Vacation rentals in Chestertown, MD

This charming two-bedroom house is located in the heart of Chestertown, just two blocks from Washington College and four blocks from the waterfront. It's close to shops, restaurants, and the farmer's market, making it an ideal spot for exploring the town. Guests have consistently rated this home excellent for its location, cleanliness, and overall experience.
The house offers a private and comfortable stay for up to four guests. You'll enjoy access to a fully equipped kitchen, a private garden, a fitness center, and other amenities perfect for a relaxing getaway.

This Chestertown house rental is conveniently located within walking distance of Washington College and Chestertown's downtown, offering easy access to shops, restaurants, and historical sites.
The three-bedroom, two-bathroom home sleeps up to ten guests and features a fully equipped kitchen with a dishwasher, a Weber grill, a Solo Stove fire pit, four TVs, central air conditioning, and ample parking.

This Chestertown colonial townhouse rental is located on a quiet block in the historic downtown, steps from the Chester River, farmers market, and restaurants.
The two-bedroom, one-bathroom dwelling offers a fully equipped kitchen, private patio, and accommodates up to four guests, perfect for exploring Chestertown's festivals and waterfront activities.

This renovated duplex offers a prime downtown Chestertown location, just steps from dining, shopping, and waterfront views.
This 950 sq ft home accommodates up to 4 guests with 2 bedrooms, 1 bathroom, a fully equipped kitchen, air conditioning, and a garden, featuring a unique 'Pole Pole' philosophy for relaxation and grip bars for staircase assistance.

Owl Cottage is a renovated carriage house located in the heart of Chestertown, just a short walk from the historic district and waterfront. The charming town offers a mix of history, art, and local shops and restaurants.
Owl Cottage is a cozy one-bedroom house that can accommodate up to four guests. It includes a fully equipped kitchen, a bathroom with a shower, and a private patio with access to over two acres of gardens.

This dog-friendly house offers a walkable proximity to Historic Chestertown, with New Castle Airport located 45 miles away.
This 970 square foot accommodation features air conditioning, complimentary WiFi, and on-site parking, accommodating up to 11 guests with 2 bedrooms and 2 bathrooms, and includes a fully equipped kitchen with a dishwasher and an outdoor dining area.

This Chestertown vacation home is located directly on the waterfront, just a four-block walk from the historic downtown area, offering easy access to charming shops, restaurants, and museums. The property has received excellent user ratings, making it a popular choice for travelers.
This spacious home has six bedrooms and seven bathrooms, comfortably accommodating up to 14 guests. The property features a private pier for kayaking, paddleboarding, and swimming, a pool table, a 75-inch television, a fully equipped kitchen, and a screened-in porch with seating for eight.

This 2-bedroom, 2-bathroom apartment in Chestertown is located within a 15-minute walk of the Kent County Historical Society and Wilmer Park, and a short distance to the Garfield Center for the Arts at the Prince Theater.
This 970 sq ft vacation home accommodates up to 6 guests and features a private garden, terrace, barbecue, air conditioning, Wi-Fi, a full kitchen, and on-site parking.

This Chestertown apartment rental, located in the historic district, offers a riverfront location with easy walking access to shops and restaurants.
The third-floor unit features a king-size bed, one bedroom, one bathroom, a fully equipped kitchen, private rooftop deck with Chester River views, kayak/canoe access, and complimentary streaming services for up to two guests.

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 studio apartment is located just two blocks from High Street in downtown Chestertown, near Evergrain Bakery, and about four blocks from the Chester River, making it a great base for exploring the town's shops, restaurants, and waterfront. The studio has received excellent ratings for location, cleanliness, and overall user experience.
The apartment features a comfortable bedroom with a queen-size bed and a private bathroom. It can comfortably accommodate two guests. The studio has a fully equipped kitchen with a refrigerator, freezer, microwave, and dishwasher, as well as a garden and access to a shared porch.

This Chestertown waterfront home, a six-bedroom, five-bathroom rental, is located on the Chester River, a four-block walk from Chestertown's historic district and its shops.
The 33x24-foot living/dining area, plus a ground floor great room with a pool table, accommodates up to 14 guests; amenities include two kitchens, a private pier, kayaks, and a paddleboard.