple Terrace Motel
Indoor pool

7. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (148 reviews)
  • cleanliness
    Splash into family fun with indoor pool and hot tub—just minutes from Bousquet Ski Area and Tanglewood Music Center.
The price is ₩205,826
₩229,907 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
BBQ/picnic area

8. Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (335 reviews)
The price is ₩171,281
₩191,321 total
includes taxes & fees
Aug 6 - Aug 7
Williamstown Motel
Lobby

9. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (31 reviews)
The price is ₩316,800
₩353,866 total
includes taxes & fees
Aug 19 - Aug 20
Element by Marriott Lenox Berkshires
Miscellaneous

10. 1896 House Country Inn & Motels

1896 House Country Inn & Motels
2.5 star property
Williamstown
6.6 out of 10, (453 reviews)
The price is ₩152,930
₩170,823 total
includes taxes & fees
Aug 6 - Aug 7
1896 House Country Inn & Motels
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 Hancock

Breakfast included
Pool

Top Hancock Hotel Reviews

The Yankee Inn

The Yankee Inn

8/10 Good
"We made the most out of getting 3 days of rain on our 4 day trip. Not too much for kids to do. Expect alot of mosquitoes if you're in the back of the property by the pond. Tow"
AmandA 4-night trip
Posted 7 hours ago
The Yankee Inn

Frequently asked questions

What's Hancock like for family-friendly vacations?
If you've been thinking about a vacation with your kids, Hancock is a good choice. The entertainment, museums, and snowboarding are just a few things that make this an attractive vacation spot for families. Take to the air and fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is the closest airport, or Hudson, NY (HCC-Columbia County), which is located 28.1 mi (45.2 km) from the city center.
What's the best place to stay for a family trip to Hancock?
Jiminy Peak Mountain Resort is a hotel with an outdoor pool and a restaurant, and it's a top choice on Expedia for families.
When's the best time to book a family-friendly vacation in Hancock?
The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 26°F. The snowiest months in Hancock 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 Hancock?
While you are visiting Hancock, you might want to round up the kiddos and make time to see interesting attractions such as Jiminy Peak Mountain Resort, Barrington Stage Company, and Colonial Theater. Make sure you have lots of time for activities like Williamstown Theatre Festival and Bousquet Ski Area.