Find short term rentals in Chestertown, MD at the best prices

This three-bedroom apartment is located on the third floor of Portside Manor, offering a peaceful retreat within easy walking distance of Chestertown's bustling waterfront. The apartment has received excellent ratings for cleanliness, location, and overall experience, making it a great choice for travellers looking for a comfortable and convenient stay.
The apartment is spacious and comfortably accommodates up to eight guests, with three bedrooms and three bathrooms. Guests can enjoy a well-equipped kitchen, designated lounge areas with streaming TV, and a cosy gas fireplace for chilly evenings.

This three-bedroom apartment in Downtown Chestertown is just a short walk from the town's shops, cafes, and restaurants.
The apartment, spread over two floors, comfortably accommodates seven guests and features a fully equipped kitchen, two bathrooms, and free on-street parking.

This charming apartment is located just 500 metres from Washington College and a 1.5 kilometre walk from Chestertown's historic downtown, offering easy access to the town's attractions and amenities. The property has consistently received excellent ratings for its location, cleanliness and overall user experience.
The apartment is a three-bedroom, two-bathroom property that can accommodate up to six guests. It features a fully equipped kitchen, air conditioning, a garden, and parking, as well as access to a range of outdoor activities within a 20-kilometre drive.

This three-bedroom, three-bathroom apartment in Chestertown is situated within 0.32 kilometres of the town centre, offering easy access to shops, restaurants, and the farmers' market.
The self-catering property sleeps eight guests and boasts a spacious kitchen/family room, a private patio, and is close to Rolph's Wharf Marina, Cassinelli Winery and Vineyards, Crumpton Auction, and the Hazel Miner Monument.