
Holiday rentals with a pool in Cecil County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Cecil 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 Cecil County rentals with a pool
House rentals with a pool

Chestertown Watson Family Farm

Breathtaking Waterfront Now booking Fall 2025

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

Charming 3 Bedroom with a Pool

The Hidden Gem•Heated pool•Pickleball Court

Spacious 4-bedroom house with a private pool.

Waterfront Poolside Escape

The Peaceful Getaway (with private pool & hot tub)
Condo rentals with a pool

Family Friendly 2B2B one level Condo in Pike Creek

Beach Haven Hideout

3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!

Best kept secret beach-condo on the Chesapeake Bay
Other holiday rentals with a pool

Chesapeake East Shore Chestertown,Pool (May1),Dock

Cozy, Cute and Clean rowhouse w/ 2 Masters!

Carriage House in Landenberg

Historic Victorian Queen Chesapeake City

Pool House by the North East River

Cording Lodge*Pool*Pickleball/Basketball court

Eagle Bunkhouse

Scenic 5BD 3.5BA Home Short Distance to Airport
Destinations to explore
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- Rentals with pools Maryland
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- Pennsylvania Convention Center
- Lincoln Financial Field
- Citizens Bank Park
- Fortescue Beach
- Oriole Park at Camden Yards
- Fairmount Park
- Dutch Wonderland
- Betterton Beach
- Longwood Gardens
- Penn's Landing
- M&T Bank Stadium
- Sandy Point State Park
- Philadelphia Museum of Art
- Hampden
- 30th Street Station
- Patterson Park
- The Franklin Institute
- Caves Valley Golf Club
- Aronimink Golf Club
- Marsh Creek State Park
- Philadelphia Zoo
- French Creek State Park
- Crystal Beach Manor, Earleville, MD
- Franklin Square