
Holiday rentals with a pool in Berkshire County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Berkshire County
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Berkshire County rentals with a pool
House rentals with a pool

Berkshires Oasis Retreat: Art Meets Nature

Berkshire Mountain House

Hillsdale Escape | Pool, Hot Tub, Game Room

Berkshire Lakefront Home W/Pool-100%Renovated

Berkshire Lake House, gunite pool, Chef's Kitchen

10 Acre Country Estate with Pool, Hot Tub & Views!

Family Lodge at Jiminy Peak - Pools & Adventure

Summer Chalet w/ Pool + Private Hiking Trails
Apartment rentals with a pool

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

Wyndham Bentley Brook - 2 BR Deluxe - Sleeps 8

Unique - Country suite @ Jiminy Peak

Jiminy Peak Country Inn 1 Bedroom Suite

Peaceful 1BR Condo with Pond View

Wyndham Bentley Brook

Jiminy Peak Country Inn - ski in/out condo MT view

Ski-in/Ski-Out on Jiminy Peak
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
- Albany Center Gallery
- Jiminy Peak Mountain Resort
- Zoom Flume
- Bash Bish Falls State Park
- Kent Falls State Park
- Catamount Mountain Ski Resort
- Norman Rockwell Museum
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Beartown State Forest
- Hartford Golf Club
- Mohawk Mountain Ski Area
- Wintonbury Hills Golf Course
- Bright Nights at Forest Park
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Opus 40
- Pineridge Cross Country Ski Area
- Naumkeag