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Beach Hotels in Chestertown

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Chestertown Hotels

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Featured Chestertown Beach Hotels

See all 125 Hotels in Chestertown
Friends Lake Inn

Friends Lake Inn

963 Friends Lake Rd, Chestertown
4.0 out of 5.0
5.0 out of 5 (1 reviews)
Great people Great FoodGreat Place Great people Great Food Really enjoyed the facility
  Feb 8, 2016

$199

$199
The Fern Lodge

The Fern Lodge

46 Fiddlehead Bay Rd, Chestertown
3.5 out of 5.0
4.2 out of 5 (4 reviews)
Great great little germ of an hotelWe had a great time. Great room, Great host, fabulous location
  Jul 13, 2014

$395

$395
Pine Tree Motel & Cabins

Pine Tree Motel & Cabins

5537 State Route 8, Chestertown
2.0 out of 5.0
3.9 out of 5 (12 reviews)
Super Cute & Affordable My boyfriend & I stayed in a cabin & it was perfect for the two of us! The bathroom was super clean, and so was the main room. Super cozy ADK style! We loved it.
  Oct 18, 2016

$135

$135
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Chestertown Beach Hotel Information

Swimsuit up and hit the surf when you book a beach hotel in Chestertown.
  • Browse our big collection of beach hotels to relish in an ocean view
  • Make your decision easier by checking out the verified and vetted consumer reviews
  • Rest easy knowing you have access to the lowest rates around

Life is a beach, so you might as well play in the sand. Sun worshippers and beach bums unite here on Expedia.com to find affordable accommodations on the water.

After all, those who adore the sea and sand understand the lure of a beach resort in Chestertown. Whether it’s the smell of the salty air from your balcony or the easy access to sand between your toes, a waterfront hotel takes your getaway up a notch.

Make a splash on your next coastal vacation when you treat yourself to a hotel on the beach near Chestertown. Just imagine waking up to the sun glistening on the water and falling asleep to the sound of crashing waves. During your seaside sojourn, give surfing a try or beachcomb for unscathed seashells during an early morning stroll. From building sand castles and biking on the boardwalk to watching for dolphins on the horizon and picnicking on the shore at sunset, these beachfront hotels dazzle with their close proximity to the coastal scene.

Take a look at our collection of beach hotels to soak up the sun on vacation without drying out your wallet. Here at Expedia.com, we offer great deals on Chestertown beach hotels. Because we understand you want to spend more on snorkeling excursions and less on your accommodation, we provide you with the hottest ocean views around. When you’re looking for a breadth of choice and a personalized beach getaway within your price range, turn to Expedia.