Motels in Chestertown, MD

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.

This charming house is situated in the heart of Chestertown, just 0.4 kilometres from Washington College and 0.6 kilometres from the waterfront, offering easy access to the town's attractions. The property consistently receives excellent ratings for its location, cleanliness, and overall experience.
The house provides guests with access to the entire property, comfortably accommodating up to four guests. This spacious home features a fully equipped kitchen, a private garden, a fitness centre, and parking, ensuring a comfortable and enjoyable stay.

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 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.