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
$155 – $341/ 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)
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 – $750/ night(excl. fees & taxes)
Hygge House on Richmond Pond

Hygge House on Richmond Pond

3 bedrooms·2 baths
4.95(62 reviews)
$644/ 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)
Jiminy Peak Slopeside Getaway • Ski & Adventure

Jiminy Peak Slopeside Getaway • Ski & Adventure

2 bedrooms·2 baths
$155 – $445/ night(excl. fees & taxes)
View of the Property

Plainfield House

3 bedrooms·2 baths
4.85(242 reviews)
$223 – $475/ night(excl. fees & taxes)