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Holiday rentals in Kent County

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Top-rated holiday rentals in Kent County

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

Secluded Cottage  in Middle of Chestertown
SUPERHOST
Entire rental unit · 2 guests · 1 bed · 1 bathroom
Secluded Cottage in Middle of ChestertownEscape 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.
Home Farm Retreat
SUPERHOST
Private room · 2 guests · 1 bed · 1 private bathroom
Home Farm RetreatIdeally situated well off the road in the middle of a working farm yet close to town for shopping and dining. It is a great retreat for a writer, a painter or a musician space with enough space to create. Private key code for access. Near marinas, parks, and charming Eastern Shore villages. Killer sunset views. Pet friendly. Out the door for wonderful and challenging country road bike rides with little to no traffic. A large fire pit and a private sitting room/gathering space.
Newly-Renovated Chestertown Charmer
SUPERHOST
Entire residential home · 4 guests · 1 bed · 1 bathroom
Newly-Renovated Chestertown CharmerWelcome to charming Chestertown. This newly-renovated one-bedroom home is located in downtown Chestertown and is walkable to many restaurants, shops, and the water. Relax in this cozy space with all-new furniture and kitchen amenities. Enjoy the deck in the back with gas fireplace and grill. This home is perfect to enjoy all the spectacular aspects of small town living.

Holiday rentals for every style

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Popular amenities for Kent County holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Kent County

SUPERHOST
  1. Entire residential home
  2. Stevensville
Love Point Idyll - 240' Private Beachfront
  1. Farm stay
  2. Chestertown
Blue Heron Farm Waterfront Chalet
SUPERHOST
  1. Entire guest house
  2. Chestertown
Cozy Carriage House
SUPERHOST
  1. Private room
  2. Millington
Guest Suite in a Victorian on the Chester River
SUPERHOST
  1. Entire guest suite
  2. Chestertown
Beautiful Waterfront Chestertown Getaway
SUPERHOST
  1. Entire rental unit
  2. Chestertown
Downtown Studio Apartment
  1. Entire residential home
  2. Rock Hall
Entire studio
SUPERHOST
  1. Entire residential home
  2. Galena
Sweet and "Sassy"-4 Bedroom 2 Bath River Home
SUPERHOST
  1. Entire residential home
  2. Chestertown
Wren Retweet- Country Estate in Center of C’Town
SUPERHOST
  1. Entire residential home
  2. Rock Hall
Pirates Perch
SUPERHOST
  1. Entire residential home
  2. Chestertown
Entire River Front Home - 4 Bedrooms 4.5 Baths
SUPERHOST
  1. Entire cottage
  2. Rock Hall
Cottage with Modern Updates - Walk to Waterfront!