View of the Property
Dining room
Dining room
Kitchen
Kitchen

Berkshire vacation rental in a 10,000 acres forest

3 bedrooms·2 baths
Plainfield • Massachusetts
4.85(242 reviews)

$ 1.115,25 USD totaal voor 3 nachten

12–15 nov 2026

7 person Artesian Grand Cayman hot tub with all the bells and whistles.
The living room has a gas fireplace, smart TV, and the couch can pull out for an extra bed for large groups.
The walk-out basement has a large screen smart TV, shuffleboard, magnetic dart board, pull-out couch, an ottoman that folds out into a single bed, a woodstove, and it all leads out to the hot tub. Free firewood is just outside the door.
Great spot to have your morning coffee and catch the morning sun.
Master bedroom with flat-screen smart TV, private bathroom including bathtub and shower, closet space, dressers, an LED wall mount fireplace, and a wall unit minisplit system for heating and cooling.

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

3 bedrooms·2 baths
Otis • Massachusetts
4.84(204 reviews)

$ 936,53 USD $ 845,38 USD totaal voor 3 nachten

15–18 nov 2026

Gorgeous Sandy Priscilla Beach on Cape Cod Bay
Front view of Decks2Sea in Priscilla Beach
Front view of Decks2Sea in Priscilla Beach
Large living room with 60" Smart TV and custom leather sofa with Queen Pull out
Brand New Top of the lineAppliances

Decks2Sea

4 bedrooms·2½ baths
Plymouth • Massachusetts
5(201 reviews)

$ 4.796,60 USD totaal voor 3 nachten

12–15 nov 2026

Hygge House on Richmond Pond
Hygge House on Richmond Pond
Hygge House on Richmond Pond
Hygge House on Richmond Pond
Hygge House on Richmond Pond

Hygge House on Richmond Pond

3 bedrooms·2 baths
Richmond • Massachusetts
4.95(62 reviews)

$ 1.701,67 USD totaal voor 3 nachten

12–15 nov 2026

Sunset over the Berkshire Mountains in the distance.
Pastoral Hadley Land
Living room with 46" LED TV and Queen Pull out sofa.
Updated Entryway with Hardwood stairs.
Entryway View from front door

CountrySide close to Amherst, UMass and Noho!

4 bedrooms·2 baths
Hadley • Massachusetts
5(129 reviews)

$ 2.940,00 USD totaal voor 3 nachten

12–15 nov 2026

Berkshire Farm Sanctuary-A home of love & kindness image 1
The long and winding driveway up to the house... Aahhh, exhale...
It's a warm, cozy, wonderful life!
Christmas ready!
Cozy up with your loved ones in front of the fire!

Berkshire Farm Sanctuary-A home of love & kindness

3 bedrooms·2 baths
Hinsdale • Massachusetts
5(42 reviews)

$ 1.500,00 USD totaal voor 3 nachten

12–15 nov 2026

Nestled in scenic surroundings, just a heartbeat away from outdoor adventures
Spacious and vibrant, equipped for family entertainment and relaxation
Fire pit and Adirondack chairs in the yard
Dine al fresco on our spacious patio; perfect for enjoying morning coffee outdoors or evening conversations under the warm glow of our elegantly lit covered porch, a cozy spot for nightcaps
Sleek, modern kitchen equipped with state-of-the-art appliances and a spacious layout for culinary adventures

Berkshires Escape - ski, hike, museums, and more!

4 bedrooms·2 baths
Adams • Massachusetts
4.98(61 reviews)
$200/ nacht(excl. kosten & belastingen)
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.
Just steps from the slopes, our building sits at the base of Jiminy Peak’s 45 ski trails. Ski-in/ski-out convenience all winter long.
Winter at Jiminy Peak: Slopes, Skiers & Fireside Warmth. Ski-in/ski-out convenience meets cozy aprs-ski vibes.
Spacious bedroom/King Bed with New Mattress & Natural Light
Comfortable Open Floor Plan - Great for Long Stays!

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

1 bedroom·1 bath
Hancock • Massachusetts

$ 3.000,00 USD totaal voor 30 nachten

7 mrt – 6 apr 2027