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 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 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 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 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 3-bedroom flat is located in a peaceful residential area of Chestertown, offering convenient access to local shops and dining within 1 kilometre.
This pet-friendly accommodation sleeps up to six guests and features a private entrance, a walk-in bathroom, a kitchenette with a microwave and mini-fridge, and a gas fireplace.

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 guesthouse is located in historic Chestertown, just a short walk from the town centre and a 3-kilometre drive from the waterfront. It has consistently received excellent ratings for its location, cleanliness, and overall guest experience.
The property offers a private second-floor suite with two bedrooms, a bathroom, and a sitting area, accommodating up to four guests. Guests can enjoy a garden with chairs and a fire pit, a mini-fridge, a coffee maker, and local recommendations from the friendly hosts.

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.

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.