Hotels in Chestertown, MD

This Fairlee holiday home is situated in a wooded neighbourhood near Chestertown, Maryland, offering easy access to the Chesapeake Bay and its wildlife, approximately 1.6km from the historic Chestertown town centre.
Sleeping seven guests, the three-bedroom property boasts two bathrooms, a fully equipped kitchen with dishwasher, air conditioning, a spacious dining room, family room with sectional sofa, outdoor spaces with fire pit and picnic table, plus unique interior design features including a 'McCloskey Room'.

This two-bedroom flat is located in historic Chestertown, a mere 200 metres from the High Street Wharf.
This pet-friendly accommodation offers space for five guests, with air conditioning, internet, and parking, and is ideal for exploring Chestertown's festivals and river attractions.

This five-bedroom guesthouse in Worton, a short drive from Betterton Beach, offers convenient access to the Kent Museum and Historical Society of Kent County Maryland and Hidden Lake.
The 139 square metre (approximately 1496 square feet) property sleeps ten guests and includes a full kitchen, microwave, fridge, two bathrooms, air conditioning, parking, and Wi-Fi; hunting and birdwatching opportunities are also nearby.

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.