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Chestertown Vacation Rentals

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Vacation Rentals in Chestertown

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Top Chestertown Hotel Reviews

The Inn at Henderson's Wharf, Ascend Hotel Collection

The Inn at Henderson's Wharf, Ascend Hotel Collection

10/10 Excellent
"This super cute hotel is located on a dead end street on a harbor. Which is very pretty and quiet. The lobby is decorated really nicely. The front desk lady diamond was super sweet when I was checking in. I was served with a free check-in cocktail. Front desk clerk Cory was also exceptionally nice and helpful during my stay.The hotel offers breakfast daily and it is adequate. I really enjoyed the fruit parfait and granola every day. But it was stocked with hard-boiled eggs, bagels, muffins, coffee, and tea selection. The location was perfect for my stay. Walkable to many restaurants and sites. My room was clean and classically designed."
Cher 3-night trip
Posted 2 days ago
The Inn at Henderson's Wharf, Ascend Hotel Collection

Frequently asked questions

Are there vacation rentals in Chestertown?

Yes, we offer vacation rentals in Chestertown close to Crumpton Auction, or you can go with a more secluded option if you're looking for extra privacy while you relax. Chestertown is known for its sporting events and university setting. Make sure you have time to check out the festivals and art during your trip.

How many vacation rentals are there in Chestertown?

Expedia has 25 vacation rentals for your stay in Chestertown.

What can I see and do in Chestertown?

Enjoy the outdoors at Chestertown Dog Park and Urieville Park, or simply take in cultural attractions like Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater. Rolphs Wharf Marina and Chestertown Historic District are other places to visit while you're in town.

What are vacation rentals like in Chestertown?

Vacation rentals are private properties you can stay in for a couple days or more in Chestertown. Vacation rentals feature extras such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a family getaway.