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Destination airport | Chestertown |
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Hotels in Chestertown
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
The price is NZ$206 per night from 3 Aug to 4 Aug
NZ$206
3 Aug - 4 Aug
includes taxes & fees
Stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (933 reviews)
"Room excellent, very clean, well stocked breakfast, nice outdoor pool with lots of privacy, great restaurants walking distance"
Reviewed on 13 July 2026
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
The price is NZ$262 per night from 23 July to 24 July
NZ$262
23 July - 24 July
includes taxes & fees
Stay at this beach lodge in Chestertown. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Pooles Island Light and Kinnairds Point Drive ...
8/10 Very good! (91 reviews)
"We love this place 😀….great pool nice room,free golf!!!!….in the middle of nowhere,but that’s nice…15 minutes to Chestertown…we come every year 👍"
Reviewed on 7 July 2026
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
The price is NZ$139 per night from 21 July to 22 July
NZ$139
21 July - 22 July
includes taxes & fees
Stay at this hotel in Chestertown. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff in their reviews. Popular attractions ...
7.2/10 Good! (462 reviews)
"Big room,very comfortable bed,direct tv….pool was out of order,apparently has been for quite a while…..enjoyed our stay😀"
Reviewed on 11 July 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.
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^Savings based on all package bookings made with Flight + Hotel on Wotif.co.nz from , as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.