
Cottage holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for cottage rentals in Berkshire County
Cottage rentals with a hot tub

Norte Maison 2 beds 2 Baths Minutes to Jiminy Peak

mountain refuge

All season fun in the Berkshires

A Magical Spot on Little Robin Lake

Light-filled cottage

Berkshire lakefront cabin with modern luxuries
Pet-friendly cottage rentals

Chic Cottage at Richmond Pond

Charming Home in Lee

Plan your Berkshires by the lake

Cheerful 3+ bedroom cottage with lake views

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

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

Tanglewood Cottage in the heart of the Berkshires

Lakefront Cottage Jiminy Ice Fishing Berkshire

Artist Retreat in Lake Community

Rustic Berkshires Cottage

Cozy Cottage in the Clouds With Mountain Views

Pontoosuc Lakeshore

Modern one bed room cottage loft on beautiful Lake
Destinations to explore
- Rentals with pools Berkshire County
- Aparthotel rentals Berkshire County
- Rentals with a patio Berkshire County
- Waterfront rentals Berkshire County
- House rentals Berkshire County
- Guest house rentals Berkshire County
- Bed and breakfasts Berkshire County
- Rentals with breakfast Berkshire County
- Rentals with a sauna Berkshire County
- Flat rentals Berkshire County
- Rentals with lake access Berkshire County
- Cabin rentals Berkshire County
- Rentals with a hot tub Berkshire County
- Hotel rentals Berkshire County
- Rentals with a firepit Berkshire County
- Rentals with a kayak Berkshire County
- Fitness-friendly rentals Berkshire County
- Private suite rentals Berkshire County
- Apartment rentals Berkshire County
- Rentals with outdoor seating Berkshire County
- Rentals with a fireplace Berkshire County
- Rentals with an EV charger Berkshire County
- Farm stay rentals Berkshire County
- Family-friendly rentals Berkshire County
- Rentals with a washing machine and dryer Berkshire County
- Ski-in/ski-out rentals Berkshire County
- Beachfront rentals Berkshire County
- Rentals with beach access Berkshire County
- Chalet rentals Berkshire County
- Pet-friendly rentals Berkshire County
- Cottage rentals Massachusetts
- Cottage rentals United States
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- John Boyd Thacher State Park
- Bash Bish Falls State Park
- Zoom Flume
- Bushnell Park
- Kent Falls State Park
- Catamount Mountain Ski Resort
- Mount Greylock Ski Club
- Wintonbury Hills Golf Course
- Norman Rockwell Museum
- Taconic State Park
- Mount Sugarloaf State Reservation
- Mount Tom State Reservation
- Opus 40
- Mohawk Mountain Ski Area
- Beartown State Forest
- Albany Center Gallery
- Talcott Mountain State Park
- Bright Nights at Forest Park
- Bousquet Mountain Ski Area
- Berkshire Botanical Garden
- Mount Snow Ski Resort