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Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.

Top rated by guests
Exterior
Private kitchen
Dining
Pool
Exterior detail
review stars
10Outstanding
(8 Ratings)
"This property was so much more than anticipated! Beautiful lawn, acres as far as you an see, secluded, private and very relaxing! Robert handled all our needs and was kind enough to share history ab..."
Diane W.
Don't miss out! Price and availability may change
10 / 10
Outstanding(8 Ratings)

Cottage in Maryland

6 guests · 3 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
High-end valueWell priced for this area

About this cottage rental

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 beautiful sunsets, birds, deer and more. The salt water pool is shared only with the main house on certain dates in the summer. Guests will have the pool area 6 hours a day to themselves (to Oct 1). Recently renovated and furnished. Outside back yard seating and eating area with BBQ. High speed fiber internet, smart TVs. 2 fat tire bikes available. Central AC and heat. Seating on dock and water with fire pit. Easy access, parking, ground floor Master.

Amenities at Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.

Non-smoking
Pets allowed
Family friendly

Map of Maryland

city location on map

Nearby attractions

Lincoln Memorial
51.7 mi
Smithsonian National Museum of Natural History
50.5 mi
National Museum of African American History and Culture
50.8 mi
Smithsonian National Air and Space Museum
50.2 mi

Ratings and reviews

10 / 10
Outstanding(8 Ratings)
10 / 10Outstanding·Jul 2025
This property was so much more than anticipated! Beautiful lawn, acres as far as you an see, secluded, private and very relaxing! Robert handled all our needs and was kind enough to share history about the property. We will be sure to visit again!
10 / 10Outstanding·Nov 2024
So delightful
10 / 10Outstanding·Oct 2024
This was our second stay in the cottage on this beautiful, serene property. If you are looking for comfortable and quiet but the option to go to town for dinner this is the place for you. I know we will be back!
10 / 10Outstanding·Sep 2024
lovely grounds
$$$$
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FAQs

Is parking included with this cottage?

Parking is not specified as an available amenity at Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.. For more information, we encourage you to contact the property about where to park.

Is there a pool at this cottage?

We didn’t find pool listed as an amenity for this cottage. It may be worth double checking if a pool is important for your stay.

Is Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock. pet friendly?

Yes! This cottage is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.?

We found 3 amenities for this rental. This includes non-smoking, pets allowed, and family friendly.