Kennedyville beach rentals

We found 13 beach rentals — enter your dates for availability

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September 2025

October 2025

Explore Kennedyville beach rentals

Kennedyville Vacation Rental | 2BR | 1BA | 4 Stairs to Access | 1,000 Sq Ft

Family-Friendly Cottage, Walk to the Beach!

Sleeps 6 · 2 bedrooms · 1 bathroom

Great room with lots of windows and beautiful views of Stillpond.

Premier Host

Waterfront Home Private Dock, Boat,fish,Eastern shore, Betterton,Chestertown

Sleeps 12 · 4 bedrooms · 2 bathrooms

EASTERN SHORE Maryland --2 minute walk to beach; Quintessential beach home

Sleeps 11 · 6 bedrooms · 2 bathrooms

Betterton Beachhouse - historic Buena Vista, overlooking the Chesapeake Bay

Premier Host

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Sleeps 10 · 5 bedrooms · 2+ bathrooms

Premier Host

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

Sleeps 3 · 1 bedroom · 1 bathroom

Premier Host

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

Sleeps 10 · 3 bedrooms · 2 bathrooms

Top rated beach rentals - Kennedyville

Premier Host

Amazing sunsets

Property was absolutely beautiful right by the water. The sunsets didn’t disappoint. Loved the little bar/restaurant that was within walking distance. Very friendly property owners & neighbors were just as friendly.

Tara B.

Stayed Sept 2024

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