Cecil County rentals with pool

We found 142 rentals with pool — enter your dates for availability

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September 2025

October 2025

Explore Cecil County rentals with pools

Breathtaking waterfront home- w/private pool- Booking Fall 2025 & Summer 2026

Sleeps 8 · 4 bedrooms · 2 bathrooms

Waterfront: Panoramic Views/ Pickleball coming soon/Hot Tub/ Pool/Sleeps 16

Sleeps 16 · 7 bedrooms · 5 bathrooms

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Sleeps 4 · 1 bedroom · 1 bathroom

12 Bedroom Waterfront Historic 1920 Mansion! Pool, hot tub and 400 acres!

Sleeps 30 · 12 bedrooms · 8+ bathrooms

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Rentals with Pool in Cecil County

Rentals with Pool in Cecilton

Rentals with Pool in Charlestown

Rentals with Pool in Port Deposit

Rentals with Pool in Earleville

Rentals with Pool in Elkton

Rentals with Pool in North East

Rentals with Pool in Rising Sun

Rentals with Pool in Colora

Rentals with Pool in Perryville

Rentals with Pool in Chesapeake City

Holiday Rental options in Cecil County

Family-friendly holiday rentals in Cecil County

Ski holiday rentals in Cecil County

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Holiday rentals with spa pool in Cecil County

Pet-friendly holiday rentals in Cecil County

Monthly rentals in Cecil County

Oceanfront holiday rentals in Cecil County

Lake holiday rentals in Cecil County

Beach holiday rentals in Cecil County

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