
House holiday rentals in Berkshire County
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Top-rated house rentals in Berkshire County
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Holiday rentals for every style
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Popular amenities for house rentals in Berkshire County
House rentals with a pool

Berkshires Oasis Retreat: Art Meets Nature

The Catamount Ski Haus with Pool & Hot Tub

Berkshire Mountain home views, pool, Queechy Lake

Stunning luxury home with pool

Mountain Blossom Retreat by Evergreen Home

Red Rock Summit: Mtn Escape w/ Pool, Pond + Views

Hilltop: Panoramic Views w/ Pool near Catamount

Berkshire County modern home + pool
Weekly house rentals

Waterfront Modern Lake Mansfield Retreat

Waterfront oasis in heart of Berkshires

Charming Cottage - Walk To Town

Berkshires Lakefront Stylish Retreat w/Gameroom

NEW! Hilltop Ski and Sun Chalet with Hot Tub

The Berkshires Hummingbird House

Relaxing Berkshire Retreat with Lake Access

Private Getaway on large acreage
Private house rentals

Berkshires Retreat | Fenced Yard + Near Tanglewood

Little Longbow Lakefront Chalet

Cabin With a Beautiful Lake View

Modern and Stylish Country Lakeside Cottage

Private Berkshires Estate w/ Tennis Court

Majestic Mountain Side FAB. Bardominium Sheffield

The Kellogg House in the Heart of The Berkshires

Tranquil 3-BR Waterfront Retreat
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