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
$100/ night(excl. fees & taxes)
Jiminy Peak Slopeside Getaway • Ski & Adventure
Jiminy Peak Slopeside Getaway • Ski & Adventure
Jiminy Peak Slopeside Getaway • Ski & Adventure
Jiminy Peak Slopeside Getaway • Ski & Adventure
Jiminy Peak Slopeside Getaway • Ski & Adventure

Jiminy Peak Slopeside Getaway • Ski & Adventure

2 bedrooms·2 baths
Hancock • Massachusetts

$682.86 USD total for 3 nights

Sep 7 – 10, 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 total for 3 nights

Sep 13 – 16, 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/ night(excl. fees & taxes)
Condo near Mass Moca
Condo near Mass Moca
Condo near Mass Moca
Condo near Mass Moca
Condo near Mass Moca

Condo near Mass Moca

3 bedrooms·2 baths
North Adams • Massachusetts
4.83(6 reviews)

$940.00 USD total for 3 nights

Sep 7 – 10, 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 total for 3 nights

Sep 7 – 10, 2026

Free cancellation
View of the Property
Dining room
Dining room
Kitchen
Kitchen

Plainfield House

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

$1,066.10 USD total for 3 nights

Sep 12 – 15, 2026

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.
The acre lot has plenty of room for tossing a football or a game of soccer.
Berkshires Fall Escape with Views & Cozy Fireplace image 3
Berkshires Fall Escape with Views & Cozy Fireplace image 4
Berkshires Fall Escape with Views & Cozy Fireplace image 5

Berkshires Fall Escape with Views & Cozy Fireplace

3 bedrooms·2½ baths
Great Barrington • Massachusetts
5(28 reviews)
$271 – $595/ night(excl. fees & taxes)
Ruins of Ashintully, 1/4 mile walk up hill from the cottage
Ashintully Cottage, front view from Sodom Road.
Back view: cottage is across the street from the Ashintully Gardens.
Cottage is surrounded by land under conservation restriction, with hiking trails
Cottage is bright and filled with light from all directions.

Ashintully Cottage

4 bedrooms·3 baths
Tyringham • Massachusetts
5(45 reviews)

$1,426.95 USD total for 3 nights

Sep 7 – 10, 2026

Berkshires Cottage | Trails & Water Nearby
Berkshires Cottage | Trails & Water Nearby
Berkshires Cottage | Trails & Water Nearby
Berkshires Cottage | Trails & Water Nearby
Fully stocked eat-in kitchen

Berkshires Cottage | Trails & Water Nearby

2 bedrooms·1 bath
Monterey • Massachusetts

$557.60 USD total for 3 nights

Sep 7 – 10, 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)

$953.28 USD $913.91 USD total for 3 nights

Sep 7 – 10, 2026