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Vacation rentals in Kent County

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Top-rated vacation rentals in Kent County

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

Home in Chestertown
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.
$141 per night
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
Townhouse in Joppatowne
Cozy and spacious lower level of newly built home
This is a roomy lower level of a newly built home, located not far from White Marsh/The Ave, Baltimore, and Towson, is ideal for two adults (plus kids upon request). Only minutes away from grocery, pizzeria, gas, Walgreens, and Gunpowder River for boating, fishing, and trails. This decorated space includes a smart TV, comfortable seating, dining for 4, microwave, coffee maker, full refrigerator, toaster/air fryer, queen bed, wardrobe and dresser. Washer/dryer available upon request.
$48 per night

Other great vacation rentals in Kent County

Guesthouse in Centreville
Centreville Cottage
$160 per night
Vacation home in Rock Hall
“Glanville” Contemporary Ranch on Chesapeake Bay
$307 per night
Home in Chestertown
Merry Manor Pet Friendly Home
$125 per night
Private room in Worton
Home Farm - The Nest
$75 per night
Home in Chestertown
Cozy 3-bedroom home w/ screened in porch & firepit
$165 per night
Rental unit in Chestertown
1-br apt in downtown Chestertown
$150 per night
Serviced apartment in Chestertown
Hillside Waterfront historic district 1BR Apt.
$152 per night
Guesthouse in Chestertown
Cozy Carriage House
$101 per night
Cottage in Kennedyville
NEW! Family-Friendly Cottage, Walk to the Beach!
$181 per night
Home in Chestertown
Simple Living on the Pond
$103 per night
Rental unit in Chestertown
Downtown Studio Apartment
$120 per night
Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
$100 per night
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