Chestertown Countryside Home on the Eastern Shore! | Other in Chestertown

Make the former & newly restored historic Hilltop Hotel your weekend home in the countryside of the Eastern Shore, Maryland. The hotel was visited by guests who would spend time at Tolchester Beach just a few minutes down the road. Now, you and your guests can spend time relaxing in the outdoor oasis on the wrap around porch, patio & sprawling acres with beautiful views. A perfect getaway with friends or family. The home was completely renovated in 2021 while preserving the charm and history of the property.

Accommodations: Six Bedrooms, three and one half baths, open living & dining room, study, full kitchen, back yard patio with gas grill, fire pit, wrap around porch, sleeps 14.

The home is centrally located between historic Chestertown, MD and the beautiful marinas of Rock Hall, MD. Arrive at either location within minutes. Enjoy countryside privacy yet the convenience of accessing downtown shops, waterfront restaurants, cafes, boating and marinas, beaches, farmer’s market, and terrific wineries. All while experiencing the history and charm that the Eastern Shore has to offer! This is a fantastic property for those wishing to explore the Eastern Shore, visiting for a wedding or gathering with friends for a weekend getaway.

Chestertown:
The Kitchen at the Imperial
The Retriever Bar
Watershed
Bad Alfred’s Distilling
Casa Carma Wine
Play it Again Sam Cafe
Modern Stone Age Kitchen
Figg’s Ordinary
Evergrain Bread & Coffee

Rock Hall:
Harbor Shack
Watermens Crab House
Passages Bar & Grill
Admirals Club Beachside Bar at Haven Harbour South
Osprey Point Restaurant & Marina
Java Rock Coffee House & Cafe

Wineries:
Crow Winery & Vineyard
Lands Point Winery & Vineyard

Activities / Explore:
Blue Crab Chesapeake Bay - Sailing Cruises
Waterman’s Museum
Eastern Shore Wildlife Refuge

History & Local Information:
Chestertown, MD is located on the Chester River, a tributary of the Chesapeake Bay, founded in 1706. Located along Maryland’s beautiful Eastern Shore, Chestertown has a vibrant arts district, rich with history and culture, delicious restaurants, cafes and lively entertainment along with quaint boutique stores providing for a wonderful shopping experience. The historic tree-lined streets and beautiful brick sidewalks bring you back to the colonial times when Chestertown was founded.

Chestertown is known for its many festivals and events including First Friday, Tea Party, Downrigging Weekend, the Harry Potter Festival, and the famous Saturday morning Farmers Market which is a must to visit.

Rock Hall, MD otherwise known as the “Pearl of the Chesapeake” is a beautiful waterfront town located on the Chesapeake Bay. Like Chestertown, Rock Hall has its own rich history dating back to 1707. Originally called Rock Hall Cross Roads in a nod to it’s main street which was part of the first road cut in Kent County in 1675. Both George Washington and Thomas Jefferson passed through these streets several times on their way to and from the Continental Congress in Philadelphia, PA. Rock Hall has long played an important part of the Eastern Shore. Today, the town remains a working harbor for commercial waterman, a robust seafood and fishing industry, beautiful marinas, destination for boating and sailing with waterfront dining and entertainment.

We know that you will enjoy and come to love our beautiful home as much as we have. We ask that you kindly respect the home and property. Have a wonderful time visiting the Eastern Shore, MD!

Chestertown Countryside Home on the Eastern Shore! is located in Chestertown. Chestertown Countryside Home on the Eastern Shore! provides accommodation, featuring Laundry, Air Conditioner, Bedding/Linens, among other amenities. This Other features Laundry, Air Conditioner, Bedding/Linens, to make your stay a comfortable one.

Chestertown Countryside Home on the Eastern Shore! has 6 Bedrooms , 4 Bathrooms, and max occupancy of 14 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated Other because of the excellent services rendered by the owner or manager of this Other, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. Other has a friendly neighborhood, and the Chestertown has interesting places to visit. If you want to learn more about the Other in Chestertown, such as places to visit and things to do nearby, you can check below to learn more.