Holiday Rentals in Chestertown, MD

This Chestertown property, a two-bedroom, two-bathroom flat, is located near historic streets and the Chester River, offering convenient access to downtown attractions, including art galleries, and Wilmer Park, all within 1 kilometre of the accommodation.
This pet-friendly apartment accommodates up to six guests and features a well-equipped kitchen with a Cuisinart dual coffee maker, air conditioning, a fireplace, a fenced garden with a furnished deck, and off-street parking.

Owl Cottage is a renovated carriage house located in the centre of Chestertown, just a short walk from the historic district and waterfront. This charming cottage offers a unique blend of historic charm and modern convenience.
The property has a unique layout with a ground floor bedroom, a second floor living/kitchen area with a bathroom, and a third floor loft with a queen-sized bed. The cottage comfortably sleeps up to four guests and includes a private garden, patio, and pet-friendly amenities.

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.

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 apartment is situated in the heart of Chestertown, just a short walk from Washington College, the Chester River and the town's historic district, with easy access to shops and restaurants on High Street. The apartment has received excellent ratings for location, cleanliness and overall experience.
This spacious property spans two levels and offers four bedrooms, comfortably accommodating up to eight guests. The apartment boasts a fully equipped kitchen, air conditioning, a garden and parking, ensuring a comfortable and enjoyable stay.

This Chestertown townhouse, located on a quiet street in the historic downtown area, is steps from the farmers' market, Chester River, and numerous restaurants.
The two-bedroom, one-bathroom property sleeps four guests and features a fully equipped kitchen with dishwasher, a private patio for al fresco dining, and free on-site parking; enjoy easy access to local festivals and waterfront walks.

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 six-bedroom, five-bathroom waterfront property in Chestertown is situated on the Chester River, a short 0.4-kilometre walk from the historic town centre.
The 14-guest dwelling boasts two kitchens, a ground-floor great room with a pool table and 75-inch television, extensive outdoor space including a private pier with kayaks and paddleboard access, and fresh 2021 updates.

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 renovated duplex offers a prime downtown Chestertown location, mere steps from dining, shopping, and waterfront views.
This 93-square-meter dwelling sleeps four, featuring two bedrooms, one bathroom, and a fully equipped kitchen, with grip bars on the staircase for added accessibility.

This Chestertown apartment, located in the historic district, offers a riverfront position on the Chester River, within easy walking distance of the town's attractions.
The third-floor flat boasts a king-size bed, a well-equipped kitchen including a four-burner range and oven, a private rooftop deck with Chester River views, and complimentary access to kayaks/canoes, accommodating up to two guests.

This Chestertown carriage house, situated at the rear of a Victorian property, offers a peaceful retreat a short walk from the town centre.
The property comprises a fully equipped kitchen, modern bathroom, and private garden with covered parking including EV charging; sleeping two guests, it provides all linens and towels.