Explore beach hotels in Chestertown, MD from $115
Seize Your Someday with our amazing deals for the whole family!
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Top Chestertown Beach Resorts & Hotels
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Travelers like: close to beach, beach towels
Friendly owners and neighbors on a very quiet private road with unbeatable river views and access. The fishing right off the dock is great.
Reviewed on Oct 27, 2025
Comfort Inn & Suites Chestertown
staff is nice and place is good. proce wise is excellent
Reviewed on Jan 23, 2026
Beach Condos in Chestertown
BEACH WITHOUT THE BUSTLE
Beach Villas in Chestertown
Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach
How to find the best Chestertown beach hotels?
We have 930 honest, unfiltered reviews from genuine customers you can check out, with an average review rating of 9.1.
How can I find Chestertown beach hotels with nice views?
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.
How much does it cost to stay in a beach hotel in Chestertown?
Currently, we have resorts and hotels in Chestertown on the beach going from $115 a night to $871 for top-end luxury. Prices vary depending on your travel dates, amenities, and neighborhood.
How do I find Chestertown beach hotels that are good for families?
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.
Why should I book my beach hotel in Chestertown with Travelocity?
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.
Do any beach hotels in Chestertown have a pool?
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.
When is the best time to stay in a beach hotel in Chestertown?
The best time to visit Chestertown for local events and activities is .
Are there cheap beach hotels in Chestertown?
Prices for Chestertown beach hotels currently start at just $115 a night. With 4 Chestertown beach hotels to choose from, you have stacks of tempting options, whatever your budget.
What are some great things to do in Chestertown by the beach?
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.
How can I find the best beach hotels deals in Chestertown?
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.
Popular Beach Stays in Chestertown
Recent Chestertown Hotel Reviews By Fellow Wanderers
