Vacation rentals in Chestertown, MD

This dog-friendly house offers a walkable proximity to Historic Chestertown, with New Castle Airport located 45 miles away.
This 970 square foot accommodation features air conditioning, complimentary WiFi, and on-site parking, accommodating up to 11 guests with 2 bedrooms and 2 bathrooms, and includes a fully equipped kitchen with a dishwasher and an outdoor dining area.

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 studio apartment is located just two blocks from High Street in downtown Chestertown, near Evergrain Bakery, and about four blocks from the Chester River, making it a great base for exploring the town's shops, restaurants, and waterfront. The studio has received excellent ratings for location, cleanliness, and overall user experience.
The apartment features a comfortable bedroom with a queen-size bed and a private bathroom. It can comfortably accommodate two guests. The studio has a fully equipped kitchen with a refrigerator, freezer, microwave, and dishwasher, as well as a garden and access to a shared porch.

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.

This Chestertown colonial townhouse rental is located on a quiet block in the historic downtown, steps from the Chester River, farmers market, and restaurants.
The two-bedroom, one-bathroom dwelling offers a fully equipped kitchen, private patio, and accommodates up to four guests, perfect for exploring Chestertown's festivals and waterfront activities.

This Chestertown waterfront home, a six-bedroom, five-bathroom rental, is located on the Chester River, a four-block walk from Chestertown's historic district and its shops.
The 33x24-foot living/dining area, plus a ground floor great room with a pool table, accommodates up to 14 guests; amenities include two kitchens, a private pier, kayaks, and a paddleboard.

This newly painted Chestertown carriage house, located behind a Victorian row house, offers a short walk to Chestertown's downtown shops and historical sites.
The upstairs apartment features a modern kitchen, a tiled bathroom, and accommodates two guests with a private garden view, covered parking including EV charging, and easy access to the entire unit and a secure garage.

This charming two-bedroom house is located in the heart of Chestertown, just two blocks from Washington College and four blocks from the waterfront. It's close to shops, restaurants, and the farmer's market, making it an ideal spot for exploring the town. Guests have consistently rated this home excellent for its location, cleanliness, and overall experience.
The house offers a private and comfortable stay for up to four guests. You'll enjoy access to a fully equipped kitchen, a private garden, a fitness center, and other amenities perfect for a relaxing getaway.

This Chestertown apartment is located within walking distance of the town's charming downtown area, offering easy access to shops, restaurants, and attractions. The apartment has received excellent ratings for cleanliness, location, and user experience.
The apartment features a spacious living room and two dining areas. It is fully equipped with clean linens, towels, a well-stocked kitchen, laundry access, and free Wi-Fi.

This waterfront home in Chestertown is located just a 10-minute walk from the historic downtown, offering easy access to charming shops, restaurants, and art galleries. The property enjoys excellent user, location, and cleanliness ratings, making it a top choice for travelers. This spacious home features three bedrooms and two bathrooms, comfortably accommodating up to six guests. The house boasts a well-equipped kitchen, a large screened-in porch, a backyard with a fire pit, and access to a tidal beach, kayaks, paddleboards, and a canoe for exploring the river.

This newly updated one-bedroom, one-bathroom apartment in Chestertown is a short walk from the downtown area and waterfront, making it an ideal base for exploring the town. This pet-friendly rental offers internet, air conditioning, a full kitchen with a dishwasher, and a garden, accommodating up to two guests starting mid-April 2026.

This Chestertown apartment rental, located in the historic district, offers a riverfront location with easy walking access to shops and restaurants.
The third-floor unit features a king-size bed, one bedroom, one bathroom, a fully equipped kitchen, private rooftop deck with Chester River views, kayak/canoe access, and complimentary streaming services for up to two guests.