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

$749.18 USD total for 3 nights

Oct 30 – Nov 2, 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

$629.25 USD total for 3 nights

Oct 30 – Nov 2, 2026

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

Oct 30 – Nov 2, 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 $860.12 USD total for 3 nights

Nov 1 – 4, 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(30 reviews)

$8,892.00 USD total for 32 nights

Dec 1, 2026 – Jan 2, 2027

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

Oct 30 – Nov 2, 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

Oct 30 – Nov 2, 2026