Chestertown Vacation Rentals
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Vacation Rentals in Chestertown

First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic Chestertown

The Heron's Nest at Atlantic Marina
The Heron's Nest at Atlantic Marina

Waterfront Oasis of Annapolis Star
Waterfront Oasis of Annapolis Star

Floating 2 bed 2 bath condo stunning views of the bay
Floating 2 bed 2 bath condo stunning views of the bay

Entire House by the Fells Point, JHU.
Entire House by the Fells Point, JHU.

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Chesapeake Houseboat Getaway on Kent Island, Maryland
Chesapeake Houseboat Getaway on Kent Island, Maryland

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Find out more about Chestertown
Find out more about Chestertown
Everything you need to know about Chestertown vacation rentals
Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chestertown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.
There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chestertown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
Chestertown vacation rentals: An excellent choice for every season
Whenever you want to travel, a warm welcome awaits you in Chestertown. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chestertown in high season.
Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $159 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!
How to find incredible deals on Chestertown rentals
At Expedia, we put the best Chestertown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.
To find some top Chestertown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chestertown vacation.
If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chestertown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.
Recent reviews of Chestertown properties
Recent reviews of Chestertown properties

Hampton Inn Baltimore/Glen Burnie
Explore a world of travel with Expedia
Explore a world of travel with Expedia
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