Vacation rentals in Chestertown

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Top-rated vacation rentals in Chestertown

Guests agree: these vacation rentals 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.
$2,620 MXN per night
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.
$2,100 MXN per night
Rental unit in Chestertown
1-br apt in downtown Chestertown
1-bedroom newly-renovated apartment located in a 5-unit apartment building near downtown Chestertown, MD. Unit 1 is located two blocks from High Street (think Evergrain Bakery!) and about four blocks from the Chester River. Enjoy a shared front porch with the other long-term tenants, or use the private back porch to sit and read the newspaper or enjoy the outside.
$3,161 MXN per night

Stay near Chestertown's top sights

Photo of Fish Whistle
Fish Whistle23 locals recommend
Photo of Luisa's Cucina Italiana
Luisa's Cucina Italiana27 locals recommend
Photo of Procolino's Pizza
Procolino's Pizza15 locals recommend
Photo of ACME Markets
ACME Markets13 locals recommend
Photo of 98 Cannon Riverfront Grille
98 Cannon Riverfront Grille11 locals recommend
Photo of Uncle Charlie's Bistro
Uncle Charlie's Bistro15 locals recommend

Other great vacation rentals in Chestertown

Guest suite in Chestertown
Historic Downtown Garden Oasis with Private Patio
$2,433 MXN per night
Home in Chestertown
$3,437 MXN per night
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
$2,075 MXN per night
Home in Chestertown
Merry Manor Pet Friendly Home
$2,179 MXN per night
Private room in Chestertown
Historic Private Second Floor
$1,743 MXN per night
Guesthouse in Chestertown
Cozy Carriage House
$1,756 MXN per night
Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
$2,092 MXN per night
Serviced apartment in Chestertown
Waterfront historic district 1BR Apartment
$2,797 MXN per night
Rental unit in Chestertown
Bright, new apartment in the heart of Chestertown
$3,138 MXN per night
Home in Chestertown
Cozy 3-bedroom home w/ screened in porch & firepit
$3,121 MXN per night
Home in Chestertown
2 Beds, 2.5 Baths, Perfect Downtown Location
$3,395 MXN per night
Private room in Worton
Home Farm - The Nest
$1,308 MXN per night

Other types of stays on Airbnb

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