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Vacation rentals in Chestertown

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Top-rated vacation rentals in Chestertown

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

Beautiful Waterfront Chestertown Getaway
SUPERHOST
Entire guest suite · 2 guests · 2 beds · 1 bath

Beautiful Waterfront Chestertown GetawayLovely three room waterfront apartment/guest suite conveniently located minutes from historic Chestertown and Washington College. Beautiful water views, full kitchen, wooded lot, quiet neighborhood, bird watching, biking, running, kayaking. Friendly pets (comfortable with people and our medium rescue dog) are welcome. We donate 5% of proceeds to Save the Children, the Kent County Humane Society, or ShoreRivers conservation—your choice. Make it your home away from home.

Carriage House Hideaway in Middle of Chestertown
SUPERHOST
Entire rental unit · 2 guests · 1 bed · 1 bath

Carriage House Hideaway 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. Totally private 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.

The Bittersweet
Entire rental unit · 4 guests · 2 beds · 1 bath

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.

Vacation rentals for every style

Get the amount of space that is right for you.

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Popular amenities for Chestertown vacation rentals

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

Other great vacation rentals in Chestertown

SUPERHOST
  1. Entire rental unit
  2. Chestertown
RIVER WATCH
SUPERHOST
  1. Entire residential home
  2. Chestertown
Historic Chestertown
SUPERHOST
  1. Private room
  2. Chestertown
Chestertown - Eastern Shore Getaway
SUPERHOST
  1. Entire guesthouse
  2. Chestertown
Cozy Carriage House
SUPERHOST
  1. Entire cottage
  2. Chestertown
Quiet Cottage on Heron Pond
SUPERHOST
  1. Entire residential home
  2. Chestertown
Waterfront w/Pier &Walking Distance to Chestertown
SUPERHOST
  1. Entire residential home
  2. Chestertown
Merry Manor Pet Friendly Home
  1. Camper/RV
  2. Chestertown
Cozy Airstream on a beautiful horse farm
SUPERHOST
  1. Entire rental unit
  2. Chestertown
Downtown Studio Apartment
  1. Entire residential home
  2. Chestertown
Newly-Renovated Chestertown Charmer
  1. Private room
  2. Chestertown
Private Room w/bath: Walk to Washington College
SUPERHOST
  1. Entire residential home
  2. Chestertown
Wren Retweet- Country Estate in Center of C’Town

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