Chestertown Vacation Rentals
Vacation Rentals in Chestertown
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Pool and Bay Views on wrap around deck in Kent Island
Firefly Cottage at the Cape, HOT TUB, community beach, back yard fun, Dads day
Chesapeake Houseboat Getaway on Kent Island, Maryland
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Directly Across from Gate One & Steps from the Waterfront
Cozy and peaceful BASEMENT in a house, close to different restaurants and a park
Waterfront Cottage on the Eastern Shore
Relax on Kent Island in 3 Bedroom Home w/Waterview
Annapolis Condominium in the heart of the historic center
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.
Waterfront Oasis of Annapolis Star
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Chestertown Vacation Rental Travel Info
Popular accommodation | Chestertown private vacation homes |
---|---|
Known landmarks | Historical Society of Kent County Maryland, Garfield Center for the Arts at the Prince Theater and Washington College |
International airport | Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) |
Other types of properties in Chestertown you may be interested in
Comfort Inn & Suites Chestertown
You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chestertown. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.
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