
Cottage vacation rentals in Berkshire County
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Top-rated cottage rentals in Berkshire County
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Berkshire County cottage rentals
Cottage rentals with a hot tub

Norte Maison 2 beds 2 Baths Minutes to Jiminy Peak

mountain refuge

A Magical Spot on Little Robin Lake

Light-filled cottage

Berkshire lakefront cabin with modern luxuries
Pet-friendly cottage rentals

Cheerful 3+ bedroom cottage with lake views

Carriage house with Chef's Kitchen, close to town

Harvey Mountain Lodge by State Forest

Berkshire Cottage Queen Bd-Jiminy Peak 3 mi

Tranquil Lake Cottage on 3 Acres with Large Deck

Pet friendly Cottage on Lake; Hike, Swim, Kayak

New! Fully renovated private cottage

Beautifully Nestled Berkshires Home
Private cottage rentals

Berkshire Cottage - Relaxation Destination

Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

Tanglewood Cottage in the heart of the Berkshires

Cozy Cottage in the Berkshires

Rustic Berkshires Cottage

Cozy Cottage in the Clouds With Mountain Views

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

Pontoosuc Lakeshore
Destinations to explore
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- Six Flags New England
- John Boyd Thacher State Park
- Taconic State Park
- Bushnell Park
- Berkshire East Mountain Resort
- Zoom Flume
- Albany Center Gallery
- Jiminy Peak Mountain Resort
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Kent Falls State Park
- Norman Rockwell Museum
- Catamount Mountain Ski Resort
- Mount Snow Ski Resort
- Beartown State Forest
- Mohawk Mountain Ski Area
- Talcott Mountain State Park
- Wintonbury Hills Golf Course
- Hartford Golf Club
- Mount Sugarloaf State Reservation
- Bousquet Mountain Ski Area
- Bright Nights at Forest Park
- Hancock Shaker Village
- Opus 40