$10,950
Available: Right Now
Listed: 01/05/2024
Chestertown, MD, 21620
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 ...
$11,670
Available: Right Now
Listed: 01/05/2024
Chestertown, MD, 21620
Relax by the fire pit and watch the sun set over the pond and golf course! If you like birdwatching, we have amazing great blue herons, osprey, and the occasional bald eagle. Ride bikes into downtown Chestertown and enjoy the local restaurants, bars ...
$24,000
Available: Right Now
Listed: 01/05/2024
Chestertown, MD, 21620
BNB Breeze Presents: Langford Estates!Step into your very own, secluded 790-acre sanctuary! This 1864 home has been newly renovated to create the ultimate vacation destination for you and your loved ones. This home has everything from a luxurious...
$7,290
Available: Right Now
Listed: 04/05/2024
Chestertown, MD, 21620
Enjoy your stay in Chestertown in a waterfront home on a tidal creek that is only minutes from historic downtown and Washington College. There is plenty to do during your stay, whether you take the four provided kayaks out, play ping pong in the base...
$8,250
Available: Right Now
Listed: 30/04/2024
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...
$3,500
Available: 01/05/2024
Listed: 04/05/2024
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 ...
$7,920
Available: Right Now
Listed: 01/05/2024
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...
$2,940
Available: Right Now
Listed: 04/05/2024
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...
$2,000
Available: Right Now
Listed: 01/05/2024
139 Conley Drive, Lees Corner, Chestertown, MD 21620, USA
This Brand new townhome in Historic Chestertown will be available in just a few weeks! It features luxury vinyl flooring throughout, white shaker cabinets, granite counters, a spacious living room, an eat-in kitchen area, a covered patio off t...
$5,040
Available: Right Now
Listed: 04/05/2024
Chestertown, MD, 21620
You won’t forget your time in this romantic, memorable treehouse. A renovated 19th century carriage house, Owl Cottage is the perfect combination of historic ambience and modern convenience, all in the center of Chestertown.It features a 1st ...
$12,480
Available: Right Now
Listed: 01/05/2024
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...
$8,100
Available: Right Now
Listed: 30/04/2024
Chestertown, MD, 21620
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...
$19,500
Available: Right Now
Listed: 01/05/2024
Chestertown, MD, 21620
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, ...
$4,830
Available: Right Now
Listed: 01/05/2024
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...
$8,430
Available: Right Now
Listed: 01/05/2024
Chestertown, MD, 21620
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/...
$16,500
Available: Right Now
Listed: 04/05/2024
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...
$7,050
Available: Right Now
Listed: 04/05/2024
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...
$17,760
Available: Right Now
Listed: 04/05/2024
Chestertown, MD, 21620
BNB Breeze Presents Harbor View Haven! This exquisite waterfront property offers a captivating retreat to relax and recharge with stunning views and an array of desirable features! With a serene waterfront location, this idyllic home provides a p...
$4,650
Available: Right Now
Listed: 04/05/2024
Chestertown, MD, 21620
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. ...
$22,590
Available: Right Now
Listed: 30/04/2024
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...
$18,570
Available: Right Now
Listed: 01/05/2024
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...
$21,330
Available: Right Now
Listed: 01/05/2024
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...