Maryland family rentals

We found 11,702 family rentals — enter your dates for availability

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November 2025

9

December 2025

Find the best place to stay - Maryland

Magnificent property for crabbing, fishing, volleyball and badmitten

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

Pool

Premier Host

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

Sleeps 20 · 7 bedrooms · 5+ bathrooms

Exterior

Premier Host

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Sleeps 16 · 5 bedrooms · 4+ bathrooms

Find spaces that suit your style

House

Condo/Apartment

Holiday Rental options in Maryland

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