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$168 per night from 26 July to 27 July
AU$168
26 July - 27 July
includes taxes & fees
8.6/10 Excellent! (926 reviews)
"Comfortable beds. Breakfast was decent, with hot and cold options. Shower did not have pressure. Pool was small but nice. Unfortunately we were there Wednesday -Sunday and never were given new towels or a room cleaning. And the last morning we found ants in the room."
Reviewed on 14 June 2026
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
The price is AU$116 per night from 7 July to 8 July
AU$116
7 July - 8 July
includes taxes & fees
7.2/10 Good! (458 reviews)
"The property is a little older and could benefit from a good deep cleaning of carpets and upholstery, but the bed and bathroom were clean and the staff were great. Considering the price of other accomodations in the area it's an excellent value for the money if you're just looking for a clean place ..."
Reviewed on 22 June 2026
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
Fully refundable
The price is AU$219 per night from 30 June to 1 July
AU$219
30 June - 1 July
includes taxes & fees
7.8/10 Good! (88 reviews)
"Old facility but everywhere clean. There have a private beach. It was so nice. So cute place but restaurants are closed weekday. Microwave and coffee are not in room.AC was noisy."
Reviewed on 16 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.
Stay near popular Chestertown attractions
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
