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$158 per night from 1 Mar to 2 Mar
AU$158
1 Mar - 2 Mar
includes taxes & fees
8.4/10 Very Good! (872 reviews)
Polite and kind hotel manager
Reviewed on 25 Jan 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (1,885 reviews)
Everything about this beautiful historic hotel was beautiful and perfect—I can’t wait to come back!
Reviewed on 31 Jan 2026
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
4 Philadelphia Ct Rosedale MD
Fully refundableReserve now, pay when you stay
The price is AU$106 per night from 17 Feb to 18 Feb
AU$106
17 Feb - 18 Feb
includes taxes & fees
7/10 Good! (1,154 reviews)
Very nice stay, staff was very understanding and breakfast was amazing. Room was clean and we had no problems.
Reviewed on 4 Feb 2026
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.
