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$173 per night from 16 Nov to 17 Nov
AU$173
16 Nov - 17 Nov
includes taxes & fees
8.4/10 Very Good! (843 reviews)
Large clean room. Bed firm
Reviewed on 8 Nov 2025
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is AU$122 per night from 30 Nov to 1 Dec
AU$122
30 Nov - 1 Dec
includes taxes & fees
7.2/10 Good! (411 reviews)
its an average hotel with a clean bed to sleep in
Reviewed on 28 Oct 2025
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd, Chestertown, MD
Fully refundable
The price is AU$168 per night from 13 Nov to 14 Nov
AU$168
13 Nov - 14 Nov
includes taxes & fees
7.8/10 Good! (75 reviews)
Beautiful view
Reviewed on 8 Nov 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.
