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

This charming apartment is situated in the heart of historic Chestertown, just a short walk from the town's shops, restaurants and Washington College. It has received excellent ratings for its location, cleanliness and overall user experience.
The apartment has two bedrooms and two bathrooms, comfortably accommodating up to four guests. It is well-equipped with modern amenities, including a fully fitted kitchen, high-speed internet, air conditioning, a private garden and parking.

This waterfront house is located just 1 kilometre from the historic downtown area of Chestertown, offering easy access to shops, restaurants, and attractions. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The spacious house has 3 bedrooms and 2 bathrooms, comfortably accommodating up to 6 guests. Enjoy a range of amenities including a fully equipped kitchen, a private garden, a fitness centre, and direct access to the river for kayaking, paddleboarding, and canoeing.

This newly furnished one-bedroom flat in Chestertown, available from mid-April 2026, offers guests the chance to be among its first visitors following its conversion to short-term rental, with specific district and landmark proximity to be confirmed post-renovation. This pet-friendly apartment includes a kitchen with fridge, freezer, microwave, and dishwasher, air conditioning, a garden, and accommodates up to two guests, providing a fresh base for exploring the town.

This Chestertown apartment is centrally located in the downtown area, a short walk (0.8 km) from the Chester River and Washington College.
The two-bedroom, one-and-a-half-bathroom property sleeps four, boasting an updated kitchen with fridge, microwave, and dishwasher, air conditioning, parking, and is within easy reach of the Arts & Entertainment District and numerous festivals.

This studio apartment is located just 0.8 kilometres from High Street in Chestertown, Maryland, a short walk from shops, restaurants, and the Chester River. It has consistently received excellent ratings for location, cleanliness, and overall experience.
The self-catering apartment is ideal for a couple or solo traveller, featuring a bedroom with a queen-size bed and a private bathroom. Amenities include a fully equipped kitchen, access to streaming services, and a shared garden, making it a comfortable and convenient base for exploring the area.

This waterfront house is located just 400 metres from the historic downtown area of Chestertown, offering easy access to restaurants, shops, and attractions. The property boasts excellent user ratings, making it a popular choice for travellers.
The house is ideal for large groups, comfortably accommodating up to 14 guests. It features a spacious living area, a ground floor games room, and a fully equipped kitchen, along with a screened-in porch, kayaks, a paddleboard, and a pool table for entertainment.

This Chestertown apartment, centrally located within a 0.6km radius of River Arts Chestertown, the Garfield Center for the Arts, and the Historical Society of Kent County, Maryland, offers easy walking access to cultural attractions and Wilmer Park.
The 48 square metre flat features one bedroom, one bathroom, sleeps two guests, and includes a kitchenette with fridge, freezer, and microwave, plus a private fenced yard, balcony, and free Wi-Fi.

This Chestertown house, a five-year-old rancher, is conveniently located within walking distance of Washington College and Chestertown's town centre.
Sleeping up to 10 guests, this three-bedroom, two-bathroom property boasts a fully equipped kitchen with dishwasher, a garden with Weber grill and Solo Stove fire pit, four televisions, central air conditioning and heating, and ample parking; numerous consumables are provided.

This charming flat in Chestertown is ideally located within walking distance of the town's main attractions, offering easy access to shops, restaurants, and historical landmarks. The apartment has received excellent ratings for cleanliness, location, and overall user experience.
The flat is spacious and well-equipped, featuring a large living room, two dining areas, and a laundry room. Amenities include a fully equipped kitchen, air conditioning, a garden, and parking.

This Chestertown residence is a 14-minute walk from the Kent County Historical Society and a 15-minute walk to Wilmer Park, offering convenient access to local attractions.
This 90 square metre holiday home accommodates up to six guests, featuring two bedrooms, two bathrooms, a private garden, a terrace, barbecue facilities, and on-site parking.

This charming apartment is situated in the heart of Chestertown's historic district, just a short walk from the town's bustling restaurants, shops, and the picturesque Chester River waterfront. It has received excellent ratings for its location, cleanliness, and overall experience.
The apartment has three bedrooms and two bathrooms, comfortably accommodating up to five guests. It features a well-equipped kitchen with modern appliances, a spacious living area, and a private outdoor space with a covered porch and a pergola, perfect for relaxing and enjoying the beautiful surroundings.