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Find Beach Resorts in Chestertown, MD
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Top Chestertown Beach Resorts & Hotels
Our top choices for Chestertown beach hotels

Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
8.6 out of 10, Excellent, (797)
The price is £90
includes taxes & fees
7 Sept - 8 Sept

Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
7.2 out of 10, Good, (386)
The price is £59
includes taxes & fees
27 Aug - 28 Aug

Driftwood Inn
Driftwood Inn
5.2 out of 10, (172)

The Lodge at Great Oak Landing
The Lodge at Great Oak Landing
8.0 out of 10, Very good, (65)
The price is £109
includes taxes & fees
26 Aug - 27 Aug

First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (98)
The price is £121
includes taxes & fees
25 Aug - 26 Aug

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
9.8 out of 10, Exceptional, (83)

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
10.0 out of 10, Exceptional, (81)

Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
9.8 out of 10, Exceptional, (22)
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.
Find out more about Chestertown
Top Chestertown Hotel Reviews

Comfort Inn & Suites Chestertown
10/10 Excellent
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