
Vacation rentals with a pool in Pioneer Valley
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Pioneer Valley
Guests agree: these homes with a pool 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 Pioneer Valley rentals with a pool
House rentals with a pool

Berkshires Oasis Retreat: Art Meets Nature

Happy Valley getaway

Serene South Deerfield Retreat

Bougie B’s Mountainside Getaway

High Field Farm

Mountain Blossom Retreat by Evergreen Home

Berkshire County modern home + pool

Spacious 4BR Central-Berkshires Home with POOL!
Condo rentals with a pool

Condo Resort at Jiminy Peak Ski Mountain's Base

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

Unique - Country suite @ Jiminy Peak

Jiminy Peak Apartment

Crafts Inn in Vermont 1br suite, Saturday check-in

Jiminy Peak Country Inn 1 Bedroom Suite

Peaceful 1BR Condo with Pond View

Wyndham Bentley Brook
Other vacation rentals with a pool

Historic Stockbridge Villa on 25 acres sleeps 16

Great place|2 BD|Kitchen| Pool

Modern 4BR Cabin, Near Lake & Mt. Snow

Berkshire Mountain House

Cabin | Chalet | Mt Snow | Hot Tub & Pool Access

Beautiful place|2 BD|Kitchen| Pool

Artsy loft near MassMoCA with pool and hot tubs

Modern Chalet-private deck/firepit/ clubhouse pool
Destinations to explore
- Plainview Vacation rentals
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- Condo rentals Pioneer Valley
- Private suite rentals Pioneer Valley
- Rentals with a patio Pioneer Valley
- House rentals Pioneer Valley
- Rentals with a kayak Pioneer Valley
- Family-friendly rentals Pioneer Valley
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- Smoking-friendly rentals Pioneer Valley
- Rentals with breakfast Pioneer Valley
- Bed and breakfasts Pioneer Valley
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- Rentals with a firepit Pioneer Valley
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- Rentals with a hot tub Pioneer Valley
- Rentals with pools Massachusetts
- Rentals with pools United States
- Six Flags New England
- Jiminy Peak Mountain Resort
- Monadnock State Park
- TPC River Highlands
- Berkshire East Mountain Resort
- Brownstone Adventure Sports Park
- Bash Bish Falls State Park
- Bushnell Park
- Brimfield State Forest
- Catamount Mountain Ski Resort
- Norman Rockwell Museum
- Bigelow Hollow State Park
- Dinosaur State Park
- Wintonbury Hills Golf Course
- Mount Greylock Ski Club
- Taconic State Park
- Mount Tom State Reservation
- Mohawk Mountain Ski Area
- Beartown State Forest
- Mount Sugarloaf State Reservation
- The Shattuck Golf Club
- Hartford Golf Club
- Hancock Shaker Village
- Talcott Mountain State Park