$10,800
Available: Right Now
Listed: 04/06/2024
Chestertown, MD, 21620
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 ...
$3,300
Available: Right Now
Listed: 04/06/2024
Chestertown, MD, 21620
One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everything our private residence has to offer: private inground pool, seasonal hot tub, lush grounds and outdoor seating. The space is w...
$75,600
Available: Right Now
Listed: 05/06/2024
Chestertown, MD, 21620
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. You end at a circle drive in front of the Georgian style mansion. It's hilltop setti...
$19,020
Available: Right Now
Listed: 05/06/2024
Chestertown, MD, 21620
This private waterfront river home in beautiful historic Chestertown has its own private pier and pool - all on a quiet cul de sac. Enjoy the view from the river porch of the Eastern Shore sunset over glassy water, pick some Maryland Blue Crabs caugh...
$2,500
Available: 17/06/2024
Listed: 07/06/2024
413 Riverview Road
This spacious beautiful home has so much to offer. In addition to it's 4 car garage, you have a large deck off from the back of the house which is enclosed in the back yard which is fenced in giving much privacy, Above this large garage are separate ...
$4,740
Available: Right Now
Listed: 05/06/2024
Chestertown, MD, 21620
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...
$34,740
Available: Right Now
Listed: 05/06/2024
Chestertown, MD, 21620
***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...
$16,080
Available: Right Now
Listed: 05/06/2024
Chestertown, MD, 21620
Breathe in the fresh waterfront air and enjoy a laid-back stay on the eastern shore of Maryland when you book this expansive home in Chestertown! Highlighted by 5 bedrooms, 3 bathrooms, and a wraparound porch, this vacation rental offers a comfortabl...
$4,290
Available: Right Now
Listed: 04/06/2024
Chestertown, MD, 21620
Quaint and charming, our home away from home in historic Chestertown features 2 bedrooms and 2.5 bathrooms and can accommodate up to 4 adults. Just a few blocks from the downtown shops and restaurants. Also walkable to Washington College.The spac...
$10,950
Available: Right Now
Listed: 05/06/2024
Chestertown, MD, 21620
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...
$13,500
Available: Right Now
Listed: 04/06/2024
Chestertown, MD, 21620
Escape to our multiple-acre private paradise where you can enjoy breathtaking sunsets, gaze at countless stars, admire the wildlife, and dip into the water via our 200+ foot private beach. It's an ideal destination that you can enjoy for hours on end...
$7,050
Available: Right Now
Listed: 04/06/2024
Chestertown, MD, 21620
Our darling, historic cottage, recently featured on Chestertown's Historic House Tour, is comfortable, pet-friendly and contemporary (on the inside!). It's a superb central-to-everything location, and one of the few perfectly pet-friendly rentals...
$8,250
Available: Right Now
Listed: 05/06/2024
Chestertown, MD, 21620
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...
$5,160
Available: Right Now
Listed: 05/06/2024
Chestertown, MD, 21620
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...
$18,510
Available: Right Now
Listed: 04/06/2024
Chestertown, MD, 21620
Goose Landing is a 3+ acre 4 bedroom 2.5 bathroom secluded waterfront home nestled on Fairlee Creek that boasts 350 feet of waterfront with panoramic views from almost every room, and a large dock for relaxing, birdwatching , and fishing. Fairlee Cre...
$15,000
Available: Right Now
Listed: 05/06/2024
Chestertown, MD, 21620
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...
$8,430
Available: Right Now
Listed: 05/06/2024
Chestertown, MD, 21620
Beautiful1900 built home that has all of its historic charm while having updated amenities. Enjoy everything historic Chestertown has to offer as the house is walking distance to the shops, restaurants, Chester River Waterfront, and year round Saturd...
$16,500
Available: Right Now
Listed: 04/06/2024
Chestertown, MD, 21620
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...
$23,250
Available: Right Now
Listed: 04/06/2024
Chestertown, MD, 21620
Private, one-of-a-kind waterfront home on the Chester River minutes from historic Chestertown. Drive through a gated entry past your private pool and extensive landscaping to a spectacular vista sweeping the riverfront. Bring your own boat or simply ...
$18,000
Available: Right Now
Listed: 05/06/2024
Chestertown, MD, 21620
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...
$20,250
Available: Right Now
Listed: 04/06/2024
Chestertown, MD, 21620
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...
$19,290
Available: Right Now
Listed: 04/06/2024
Chestertown, MD, 21620
A delightful hideaway! Completely remodeled Victorian row house, with four bedrooms, two and a half-bathrooms, a gourmet kitchen, two porches, antiques, rugs, and several writing spaces. Dual zone HVAC, washer & dryer, high-speed internet. Off-street...