Chestertown Holidays
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Top hotels in Chestertown
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Fully refundable
The price is S$161 per night from 25 May to 26 May
S$161
25 May - 26 May
includes taxes & fees
8.6/10 Excellent! (909 reviews)
Traveling on 301 to New England somewhat off the beaten path Service excellent
Reviewed on 28 Apr, 2026
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
The price is S$101 per night from 17 May to 18 May
S$101
17 May - 18 May
includes taxes & fees
7.2/10 Good! (440 reviews)
Clean lady was nice help me out
Reviewed on 26 Apr, 2026
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
Fully refundable
The price is S$184 per night from 13 May to 14 May
S$184
13 May - 14 May
includes taxes & fees
7.8/10 Good! (80 reviews)
A lovely spot with views of the marina. We went in the offseason, so there were very few hotel guests and the price was extremely reasonable. Memory foam mattresses. Nothing fancy, but it had a small fridge and free coffee from a station in the hall. Note: no elevator, so if mobility is an issue, ...
Reviewed on 23 Apr, 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 package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
