Explore beach hotels in Chestertown, MD

We have 271 honest, unfiltered reviews from genuine customers you can check out, with an average review rating of 9.4.

Use our ocean view filter to see the Chestertown beach hotels that offer spectacular views. From cliffside panoramas to beach view hotels with rooms overlooking the sand. Check out poolside and tranquil garden views, too.

Currently, we have resorts and hotels in Chestertown on the beach going from a night to for top-end luxury. Prices vary depending on your travel dates, amenities, and neighborhood.

Filter your search results by clicking on the family friendly filter to see kid-friendly amenities and activities. From beach resorts with kids’ clubs to beachfront hotels offering fun watersports—you have plenty of choice.

With great deals on a vast selection of Chestertown beachfront hotels, 24/7 customer service, and the ability to bundle your hotel, flights, and car rental to save more—Travelocity makes it easy.

Many Chestertown hotels on the beach have pools. You can choose which amenities you want and use our pool filter to see the Chestertown beach hotels that have pools on site.

The best time to visit Chestertown for local events and activities is .

Prices for Chestertown beach hotels currently start at just a night. With 5 Chestertown beach hotels to choose from, you have stacks of tempting options, whatever your budget.

Enjoy swimming, reading, and sunbathing on the beach in Chestertown. There’s also action-packed beach fun and watersport adventures, too. Check each hotel’s information section to find out what’s available.

Pop in your travel dates and hit search and hunt though our fantastic deals on Chestertown beach resorts and beachfront hotels. Download the free Travelocity appOpens in a new window for awesome member discounts.