Chestertown, MD 21620, USA apartments for rent

My place is located in a quaint neighborhood close to downtown Chestertown; 1 mile walk. This home has a large screened porch & inviting outside patio. Cruise the Chester River with the canoe or two paddle boards provided. Feel free to bring your boa...

Adorable two bedroom home on a gorgeous lot in a coveted corner of Downtown Chestertown! Just one block from the College and a short walk to the heart of town and the waterfront. House is Fully furnished and move in ready! Rent ($1879/mo) incl...

Down a half mile lane, surrounded by woods and farm land. This property is located between Chestertown and Rock Hall, Maryland. Just a half mile away from the Chesapeake Bay, this cottage is a wonderful vacation get away. The great room has a queen s...

“Old Bridge” is a 100-year-old house in a quiet Kingstown section of Chestertown. The house is an "American Four Square" style home recently renovated from top to bottom. Walk a block to the waterfront or visit the shops, galleries and restaurants cl...

Chester River Dreams, offers spectacular views of the Chester River from the Family room, Kitchen, & Dining room, Deck, not to mention from the 'L' head on the dock. All the other rooms enjoy a view of a large pond where you can watch Osprey, Eagles ...

Welcome to Riverfront Retreat, a beautiful and spacious home where your family will be able to relax and enjoy the best of the Eastern Shore. With two main floor bedrooms, including a master suite accompanied with sitting room with full river views. ...

The River Lodge sits on the scenic Chester River located 5 miles outside of Chestertown. It's the perfect little get away. You'll experience beautiful sunsets and tranquil nights. During the day sit in a chair on your small private beach and bask...

Step into modern comfort and style with this recently built 2023 home, offering 4 spacious bedrooms and 2 bathrooms. Designed with an open-concept layout, the home is filled with natural light and features a sleek, contemporary kitchen complete with ...

The privacy of a waterfront home welcomes you to pause and enjoy the beauty of the Chester River. Water views from every window connects you to the flowing water and the expansive outdoors. The southern exposure welcomes spectacular sunrises and suns...

Escape to tranquility at Mill Creek House, a contemporary waterfront sanctuary just 15 mins from Chestertown. Enjoy sunset views from the private dock, watch wildlife, and explore the creek with kayaks. Modern amenities like central AC, WiFi, and a g...

Enjoy historic ambiance with every modern convenience, including a first floor bedroom with private bath. Our house is in the historic district of Chestertown, and a two block walk from both Washington College and the Chestertown waterfront. It f...

Welcome to this freshly renovated, waterfront home on the Chester River. Gorgeous sunsets, picturesque views of the River, endless wildlife… these are just some of our favorite things about this property. Whether you are boating, fishing or just rela...

Welcome to 108Annex, your ideal Chesapeake Bay retreat! Nestled in historic downtown Chestertown, our one-bedroom guesthouse is the perfect place for couples or solo travelers to enjoy a long relaxing weekend. Just steps away from downtown restaurant...

Newly renovated apartment in downtown Chestertown. Directly across the street from Evergrain Bakery. In the center of all Chestertown has to offer. This apartment span the entire front of a recently restored building, built in 1877. Open living room/...

Brittland Manor was built in 1938 and sits on 530 riverside acres. When you drive up the long curved lane you are surrounded by fields, woods, a pond, and wild life. Enjoy the river view on a large brick patio, play a yard game in the garden with the...

***All New Mattresses installed March 2022*** Thornton Estate, established in 1664, is a quintessential Eastern Shore estate. The magnificent manor house anchors the 325 acre preserved farm outside of Chestertown Maryland. Lord Baltimo...

Modern cottage on tranquil large grounds on 20 acres with a pond on one end and a half mile wide creek 800 feet away on the other with a 100 foot dock. Inside a larger historic 18th century farm with original house and buildings. Expansive views. See...

Welcome to our charming Chestertown Home! This beautiful house offers a comfortable and inviting space for your stay. With two full bedrooms and bathrooms on the second floor and a cozy third-floor retreat with two twin beds, there is plenty of room ...

Accommodations: Manor House - Five Bedrooms (including one Private Suite), three and one-half Baths, Sitting Room, Den, Formal Dining Room, Kitchen and Sun Room (Sleeps 15).In 1659, a Mariner by the name of Peter Bovery was granted acreage for wh...

Breathe in the fresh waterfront air and enjoy a laid-back stay on the eastern shore of Maryland when you book this home in Chestertown! Highlighted by 5 bedrooms, 2.5 bathrooms, and a wraparound porch, this vacation rental offers a comfortable stay f...

Welcome to Eagle Point Farm located on Maryland's beautiful Eastern Shore, a 90 minute drive from Washington DC, Philadelphia or Baltimore. Experience the beauty of the Chester River from this secluded farm located minutes from historic Chestertown, ...

Escape to a secluded, romantic studio getaway in the middle of Chestertown. Private parking, and over an acre of gardens to call your own. Totally private with views of nature all around, this is the perfect place to relax in front of the fireplace. ...