Holiday Rentals in Chestertown, MD

This five-bedroom apartment is situated in a secluded location, just a short drive from the heart of Kingstown, offering peace and quiet in a tranquil setting. It has consistently received excellent ratings for its cleanliness, location, and overall user experience.
The spacious property can accommodate up to 16 guests, providing ample room for families or large groups. Guests can enjoy a range of amenities, including a private saltwater pool, a hot tub, a fully equipped kitchen, and a garden with a fire pit and outdoor seating, perfect for relaxing and enjoying the beautiful surroundings.

This 19th-century retreat, located in Still Pond, offers an apartment just a 15-minute drive from historic Chestertown and is conveniently situated near Rock Hall, Betterton Beach, Georgetown, and local vineyards.
This 42 square meter apartment accommodates up to three guests, featuring a private living room with a pullout sofa, a queen bedroom with a Purple mattress, an en-suite bathroom with a multi-head shower, and an in-suite kitchenette, with shared access to a wraparound porch and farmhouse deck ideal for boaters.

This charming Victorian house is situated in Chestertown, just a short walk from the historic district and waterfront, providing easy access to the town's attractions. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
This spacious home offers four bedrooms and two and a half bathrooms, making it ideal for families or groups. Guests can enjoy a gourmet kitchen, a private garden, and a garage with electric vehicle charging, perfect for exploring the area.

This one-bedroom flat is located in Worton, a peaceful rural area just 13 kilometres from Betterton Beach and 28 kilometres from Rolphs Wharf Marina. It has received excellent user ratings, making it a popular choice for travellers.
The flat can accommodate up to four guests and features a fully equipped kitchen, a comfortable living area, and a bathroom with a hairdryer and towels. Guests can enjoy access to a fire pit, barbecue facilities, free Wi-Fi, and a smart TV, as well as nearby laundry facilities and opportunities for nature walks and birdwatching.

This three-bedroom apartment is located on the third floor of Portside Manor, offering a peaceful retreat within easy walking distance of Chestertown's bustling waterfront. The apartment has received excellent ratings for cleanliness, location, and overall experience, making it a great choice for travellers looking for a comfortable and convenient stay.
The apartment is spacious and comfortably accommodates up to eight guests, with three bedrooms and three bathrooms. Guests can enjoy a well-equipped kitchen, designated lounge areas with streaming TV, and a cosy gas fireplace for chilly evenings.

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 waterfront home is situated just a short distance from Chestertown’s historic district, offering easy access to cultural attractions and the beautiful Chesapeake Bay. The property has received excellent reviews from previous guests, highlighting its tranquil location and comfortable amenities.
This spacious three-bedroom property can comfortably accommodate up to 10 guests. Amenities include a fully equipped kitchen, a private dock, kayaks, bikes, a hot tub, and a tennis court, providing everything you need for a relaxing 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 Victorian home is situated in Chestertown's Historic District, just a short walk from Washington College, restaurants, shops, and the Chester River waterfront. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The apartment is a spacious property that can comfortably accommodate up to 12 guests. The recently renovated home offers a stylish beachy-chic décor, a fully equipped kitchen with modern appliances, and a charming outdoor space with a front porch, rear deck, and a fully fenced backyard.

This charming 3-bedroom apartment is situated in the historic district of Chestertown, just a short walk from the bustling High Street and two blocks from the picturesque Chester River. The property has received excellent ratings for location, cleanliness, and overall user experience.
The apartment offers ample space for families or groups of friends, with three bathrooms and a capacity of six guests. Enjoy modern amenities such as a fully equipped kitchen, a washer and dryer, a gas fireplace, and a private garden with a screened porch and a brick terrace, perfect for relaxing evenings.

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 private waterfront cottage on Langford Creek is a short drive from Chestertown's downtown amenities, including restaurants, shops, and its farmers market.
This 3-bedroom, 2-bathroom dwelling accommodates up to 6 guests and features a well-equipped kitchen, air conditioning, a Jacuzzi, garden, parking, a private deck with a hot tub, an outdoor shower, and a private pier with a boat slip.