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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.

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
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.
$149 per night
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

Other great vacation rentals in Kent County

Rental unit in Chestertown
Bright, new apartment in the heart of Chestertown
$192 per night
Guest suite in Chestertown
Historic Downtown Garden Oasis with Private Patio
$134 per night
Rental unit in Chestertown
1-br apt in downtown Chestertown
$169 per night
Home in Chestertown
Simple Living on the Pond
$103 per night
Home in Chestertown
Cozy 3-bedroom home w/ screened in porch & firepit
$184 per night
Private room in Millington
Guest Suite in a Victorian on the Chester River
$59 per night
Guesthouse in Chestertown
Cozy Carriage House
$106 per night
Home in Chestertown
$172 per night
Cabin in Chestertown
Rivershore Retreat
$291 per night
Private room in Chestertown
Historic Private Second Floor
$100 per night
Private room in Rock Hall
$62 per night
Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
$120 per night

Other types of stays on Airbnb

  1. Airbnb
  2. United States
  3. Maryland
  4. Kent County