
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

Workers Love Us! Like Vacation while working

Quiet Country Home in Parkesburg, In Ground Pool

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
Other holiday rentals with a pool

Fall days in the country!

Waterfront A-Frame Studio at Red Run - Site 138

Cottage

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

King of the hill

Waterfront A-Frame Studio at Red Run - Site 139

Pool still open & water near 80! Pet allowed stay!

Lovely One Bedroom Suite
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
- Dutch Wonderland
- Betterton Beach
- Penn's Landing
- Philadelphia Museum of Art
- Diggerland
- 30th Street Station
- Marsh Creek State Park
- French Creek State Park
- Aronimink Golf Club
- The Franklin Institute
- Philadelphia Zoo
- Wissahickon Valley Park
- Crystal Beach Manor, Earleville, MD
- Valley Forge National Historical Park
- Independence Hall
- Franklin Square
- Philadelphia Cricket Club