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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.

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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Other great vacation rentals in Tolchester Beach

Private room in Worton
Home Farm - The Nest
$75 per night
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Cabin in Abingdon
The Fox Cabin - Perfect to Relax
$79 per night
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Home in Chestertown
Cozy 3-bedroom home w/ screened in porch & firepit
$165 per night
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Rental unit in Baltimore
Cozy Studio Apartment
$45 per night
Home in Kent Narrows
Chester Riverfront At Kent Narrows
$239 per night
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Rental unit in Downtown Baltimore
Upscale Modern Condo near downtown
$89 per night
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Home in Rock Hall
Cozy 1920's Bungalow Near Water/Local Attractions
$160 per night
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Townhouse in Joppatowne
Cozy and spacious lower level of newly built home
$48 per night
Loft in Fells Point
Historic Bank Fells Point
$106 per night
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Guest suite in Arnold
Pet Friendly King Suite, Pool/Hottub, by Annapolis
$94 per night
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Cottage in Rock Hall
Cottage with Modern Updates - Walk to Waterfront!
$153 per night
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Rental unit in Edgemere
The Sparrows Nest - in downtown Sparrows Point
$79 per night
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