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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.
$98 per night
Rental unit in Chestertown
Bright, new apartment in the heart of Chestertown
Flooded with light and in the center of all Chestertown has to offer. Directly across the street from Evergrain Bakery. The apartment spans the entire front of the second floor of the recently restored building, built in 1877. Open living room/dining area/kitchen. Historic character with all modem conveniences, including dishwasher, washer/dryer, Smart TV and high speed wifi internet access. Off-street parking for one car on first come first served basis with ample street parking.
$156 per night
Serviced apartment in Chestertown
Waterfront historic district 1BR Apartment
Take it easy at this unique and tranquil getaway. Third floor, one bedroom apartment with its own private rooftop deck and beautiful views of the Chester River. Located at the end of a street on the water but still in the historic district offering convenience and privacy. A short stroll to everything Chestertown has to offer. Off street parking. Kayaks or canoe available with notice or bring your own. Enjoy coffee and sunrise from deck or Adirondacks. NO CLEANING FEE!
$156 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 Wilmer Park
Wilmer Park4 locals recommend

Other great vacation rentals in Chestertown

Guesthouse in Chestertown
Cozy Carriage House
$101 per night
Guest suite in Chestertown
Downtown Garden Oasis w/ Private Patio!
$109 per night
Private room in Chestertown
Chestertown - Eastern Shore Getaway
$129 per night
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
$109 per night
Home in Chestertown
Cozy 3-bedroom home w/ screened in porch & firepit
$173 per night
Home in Chestertown
$161 per night
Private room in Millington
Guest Suite in a Victorian on the Chester River
$59 per night
Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
$120 per night
Home in Chestertown
Simple Living on the Pond
$103 per night
Home in Chestertown
2 Beds, 2.5 Baths, Perfect Downtown Location
$159 per night
Cabin in Chestertown
Rivershore Retreat
$276 per night
Cottage in Chestertown
Chestertown's Little Red Cottage, Pet-Friendly
$235 per night
  1. Airbnb
  2. United States
  3. Maryland
  4. Kent County
  5. Chestertown