Vacation rentals in Chestertown, MD

Stepne Manor is a renovated 17th-century manor house located in Chestertown, Maryland, within walking distance of Fountain Park and its colonial architecture and shops. The property has received excellent ratings for user experience, location, and cleanliness.
The house has five bedrooms and can accommodate up to 15 guests, making it ideal for large families or groups. Stepne Manor offers modern amenities like air conditioning, a fully equipped kitchen, a spa, and a private terrace with a garden, as well as access to nearby water activities like kayaking and jet skiing.

This historic Chestertown apartment offers riverside breezes and is located within walking distance of downtown Chestertown's art galleries and Wilmer Park.
This single-story dwelling accommodates up to six guests with two bedrooms, two bathrooms, a full kitchen, a furnished deck, a fenced backyard, and free WiFi, with eight steps for entry.

This Chestertown apartment rental boasts a prime location in the town center, offering easy walking access to shops, restaurants, and historical sites, with a direct view of Chestertown's festivals from its front.
The two-bedroom, one-bathroom unit features a spacious open-plan living/dining/kitchen area, a workspace, in-unit laundry, and off-street parking; it comfortably sleeps four guests.

This newly updated one-bedroom, one-bathroom apartment in Chestertown is a short walk from the downtown area and waterfront, making it an ideal base for exploring the town. This pet-friendly rental offers internet, air conditioning, a full kitchen with a dishwasher, and a garden, accommodating up to two guests starting mid-April 2026.