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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Chestertown lodges

A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.

1. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
8.0 out of 10, Very good, (129 reviews)
"Great place! Clean, comfortable and in a beautiful area. I won’t stay anywhere else when I’m in that area."
United States
William
The price is £92
includes taxes & fees
12 Nov - 13 Nov
The Lodge at Great Oak Landing
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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Learn more about Chestertown

Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbour.

See all hotels in Chestertown
A lakeside town with a marina, a bridge, and a mix of residential and commercial buildings.