350-acre Waterfront Estate On The Chester River
apartment, Kingstown
This waterfront estate in Kingstown offers direct access to the Chester River and is located just minutes from the historic district of Chestertown, Maryland.
This apartment accommodates up to 8 guests and features a kitchen with a fridge, freezer, microwave, and dishwasher, air conditioning, a swimming pool, garden, and parking.
This apartment accommodates up to 8 guests and features a kitchen with a fridge, freezer, microwave, and dishwasher, air conditioning, a swimming pool, garden, and parking.
High Tide Haven Suite
apartment, Betterton
This Still Pond suite is located a 15-minute drive from historic Chestertown and offers proximity to Betterton Beach and the Betterton Historic District.
This 450-square-foot apartment accommodates up to three guests with a queen bedroom featuring a Purple mattress, a living room with a pullout couch, an en-suite bathroom with a multi-head shower, and a kitchenette, plus access to shared farmhouse grounds including a porch, deck, and grill.
This 450-square-foot apartment accommodates up to three guests with a queen bedroom featuring a Purple mattress, a living room with a pullout couch, an en-suite bathroom with a multi-head shower, and a kitchenette, plus access to shared farmhouse grounds including a porch, deck, and grill.
The Patriot House-chestertown, Md
apartment, Chestertown
This Chestertown apartment is located within walking distance of the town's charming downtown area, offering easy access to shops, restaurants, and attractions. The apartment has received excellent ratings for cleanliness, location, and user experience.
The apartment features a spacious living room and two dining areas. It is fully equipped with clean linens, towels, a well-stocked kitchen, laundry access, and free Wi-Fi.
The apartment features a spacious living room and two dining areas. It is fully equipped with clean linens, towels, a well-stocked kitchen, laundry access, and free Wi-Fi.
Pool + Hot Tub + Pickleball | Waterfront
apartment, Kingstown
This Kingstown waterfront home sits on a secluded 5-acre property, just a short distance from the town's main attractions, offering privacy and stunning river views. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. This spacious home features five bedrooms and three bathrooms, accommodating up to 16 guests. The home offers a fully equipped kitchen, a saltwater pool, a hot tub, a fire pit, and access to kayaking and paddleboarding on the river, providing ample opportunities for relaxation and entertainment.
House On The Hill - Historic Private Second Floor
house, Chestertown
This charming bed and breakfast is located in historic Chestertown, just a short walk from the town center and a quick drive from the Chester River. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The second floor is dedicated to guests, offering two bedrooms, a private bathroom, and a sitting area, comfortably accommodating up to four guests. Guests can enjoy the outdoor space with chairs and a fire pit, relax in the sitting area with a mini fridge and Keurig coffee maker, and possibly even meet Andy the orange cat.
The second floor is dedicated to guests, offering two bedrooms, a private bathroom, and a sitting area, comfortably accommodating up to four guests. Guests can enjoy the outdoor space with chairs and a fire pit, relax in the sitting area with a mini fridge and Keurig coffee maker, and possibly even meet Andy the orange cat.
Riverfront Retreat
apartment, Chestertown
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.
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.
Rovers Retreat - Chestertown Charmer - N Kent St
apartment, Chestertown
This 1907 house, a 3-bedroom, 2-bathroom apartment for 6 guests, is located in Chestertown's historic district, 1 block from Washington College and 4 blocks from downtown Chestertown's shops and Arts & Entertainment district.
This ground-floor unit offers an en suite bedroom, in-unit laundry, a full kitchen with a dishwasher, a porch, a brick patio, and a ramp for the back entrance, with driveway parking for a small car and ample on-street parking available.
This ground-floor unit offers an en suite bedroom, in-unit laundry, a full kitchen with a dishwasher, a porch, a brick patio, and a ramp for the back entrance, with driveway parking for a small car and ample on-street parking available.
Harbor View Haven | Waterfront W/ Hot Tub + Dock!
apartment, Kingstown
This waterfront vacation home, located in the serene countryside of Chestertown, Maryland, offers easy access to local attractions such as Wilmer Park, the Historic District, and Washington College.
This four-bedroom, two-bathroom rental boasts a fully equipped kitchen with a Jura espresso machine, a private dock with kayaks, a hot tub, and accommodates up to ten guests, providing ample space for relaxation and outdoor recreation.
This four-bedroom, two-bathroom rental boasts a fully equipped kitchen with a Jura espresso machine, a private dock with kayaks, a hot tub, and accommodates up to ten guests, providing ample space for relaxation and outdoor recreation.
Cozy Cape Cod In Worton Md
apartment, Butlertown
This 3-bedroom, 3-bathroom Butlertown apartment rental is located in a quiet neighborhood, close to local restaurants and family-friendly attractions, though precise distances are unspecified.
The 3-bedroom home offers a large backyard, fridge, freezer, microwave, dishwasher, air conditioning, parking, and accommodates up to 7 guests, perfect for families or groups exploring Butlertown.
The 3-bedroom home offers a large backyard, fridge, freezer, microwave, dishwasher, air conditioning, parking, and accommodates up to 7 guests, perfect for families or groups exploring Butlertown.
In Town Chestertown Rancher (1 Block To College)
apartment, Chestertown
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.
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.
Historic Chestertown
apartment, Chestertown
This charming 3-bedroom apartment is conveniently located on the main street in Chestertown's Historic district, just a short walk from restaurants, shops, and the waterfront. The apartment consistently receives excellent ratings for its cleanliness, location, and overall experience.
The spacious home comfortably accommodates 5 guests and features an open floor plan kitchen and family room perfect for entertaining. Guests can enjoy the luxurious master suite, gourmet kitchen, outdoor living space, and detached garage with additional storage.
The spacious home comfortably accommodates 5 guests and features an open floor plan kitchen and family room perfect for entertaining. Guests can enjoy the luxurious master suite, gourmet kitchen, outdoor living space, and detached garage with additional storage.
Holly Pointe Estate, Sleeps 25+ Pool, Pickle Ball
apartment, Butlertown
This expansive 90-acre luxury estate in Worton offers stunning bay views and is a short drive from the Betterton Historic District and the Chesapeake Bay.
This residence accommodates up to 25 guests with 8+ bedrooms, featuring resort-style amenities including a swimming pool, pickleball court, and a well-equipped kitchen with two islands, two sinks, two dishwashers, and three refrigerators.
This residence accommodates up to 25 guests with 8+ bedrooms, featuring resort-style amenities including a swimming pool, pickleball court, and a well-equipped kitchen with two islands, two sinks, two dishwashers, and three refrigerators.
