Hotels in Chestertown, MD
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Showing 4 of 4 stays
Comfort Inn & Suites Chestertown
Chestertown, Maryland
ParkingGym
The Lodge at Great Oak Landing
Chestertown, Maryland
Free WiFiPool
Red Roof Inn & Suites Chestertown
Chestertown, Maryland
Free WiFiParking
Driftwood Inn
Chestertown, Maryland
Free WiFiParking
Most-reviewed hotels in Chestertown
the most-booked, by review volume
Why Chestertown hotels cost less here
Most travel sites quietly mark up your room — and some change the price based on your device, location or browsing history. We don't. You pay what the hotel charges us plus one small flat fee, and it's the same number for every traveler on every screen. No surveillance pricing. Ever.
Hotels in Chestertown: common questions
How many hotels are in Chestertown?
There are 4 hotels in Chestertown, MD on travelpluscost. The highest-rated right now is Comfort Inn & Suites Chestertown, with a 8.0/10 guest score from 459 reviews.
How does travelpluscost keep Chestertown hotels cheaper?
You pay what the hotel charges us plus one small flat fee — the same price for every traveler, on every device. We never raise the price based on your location, browser or history. That flat fee is usually less than the hidden markup most travel sites bake in.
Are taxes and resort fees included in the price?
Yes. Every room shows the all-in price — the nightly rate plus taxes and known fees — so the total you see is the total you pay. Where a Chestertown hotel charges a resort or property fee, it's already in that number.
Can I cancel a Chestertown hotel booking?
Many Chestertown hotels offer fully refundable rates. When a room can be cancelled for free we label it "Fully refundable", so you can spot a flexible rate at a glance.
All 4 hotels in Chestertown
Every stay we cover here — pick any to see live prices.