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Holiday rentals in Chestertown

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Top-rated holiday rentals in Chestertown

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

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.
The Bittersweet
Entire rental unit · 4 guests · 2 beds · 1 bathroom
The BittersweetA spacious private apartment right in the heart of beautiful downtown Chestertown! With food, drinks, and shopping literally steps from your front door, it doesn't get better than this. The Bittersweet Apartment is a subsidy of The White Swan Tavern.
Downtown Studio Apartment
SUPERHOST
Entire rental unit · 2 guests · 1 bed · 1 bathroom
Downtown Studio ApartmentStudio apartment right in the heart of downtown Chestertown overlooking Fountain Park. Close to downtown shops and restaurants and Saturday Farmers market

Holiday rentals for every style

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Popular amenities for Chestertown holiday rentals

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

Other great holiday rentals in Chestertown

SUPERHOST
  1. Entire guest suite
  2. Chestertown
Beautiful Waterfront Chestertown Getaway
SUPERHOST
  1. Private room
  2. Chestertown
Chestertown - Eastern Shore Getaway
SUPERHOST
  1. Entire residential home
  2. Chestertown
Merry Manor Pet Friendly Home
SUPERHOST
  1. Entire cabin
  2. Chestertown
Rivershore Retreat
SUPERHOST
  1. Entire rental unit
  2. Chestertown
1-br apt in downtown Chestertown
SUPERHOST
  1. Entire residential home
  2. Chestertown
Wren Retweet- Country Estate in Center of C’Town
  1. Entire cottage
  2. Chestertown
Chestertown's Little Red Cottage, Pet-Friendly
SUPERHOST
  1. Entire rental unit
  2. Chestertown
RIVER WATCH
SUPERHOST
  1. Private room
  2. Chestertown
Private Room w/bath: Walk to Washington College
SUPERHOST
  1. Entire residential home
  2. Chestertown
Classic Victorian in Chestertown
SUPERHOST
  1. Entire residential home
  2. Chestertown
Town House in the Heart of Chestertown
  1. Entire residential home
  2. Chestertown
Historic downtown Chestertown Home. #1 Location.