
Holiday rentals with a pool in Chester County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Chester County
Guests agree: these homes with a pool 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 Chester County rentals with a pool
House rentals with a pool

Contractors Love Us! Like Vacation while working

Whitehorse view of Amish country

Cozy 4BR Parkesburg Home with Pool & Sunroom

Family home with Pool, Hot-tub & Pickleball court!

New Pristine Suburban Escape

Modern Farmhouse: Pool, Hot Tub & Pickleball

Comfort, Fun, & charming! - 5BR oasis w/ Pool

Happy Trails Guest House “private pool & hot tub”
Other holiday rentals with a pool

Sonoma Tiny Home at Red Run - Site 104

Creekfront Glamping Pod - Site 42

Ask about long term!

Waterfront A-Frame Studio at Red Run - Site 138

Waterfront A-Frame Studio at Red Run - Site 137

Waterfront A-Frame Tiny Home at Red Run - Site 116

King of the hill

Waterfront A-Frame Studio at Red Run - Site 139
Destinations to explore
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- Rentals with pools Pennsylvania
- Rentals with pools United States
- Pennsylvania Convention Center
- Lincoln Financial Field
- Hersheypark
- Citizens Bank Park
- Dorney Park & Wildwater Kingdom
- Fairmount Park
- Longwood Gardens
- Betterton Beach
- Penn's Landing
- Philadelphia Museum of Art
- Diggerland
- 30th Street Station
- Marsh Creek State Park
- French Creek State Park
- Aronimink Golf Club
- Philadelphia Zoo
- The Franklin Institute
- Wissahickon Valley Park
- Crystal Beach Manor, Earleville, MD
- Wells Fargo Center
- Independence Hall
- Valley Forge National Historical Park
- Franklin Square
- Philadelphia Cricket Club