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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.

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.
$144 per night
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Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
Lovely 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 Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice. Make it your home away from home.
$120 per night
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Private room in Millington
Guest Suite in a Victorian on the Chester River
Our lovingly-restored Millington Manor is the original home of the local doctor, built in 1868. Our small town has a liquor store and grocery. We are a 15-minute ride to Chestertown, home of Washington College and host to wonderful restaurants, lovely shops, galleries and a theatre. Crumpton's auction is minutes away.
$59 per night
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Other great vacation rentals in Kent County

Home in Chestertown
CHESAPEAKE SUNSETS
$199 per night
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Rental unit in Chestertown
1-br apt in downtown Chestertown
$182 per night
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Guest suite in Chestertown
Historic Downtown Garden Oasis with Private Patio
$139 per night
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Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
$119 per night
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Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
$120 per night
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Guest suite in Joppatowne
Cozy, clean & spacious lower level of a new home
$62 per night
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Private room in Chestertown
Historic Private Second Floor
$100 per night
Serviced apartment in Chestertown
Waterfront historic district 1BR Apartment
$160 per night
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Private room in Worton
Home Farm Retreat
$100 per night
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Private room in Millington
Historic Crumpton Victorian by the Chester River
$85 per night
Private room in Chestertown
Private Bedroom and bath in Chestertown, MD
$65 per night
Home in Church Hill
Private Peaceful Waterfront House w/ Pool, Hot Tub
$539 per night
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Other types of stays on Airbnb

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