Holiday Rentals in Chestertown, MD

This property is located in Chestertown, within 500 meters of its dining, shopping, and waterfront attractions, and close to the Saturday Farmers Market.
This three-bedroom, one-bathroom flat accommodates up to six guests and features a well-equipped kitchen, air conditioning, a garden, and a screened-in porch.

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 luxurious waterfront property, situated 1.6km from Chestertown's town centre and adjacent to the Chester River Yacht & Country Club, offers stunning water and golf course views.
The 167 square metre home boasts three bedrooms, three bathrooms, and sleeps eight guests, featuring a fully equipped kitchen, air conditioning, and access to a garden; wildlife viewing opportunities abound.

This Chestertown holiday home is situated within a 2.4km walk of Kingstown Park, the Historical Society of Kent County Maryland, and the Garfield Center for the Arts, with Washington College and River Arts Chestertown also within 1.6km.
The 134 square metre property boasts three bedrooms, three bathrooms, sleeps six guests, and includes a fully equipped kitchen, free Wi-Fi, a private patio, and is within walking distance of several attractions.

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 apartment is located just a block from the waterfront in Kingstown, within walking distance of shops, galleries, and restaurants, offering a peaceful retreat in a quiet area of Chestertown. It has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience.
This home, a charmingly renovated "American Four Square" style house, can accommodate up to seven guests and offers full use of the first and second floors. The property features a fully equipped kitchen, comfortable bedrooms with high-quality mattresses, air conditioning, a garden, parking, and internet access.

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 magnificent 6-bedroom manor house, situated on a 325-acre farm six miles (approximately 9.7km) outside Chestertown, Maryland, on Morgan Creek, offers a tranquil escape near Kingstown.
The 557-square-metre property boasts a private pool, spa, and extensive grounds including walking trails, a vineyard, and shoreline access, alongside concierge services such as a private chef and daily housekeeping.

This waterfront property is situated just 14.5 kilometres from Washington College, River Arts Chestertown, and Rolphs Wharf Marina, offering easy access to local attractions and a peaceful setting. The home has received excellent ratings for cleanliness, location, and user experience, making it a popular choice for travellers.
The house spans 139 square metres and comfortably accommodates up to six guests. It offers a range of amenities, including a fully equipped kitchen, air conditioning, a terrace, a garden, a spa, a bar, parking, and free breakfast, ensuring a comfortable and enjoyable stay.

This 3-bedroom flat is located in a quiet Kingstown neighbourhood, offering excellent birdwatching and a short 3-kilometre drive to the central business district.
Guests can enjoy a wood-burning fireplace, a private garden, and keyless entry, with amenities including WiFi, air conditioning, and on-site laundry facilities for up to 4 people.

This charming 19th-century house is located in Chestertown's historic district, just 0.3 kilometres from Washington College and the waterfront. The accommodation consistently receives excellent ratings for its cleanliness, location, and overall guest experience.
The property offers five bedrooms, sleeping up to 10 guests, and features a spacious garden and a fenced yard. Guests can enjoy modern conveniences like fast internet, a fully equipped kitchen, and a comfortable living space, as well as access to the expansive gardens located just outside the back gate.