
House vacation rentals in Berkshire County
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Top-rated house rentals in Berkshire County
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Berkshire County house rentals
House rentals with a pool

The Catamount Ski Haus w. Pool/Hot Tub

Hillsdale 7BR | Pool | Hot tub | Game Rm | Firepit

Berkshire Mountain home views, pool, Queechy Lake

Stunning luxury home with pool

Berkshires Estate w/Heated Pool by Evergreen Home

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

Berkshire County modern home + pool

Stylish Rural Sanctuary with POOL!
Weekly house rentals

Berkshires Retreat | Fenced Yard + Near Tanglewood

Little Longbow Lakefront Chalet

Waterfront oasis in heart of Berkshires

Cozy Berkshire Getaway

Modern and Stylish Country Lakeside Cottage

Charming Cottage - Walk To Town

New Shaw Pond Skytop Retreat in the Berkshires

Berkshires Lakefront Stylish Retreat w/Gameroom
Private house rentals

Nerd Preservation Sanctuary

Cabin With a Beautiful Lake View

Private Home in The Berkshires (New Hot Tub!)

Private Lakehouse in the heart of the Berkshires

The Little Yellow Door

Lux on the River near Tanglewood w/220v EV charge

Berkshire Lakefront Lighthouse Getaway

NEW! Hilltop Ski and Sun Chalet with Hot Tub
Destinations to explore
- Rentals with lake access Berkshire County
- Cabin rentals Berkshire County
- Rentals with a hot tub Berkshire County
- Bed and breakfasts Berkshire County
- Rentals with a sauna Berkshire County
- Rentals with a patio Berkshire County
- Beachfront rentals Berkshire County
- Kid-friendly rentals Berkshire County
- Rentals with pools Berkshire County
- Rentals with breakfast Berkshire County
- Private suite rentals Berkshire County
- Cottage rentals Berkshire County
- Fitness-friendly rentals Berkshire County
- Rentals with a kayak Berkshire County
- Chalet rentals Berkshire County
- Ski-in/ski-out rentals Berkshire County
- Condo rentals Berkshire County
- Rentals with outdoor seating Berkshire County
- Waterfront rentals Berkshire County
- Rentals with an EV charger Berkshire County
- Rentals with beach access Berkshire County
- Family-friendly rentals Berkshire County
- Rentals with a washer and dryer Berkshire County
- Rentals with a fire pit Berkshire County
- Pet-friendly rentals Berkshire County
- Apartment rentals Berkshire County
- Guesthouse rentals Berkshire County
- Farmstay rentals Berkshire County
- Rentals with a fireplace Berkshire County
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- Six Flags New England
- John Boyd Thacher State Park
- Albany Center Gallery
- Bushnell Park
- Jiminy Peak Mountain Resort
- Taconic State Park
- Berkshire East Mountain Resort
- Catamount Mountain Ski Resort
- Zoom Flume
- Kent Falls State Park
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Norman Rockwell Museum
- Mohawk Mountain Ski Area
- Beartown State Forest
- Bright Nights at Forest Park
- Hartford Golf Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Opus 40
- Naumkeag
- Brignole Vineyards
- Bousquet Mountain Ski Area