Vacation rentals in Chestertown, MD

This two-bedroom, two-bathroom rental is located in historic Chestertown, just a two-minute walk to the High Street Wharf.
This pet-friendly apartment accommodates up to five guests and features air conditioning, internet, and parking, making it an ideal base for enjoying Chestertown's festivals and river activities.

This 2-bedroom, 2-bathroom apartment in Chestertown is located within a 15-minute walk of the Kent County Historical Society and Wilmer Park, and a short distance to the Garfield Center for the Arts at the Prince Theater.
This 970 sq ft vacation home accommodates up to 6 guests and features a private garden, terrace, barbecue, air conditioning, Wi-Fi, a full kitchen, and on-site parking.

This charming house is situated in Chestertown's historic district, just a short walk from Washington College and the waterfront. The property consistently receives excellent ratings for its location, cleanliness, and overall experience.
This 5-bedroom home can accommodate up to 10 guests and offers two primary suites, a loft, and three additional bedrooms. The house features modern conveniences, a spacious fenced yard, a well-equipped kitchen, fast internet, and access to over an acre of gardens, making it perfect for families or groups looking for a comfortable and private stay.

This Chestertown apartment rental is centrally located, within a 10-minute walk of River Arts Chestertown, the Garfield Center for the Arts, the Historical Society of Kent County, Wilmer Park, and Washington College.
This 520-square-foot unit features one bedroom, one bathroom, accommodates two guests, and includes a kitchenette with a refrigerator and microwave, a private fenced yard, a balcony, free Wi-Fi, and on-site parking.