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Places to Stay in The Berkshires, Massachusetts

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Location

Massachusetts
The Berkshires

Age of Child

Beartown State Forest

The Berkshires, Massachusetts

Good for School-Age Kids

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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

Cranwell Resort, Spa and Golf Club

The Berkshires, Massachusetts

Good for Pre-Teens & Teens

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

Hotel / Motel

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

Eastover Resort and Conference Center

The Berkshires, Massachusetts

Remember when you were a kid and went to camp with your best friend? Eastover's where you get to go to camp with the whole family....

Hotel / Motel

New England Country Inn at Jiminy Peak

The Berkshires, Massachusetts

What you admire when you look out your window in the morning depends entirely on your age and disposition. Parents will relish the mountain view; kids will focus solely on the Alpine Super Slide. ...

Hotel / Motel

October Mountain State Forest

The Berkshires, Massachusetts

Proximity to Tanglewood (10 minutes away) is one of the benefits of this woodsy campground; fully-equipped facilities (including flush toilets) are some others. ...

Tent sites
Trailer sites
Fire pits
Bear country rules apply

Quality Inn Lee

The Berkshires, Massachusetts

The main draw at this cute motel on Laurel Lake is the water. Rooms on the lake side get to wake up to it, and boats (pontoon, pedal, or row) are available for guest rental out back. ...

Hotel / Motel

Red Lion Inn

The Berkshires, Massachusetts

Stay here for the lovely rooms and the vintage feel. The old stagecoach stop breathes history, from the lovely tea parlor to the old cage elevator (kids can actually ride it—just ask) to the grandfather clock that chimes on the hour. ...