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Holiday rentals in Sudlersville

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Popular amenities for Sudlersville holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Homes with more space

Top guest favourite
The exterior of a large, historic house is viewed from the river, surrounded by leafless trees and greenery. A deck is visible, along with a patio area featuring white chairs. The structure showcases multiple levels and a traditional architectural style.
Flat in Chestertown
5 out of 5 average rating, 130 reviews

Waterfront historic district 1BR Apartment

Top guest favourite
A serene waterfront view reveals calm water framed by lush green trees. A small private dock is visible, featuring an orange kayak resting at the edge. The scene conveys tranquility, inviting relaxation amidst nature.
Guest suite in Chestertown
4.99 out of 5 average rating, 242 reviews

Beautiful Waterfront Chestertown Getaway

Top guest favourite
A bright open living space features large windows allowing natural light to fill the room. Comfortable seating is arranged around a glass coffee table. The dining area is visible in the background, with a wooden table and chairs, connecting to a modern kitchen with stylish cabinetry.
Flat in Chestertown
4.98 out of 5 average rating, 120 reviews

Bright, new apartment in the heart of Chestertown

Top guest favourite
A cozy living area features two brown leather sofas, a patterned rug, and a soft ottoman. A reading nook is created with a gray chair draped in a yellow blanket. Natural light streams in through a large window, with plants and bookshelves enhancing the space.
Home in Chestertown
4.97 out of 5 average rating, 157 reviews

Cozy 3-bedroom home w/ Hot tub & firepit

Destinations to explore