Vacation rentals in Chestertown

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Top-rated vacation rentals in Chestertown

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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

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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

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