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Vacation rentals in Kent County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Kent County

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

Superhost
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 Tolchester Marina featuring live music, dining and its own beach. One mile from a private community boat ramp to launch your water toys. 800 sq ft 2 bedroom 1 bath house is on Maryland’s Eastern Shore less than 2 hours from Washington, Baltimore and Philadelphia.
$150 per night
Superhost
Apartment in Chestertown
Secluded Cottage in Middle of Chestertown
Escape to a secluded, romantic studio getaway in the middle of Chestertown. Private parking, and over 1 acre of gardens to call your own. Relax in front of the fire with views of gardens in every window. Kitchenette has extra large toaster oven, (can cook pizza and roast chicken), 2 burner hot plate, microwave, refrigerator, plus Keurig/coffee makers. Comfortable king bed with luxury linens, kitchenette, and washer dryer. We also host ‘Wren Retweet”, a house in front of the carriage house.
$111 per night
Superhost
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
"A little slice of Americana" (commented one of our guests) This century-old three-story home is in the beautiful historic district of Chestertown, which sits on the majestic, unspoiled Chester River, on Maryland's famous Eastern Shore. We are right across the street from Washington College and just blocks from the quaint ambiance of High Street. The commercial district is equally accessible, with banks, grocery and liquor stores, restaurants, and more, a few blocks up Washington Avenue.
$119 per night

Other great vacation rentals in Kent County

Superhost
Cabin in Chestertown
Rivershore Retreat
$287 per night
Superhost
Farm stay in Chestertown
Blue Heron Farm Waterfront Chalet
$296 per night
Superhost
Cottage in Rock Hall
The Blissful Retreat @theblissfulretreat
$240 per night
Superhost
Apartment in Chestertown
Bright, new apartment in the heart of Chestertown
$175 per night
Superhost
Apartment in Chestertown
Waterfront historic district 1BR Apartment
$156 per night
Superhost
Apartment in Chestertown
Downtown Studio Apartment
$156 per night
Superhost
Guest suite in Chestertown
Historic Downtown Garden Oasis with Private Patio
$160 per night
Superhost
Home in Chestertown
Harbor View Haven | Waterfront w/ HOT TUB + Dock!
$232 per night
Superhost
Apartment in Chestertown
1-br apt in downtown Chestertown
$206 per night
Superhost
Home in Chestertown
2 Beds, 2.5 Baths, Perfect Downtown Location
$186 per night
Superhost
Cabin in Goldsboro
Wigwam Lodge~Hot Tub~MasterSuite~Woodland Views
$176 per night
Superhost
Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
$96 per night

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