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.

$2,620 MXN 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.

$2,100 MXN per night

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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

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