Dorchester County rentals with pool

We found 121 rentals with pool — enter your dates for availability

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December 2025

January 2026

Explore Dorchester County rentals with pools

Magnificent property for crabbing, fishing, volleyball and badmitten

Premier Host

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Sleeps 28 · 7 bedrooms · 6+ bathrooms

Property grounds

250 ACRE RETREAT CHESAPEAKE BAY VACATION/REUNION/WEDDING 12 BEDROOMS, SLEEPS 40

Sleeps 40 · 12 bedrooms · 8+ bathrooms

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Weddings/Reunions/Corp & Private Retreats 22 Acre Chesapeake Waterfront Estate

Sleeps 60 · 20 bedrooms · 16+ bathrooms

Pool

Premier Host

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Sleeps 20 · 7 bedrooms · 5+ bathrooms

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Condo/Apartment

Rentals with Pool in Dorchester County

Holiday Rental options in Dorchester County

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