Vacation rentals in Tolchester Beach

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Top-rated vacation rentals in Tolchester Beach

Guests agree: these stays are highly rated for location, cleanliness, and more.

SUPERHOST

Home in Chestertown

Cape Cod | Wknd Access 2 Beach & Bike to Rock Hall

Walk to the beach! Home with 2000 sq ft, quality built w/ space for your boat. Large open kitchen; back door leads to deck w/ cushion seats, grill, games & more. The home is 10 mins from Great Oak Manor, Washington College & 35 miles from 4 wineries. Relax around the fire pit or fireplace w/ hot chocolate & s'mores. 9 spaces to enjoy. Take in all nature has to offer watching deer, bald eagles, birds & rabbits. 12 minute drive to downtown Chestertown 3 blocks from the beach (May. - Oct.)

$296 per night

SUPERHOST

Serviced apartment in Chestertown

Waterfront historic district 1BR Apartment

Take it easy at this unique and peaceful riverfront getaway. Third floor, one bedroom apartment with its own private rooftop deck and beautiful views of the Chester River. Located at the end of a street on the water, but still in the historic district offering convenience and privacy. A short stroll to everything Chestertown has to offer. Off street parking. Kayaks or canoe available with notice or bring your own. Enjoy coffee and sunrise from deck or Adirondacks. NO CLEANING FEE!

$156 per night

Private room in Rock Hall

Treetops

At the peak of this charming 1880 Victorian this cozy room will provide a quiet getaway. Located only a mile from town. This room is Hidden away on the top floor (3rd), nestled amongst the tree tops. Prime Features are Private bathroom and kitchenette, matching lazy boy chairs and super comfy bed. Equipped with a double sink, small fridge, microwave, hot and cold water dispenser and a coffee maker. Comfort and peace is what you will encounter on your stay here.

$61 per night