Chestertown, MD Motels: no available offers. Here are other great options for your stay!

Pet-friendly Home On Chester River W/ Dock!
house, Kingstown
This four-bedroom house is situated in a peaceful residential area, approximately 77 kilometres from New Castle Airport. The property offers a spacious 300 square metre layout, accommodating up to 27 guests and featuring amenities such as a swimming pool, garden, and private parking.

Loft At Fountain Park - Prime Downtown Location
apartment, Chestertown
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 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.

Walk To Historic Chestertown: Dog-friendly Retreat
cottage, Chestertown
This cottage is located in Chestertown, within 1.5 kilometres of Washington College, River Arts Chestertown, Garfield Center for the Arts, Sumner Hall, and the Chestertown Historic District.
This property offers a well-equipped kitchen with a microwave and dishwasher, air conditioning, and on-site barbecue grills, with WiFi available in public areas.
This property offers a well-equipped kitchen with a microwave and dishwasher, air conditioning, and on-site barbecue grills, with WiFi available in public areas.

Owl Cottage - Cozy, Private & Walkable To Town
house, Chestertown
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.
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.
