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$169 per night from 9 July to 10 July
AU$169
9 July - 10 July
includes taxes & fees
8.6/10 Excellent! (921 reviews)
"Parking clean room"
Reviewed on 5 June 2026
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
The price is AU$113 per night from 21 June to 22 June
AU$113
21 June - 22 June
includes taxes & fees
7.2/10 Good! (455 reviews)
"The staff,( if you want to call them that)don't greet you when you walk in to register, I had to initiate the conversation. The elevator floor was filthy nasty and it creaked and groaned. We got off of the elevator on our floor and was greeted by Marijuana smoke and smell. I went back down to inform ..."
Reviewed on 7 June 2026
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
Fully refundable
The price is AU$215 per night from 16 June to 17 June
AU$215
16 June - 17 June
includes taxes & fees
7.8/10 Good! (86 reviews)
"This property is situated in a beautiful marina with excellent facilities. Guests staying at the Lodge can also enjoy complimentary golf, which was a great bonus. We thoroughly enjoyed our stay and would happily return. The only drawback was that the Wi-Fi service was somewhat inconsistent."
Reviewed on 6 June 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.
