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

Tonight
Sep 15 - Sep 16
Tomorrow
Sep 16 - Sep 17
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

Our top choices for Hancock family-friendly hotels

A wooden cabin with a porch and steps leading to a door, surrounded by snow.
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.
A hotel lobby with a reception desk, seating area with sofas and armchairs, a stone fireplace, and a television mounted on the wall.
A cozy living room with a stone fireplace, comfortable seating, and a welcoming sign.

1. Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
Hancock
  • Family-friendly mountain resort with pools and skiing thrills for all ages in Jiminy Peak.
₩191,983
₩214,445 total
includes taxes & fees
Sep 20 - Sep 21
Jiminy Peak Mountain Resort
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.
A reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.
A reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.
A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

2. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
Pittsfield
  • Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.
₩147,937
₩165,246 total
includes taxes & fees
Sep 17 - Sep 18
Best Western Plus Berkshire Hills Inn & Suites
A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.
A bathroom with a large mirror, a sink, and a towel rack.
A buffet area with a counter, food items, and a beverage station.

3. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
  • Family adventures await with a heated indoor pool, kid-friendly dining, and spacious suites in the heart of Pittsfield.
₩154,830
₩172,945 total
includes taxes & fees
Oct 13 - Oct 14
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.
A bathroom with a bathtub, a sink, and a mirror.
A hotel room with a TV, microwave, mini-fridge, desk, chair, mirror, and a coat rack.
A hotel room with a fitness center including a weight machine, an elliptical, and a treadmill.

4. FairBridge Inn Express

FairBridge Inn Express
Pittsfield
₩83,313
₩93,061 total
includes taxes & fees
Sep 21 - Sep 22
FairBridge Inn Express
View all properties

Choose what matters most at family-friendly hotels in Hancock

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Hancock Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Excellent location. Excellent adjacent restaurant "Door Prize". Will definitely stay again"
Dolores 3-night trip
Posted 1 hour ago
Hotel Downstreet, an Ascend Collection Hotel
The Red Lion Inn

The Red Lion Inn

8/10 Good
"Bedding and bed were lovely. excellent to have good lighting at sink as well as a magnified mirror! Often lacking in places we have stayed. AC had trouble cooling the room down until we turned it on full blast. too much ambient light from floodlight on property next door and from hall (I finally turned off hallway light which helped. ) Common areas and halls need some brightening up with fresh, lighter paint--seemed dingy. Was terribly frustrating trying to make the Nespresso machine work. We do not own one and there were NO INSTRUCTIONS. You should assume people do not know how to operate any appliances like that and should have a card with directions. We gave up and went to the Tavern where we had lovely coffee and breakfast. Also had a great dinner in Tavern after our arrival. The patch burrata salad was superb. As was our waitress."
Judith 1-night trip
Posted 2 hours ago
The Red Lion Inn
The Yankee Inn

The Yankee Inn

10/10 Excellent
"We were here for a good night’s rest on a cross country roadtrip. This place had very good Expedia reviews and I agree. Very clean, decent breakfast, plenty of hot water, a toilet that flushed properly. Did not use amenities. Sleep, shower, quiet time to read some, eat and on down the highway. Would gladly stay here again the next time thru the Berkshires."
Al 1-night trip
Posted 18 hours ago
The Yankee Inn
Hotel On North

Hotel On North

10/10 Excellent
"Great location, clean room!"
Gayle 1-night trip
Posted 1 day ago
Hotel On North

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, Colonial Theater, and Williamstown Theatre Festival. Make sure you have lots of time for activities like Bousquet Ski Area and The Clark Art Institute.

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