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 refundable
The price is AU$180 per night from 12 Apr to 13 Apr
AU$180
12 Apr - 13 Apr
includes taxes & fees
8.6/10 Excellent! (891 reviews)
Frindly staff. Slight noise but not bad. Rooms clean and comfortable.
Reviewed on 25 Mar 2026
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Chestertown MD
10/10 Exceptional! (16 reviews)
We brought our Lab with us. She loved looking out all the windows. She was afraid to walk up the open stairs but was content to sleep on the first floor. We enjoyed our stay at Outrange. Very quiet and secluded. Short walk to River.
Reviewed on 22 Mar 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
The price is AU$236 per night from 2 Apr to 3 Apr
AU$236
2 Apr - 3 Apr
includes taxes & fees
9/10 Wonderful! (1,863 reviews)
Clean room, friendly staff, and the PERFECT location for walking downtown Annapolis.
Reviewed on 24 Mar 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.
