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Top hotels and accommodation in Chestertown

Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
8.6 out of 10, Excellent, (825)
The price is NZ$218
includes taxes & fees
3 Nov - 4 Nov

Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
7.2 out of 10, Good, (399)
The price is NZ$154
includes taxes & fees
12 Oct - 13 Oct

The Lodge at Great Oak Landing
The Lodge at Great Oak Landing
7.8 out of 10, Good, (70)
The price is NZ$259
includes taxes & fees
7 Oct - 8 Oct

Driftwood Inn
Driftwood Inn
5.2 out of 10, (174)
The price is NZ$121
includes taxes & fees
27 Oct - 28 Oct

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
7.0 out of 10, Good, (1003)
The price is NZ$152
includes taxes & fees
8 Oct - 9 Oct

Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG
9.2 out of 10, Wonderful, (903)
The price is NZ$242
includes taxes & fees
19 Oct - 20 Oct
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.

Photo by Assya A
Open Photo by Assya A
More cheap accommodation in Chestertown
More cheap accommodation in Chestertown

Hampton Inn Baltimore/Glen Burnie
6617 Ritchie Hwy, Glen Burnie, MD
The price is NZ$205 per night from 2 Nov to 3 Nov
NZ$205
2 Nov - 3 Nov
includes taxes & fees
8/10 Very Good! (1,007 reviews)