This 3-bedroom, 2.5-bath home sits on a full acre in a quiet neighborhood, with plenty of space outside for kids to run and play.

Berkshires Fall Escape with Views & Cozy Fireplace

3 bedrooms·2½ baths
5(28 reviews)
$271 – $595/ night(excl. fees & taxes)
Ruins of Ashintully, 1/4 mile walk up hill from the cottage

Ashintully Cottage

4 bedrooms·3 baths
5(45 reviews)
$450/ night(excl. fees & taxes)
Berkshires Cottage | Trails & Water Nearby

Berkshires Cottage | Trails & Water Nearby

2 bedrooms·1 bath
$133 – $309/ night(excl. fees & taxes)
7 person Artesian Grand Cayman hot tub with all the bells and whistles.

The Meadows House @ Otis Ridge w/ 7-person hot tub

3 bedrooms·2 baths
4.84(204 reviews)
$225 – $295/ night(excl. fees & taxes)
Hygge House on Richmond Pond

Hygge House on Richmond Pond

3 bedrooms·2 baths
4.95(62 reviews)
$450 – $644/ night(excl. fees & taxes)
Berkshire Farm Sanctuary-A home of love & kindness image 1

Berkshire Farm Sanctuary-A home of love & kindness

3 bedrooms·2 baths
5(42 reviews)
$500/ night(excl. fees & taxes)
After a day on the slopes, head straight to John Harvard’s. Just upstairs, no driving, no cooking, just comfort, delicious food, and crackling warmth.

Ski-in/Ski-out 1BR Condo at Jiminy Peak

1 bedroom·1 bath
$100/ night(excl. fees & taxes)