Best apartment offers in Chestertown, MD

Stepne Manor is a five-bedroom house situated in the historic district of Chestertown, Maryland, a short walk from Fountain Park, the Chestertown Marina, and Wilmer Park on the Chester River. This property has received excellent ratings for its location, cleanliness, and overall user experience.
The house comfortably accommodates 15 guests and features a private suite with a Jacuzzi tub. Guests can enjoy a range of amenities including a garden, a terrace, and a spa, as well as modern comforts like air conditioning, satellite TV, and a fully equipped kitchen.

This waterfront estate in historic Chestertown, Maryland, offers direct access to the Chester River and is just minutes from the town's historic district, providing a secluded retreat with extensive natural beauty.
This spacious apartment accommodates up to eight guests, featuring a private garden, swimming pool, and parking, with air conditioning, internet, and a fully equipped kitchen including a fridge, freezer, microwave, and dishwasher, ideal for family holidays or group getaways.

This riverfront property is situated just three miles from the centre of Chestertown, a charming town with a rich history and a bustling waterfront, and is also within easy reach of other popular destinations such as Rock Hall, Annapolis and St. Michaels. The property has received excellent ratings for its location, cleanliness and overall experience.
The house has three bedrooms and can accommodate up to ten guests, making it ideal for families or groups of friends. Guests can enjoy a range of amenities including a fully equipped kitchen, a private dock and boat lift, a spacious terrace, a garden, a fitness centre and air conditioning.

Harbor View Haven is a waterfront property situated in Chestertown, Maryland, just a short drive from the historic town centre.
This spacious house boasts three bedrooms and two bathrooms, sleeping up to ten guests, and features a private dock, a hot tub, a fully equipped kitchen, and a game room with a ping pong table.

This Chestertown waterfront house, a 1.6km stroll from the Historic District, offers direct access to the Chester River with a private boat dock.
Sleeping up to 14 guests, the spacious property boasts four bedrooms, four bathrooms, a sunroom, a games room, kayaks, canoes, two grills, and a private seasonal outdoor pool (15 May – 15 September).

This studio flat is a secluded retreat in Chestertown, offering over 0.4 hectares of private gardens and convenient access to local attractions.
This romantic hideaway accommodates two guests and features a king-size bed, a well-equipped kitchenette with a two-burner hot plate and microwave, a fireplace, and an in-unit washer and dryer, with pets welcome and private parking provided.

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 three-bedroom, three-bathroom apartment in Chestertown is situated within 0.32 kilometres of the town centre, offering easy access to shops, restaurants, and the farmers' market.
The self-catering property sleeps eight guests and boasts a spacious kitchen/family room, a private patio, and is close to Rolph's Wharf Marina, Cassinelli Winery and Vineyards, Crumpton Auction, and the Hazel Miner Monument.

This Chestertown townhouse, located on a quiet street in the historic downtown area, is steps from the farmers' market, Chester River, and numerous restaurants.
The two-bedroom, one-bathroom property sleeps four guests and features a fully equipped kitchen with dishwasher, a private patio for al fresco dining, and free on-site parking; enjoy easy access to local festivals and waterfront walks.

This studio apartment is located just 0.8 kilometres from High Street in Chestertown, Maryland, a short walk from shops, restaurants, and the Chester River. It has consistently received excellent ratings for location, cleanliness, and overall experience.
The self-catering apartment is ideal for a couple or solo traveller, featuring a bedroom with a queen-size bed and a private bathroom. Amenities include a fully equipped kitchen, access to streaming services, and a shared garden, making it a comfortable and convenient base for exploring the area.

This magnificent 6-bedroom manor house, situated on a 325-acre farm six miles (approximately 9.7km) outside Chestertown, Maryland, on Morgan Creek, offers a tranquil escape near Kingstown.
The 557-square-metre property boasts a private pool, spa, and extensive grounds including walking trails, a vineyard, and shoreline access, alongside concierge services such as a private chef and daily housekeeping.

This 3-bedroom flat is located in a quiet Kingstown neighbourhood, offering excellent birdwatching and a short 3-kilometre drive to the central business district.
Guests can enjoy a wood-burning fireplace, a private garden, and keyless entry, with amenities including WiFi, air conditioning, and on-site laundry facilities for up to 4 people.