$14,250
Available: Right Now
Listed: 23/04/2024
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...
$8,760
Available: Right Now
Listed: 26/04/2024
Chestertown, MD, 21620
Enjoy this oceanfront community at this 2000 sq ft Cape Code Home 4 bedrooms, 2.5 bathrooms with a bonus room with office and sofa sleeper with farm doors for semi-privacy. Has two electric fireplaces, firepit, gaming area with pool table with conver...
$8,250
Available: Right Now
Listed: 23/04/2024
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...
$7,920
Available: Right Now
Listed: 25/04/2024
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...
$11,670
Available: Right Now
Listed: 26/04/2024
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 ...
$19,290
Available: Right Now
Listed: 22/04/2024
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...
$16,500
Available: Right Now
Listed: 22/04/2024
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...
$34,800
Available: Right Now
Listed: 22/04/2024
Chestertown, MD, 21620
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. ...
$8,100
Available: Right Now
Listed: 23/04/2024
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: 26/04/2024
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, ...
$24,000
Available: Right Now
Listed: 22/04/2024
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...
$7,290
Available: Right Now
Listed: 22/04/2024
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...
$7,050
Available: Right Now
Listed: 22/04/2024
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...
$22,590
Available: Right Now
Listed: 24/04/2024
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: 26/04/2024
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...
$17,430
Available: Right Now
Listed: 26/04/2024
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...
$10,950
Available: Right Now
Listed: 26/04/2024
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 ...
$21,330
Available: Right Now
Listed: 26/04/2024
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...
$23,250
Available: Right Now
Listed: 23/04/2024
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 ...
$10,500
Available: Right Now
Listed: 26/04/2024
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...
$34,200
Available: Right Now
Listed: 26/04/2024
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...
$12,480
Available: Right Now
Listed: 26/04/2024
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...