Chestertown Holidays
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Your Chestertown Holiday
With one of our holiday packages to Chestertown, you'll find endless opportunities for relaxation and adventure. There's a lot to look forward to, including its colonial history and cultural experiences. Any trip to Chestertown needs a well-planned itinerary. Fill yours with major attractions like Washington College, Rolphs Wharf Marina and River Arts Chestertown. No matter your travel plans or budget, organising a tailored Chestertown holiday is simple with Expedia.
Chestertown Holiday
Chestertown Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 5,100 |
Max Temp Winter | 7ºC |
Max Temp Summer | 27ºC |
Top Sights | Historical Society of Kent County Maryland, Garfield Centre for the Arts at the Prince Theatre and Crow Farm and Vineyard |
Our pick of the best Chestertown Hotel Deals
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Fully refundableReserve now, pay when you stay
The price is AU$166 per night from 25 Jan to 26 Jan
AU$166
25 Jan - 26 Jan 2026
includes taxes & fees
8.4/10 Very Good! (860 reviews)
Very nice
Reviewed on 14 Dec 2025
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
The price is AU$119 per night from 4 Jan to 5 Jan
AU$119
4 Jan - 5 Jan 2026
includes taxes & fees
7.2/10 Good! (421 reviews)
Very clean. Pets allowed.
Reviewed on 14 Dec 2025
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,904 reviews)
Great customer service!
Reviewed on 21 Dec 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Chestertown
Wilmer Park
Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
