Destination
Hotels in Chestertown
23 properties
Compare 23 hotels in Chestertown on Hotels of Earth.
The "from" prices are indicative and refreshed regularly; the exact price for your dates is confirmed live the moment you open a hotel — and everything happens on Hotels of Earth itself, with no handoff to a third-party site.
8Comfort Inn & Suites Chestertown
★★ · 473 reviews
7.2Red Roof Inn & Suites Chestertown
★★ · 149 reviews
10The Fern Lodge
★★★★ · 46 reviews
9.1The Lodge at Loon Lake
★★ · 110 reviews
9.2Pine Tree Motel & Cabins
★★ · 77 reviews
8.5Friends Lake Inn
★★★★★ · 120 reviews
9.8Carriage House Hideaway In Center of Chestertown
6 reviews
9.7Brampton 1860
★★★★★ · 23 reviews
10Chestertown Hideaway w/ Lake & Beach Access!
★★★ · 1 reviews
7.6The Lodge at Great Oak Landing
★★★ · 48 reviews
5.2Driftwood Inn
★★ · 168 reviews
621 Mi to Gore Mtn: Adirondack Oasis w/ Sauna
★★★
6Rustic Adirondacks Home w/ Hot Tub & Lake Access!
★★★
6Tree Tops Retreat ~ 19 Mi to Lake George!
★★★
6Chestertown Retreat w/ Fire Pit, Near Gore Mtn!
★★★
6Pet-friendly Home on Chester River w/ Dock!
★★★
Eastern Shore Getaway: Walk to Tolchester Marina!
★★★
Loon Lake View: Newly Built Log Cabin w/ Fire Pit!
Family Gem: Private Community Beach on Tripp Lake
★★★
Mossy Bear Retreat
4 Mi to Beach & Lake: Spacious Home in Chestertown
★★★
Walk to Historic Chestertown: Dog-Friendly Retreat
★★★
Year-Round Loon Lake Retreat: Ski, Hike, Explore!
★★★
Good to know
- How current are the prices for Chestertown?
- The "from" prices here are refreshed regularly for a sample two-night stay; the exact price for your dates is confirmed live when you open a hotel.
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