Vacation rentals in Tolchester Beach

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Top-rated vacation rentals in Tolchester Beach

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Home in Chestertown

CHESAPEAKE SUNSETS

Escape to a quaint bayside cottage with sweeping views of the Chesapeake. Relax and enjoy beautiful sunsets from the bayside sundeck, screened porch or from the comfort of your home. Less than 2 miles to the seasonal Shanty Bar at Tollchester Marina featuring live music, dining and its own beach or a private community boat ramp to launch your water toys. This 800 sq ft 2 bedroom 1 bath house is located on Maryland’s Eastern Shore less than 2 hours from Washington, Baltimore and Philadelphia.

$146 per night

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Home in Chestertown

Modern Decor Home w/ Fireplace, Deck & Workspace

Home is located in an Oceanfront Community is 10 minutes from Great Oak Manor, Washington College, Rock Hall & 35 miles from 4 wineries. Relax w/ family & friends around the fire pit or fireplace w/ hot chocolate and s'mores. Nine spaces for you to enjoy. Access the deck w/ cushion seats, grill, games and more. Take in all nature has to offer watching deer, bald eagles, birds & rabbits. You are: 10 to 15 minute drive to Historic District Chestertown 3 blocks from the beach (May. - Oct.)

$247 per night

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Rental unit in Chestertown

Secluded Cottage in Middle of Chestertown

Escape to a secluded, romantic studio getaway in the middle of Chestertown. Private parking, and over an acre of gardens to call your own. Enjoy the fire with views of nature all around, this is the perfect place to relax. Kitchenette has extra large toaster oven, (can cook pizza and roast chicken), 2 burner hot plate, microwave, refrigerator, and coffee maker. Comfortable queen bed, kitchenette, and washer dryer. We also host ‘Wren Retweet”, a large house in front of the carriage house.

$120 per night

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