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Places to Stay in The Berkshires, Massachusetts

See The Berkshires, Massachusetts family vacation

Find Places to Stay by:

Location

  • Massachusetts
  • The Berkshires

Age of Child

  • Toddlers & Pre-K

Cranwell Resort, Spa and Golf Club

The Berkshires, Massachusetts

Good for Toddlers & Pre-K

**** see all ratings

The only local "castle" that welcomes wee ones, Cranwell is a bona fide vacation destination in itself, with sprawling grounds and pool. ...

  • Hotel / Motel

Beartown State Forest

The Berkshires, Massachusetts

Good for Toddlers & Pre-K

*** see all ratings

Campgrounds near Benedict Pond enjoy proximity to one of the loveliest swimming holes in the area, plus a place to put in your non-motorized boat.. ...

    • Tent sites
    • Day use
    • Bear country rules apply
    • Toilets

Jiminy Peak Mountain Resort

The Berkshires, Massachusetts

Good for Toddlers & Pre-K

** see all ratings

Jiminy's newfangled spring/summer Mountain Coaster raises the bar on the alpine slide genre, laying elevated tracks down the length of a ski slope and sending rider-steered cars careening down drops, around corners, and through its top-speed course....

  • Resort

  • Bicycling

  • Hiking

  • Skiing

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