Chestertown Beach hotels with AARP Discounts

Photo by Julie Miller

Featured Chestertown Beach Hotels

Friends Lake Inn

Friends Lake Inn

4 out of 5
963 Friends Lake Rd, Chestertown, NY
Friends Lake Inn
The Fern Lodge

The Fern Lodge

3.5 out of 5
46 Fiddlehead Bay Rd., Chestertown, NY
The Fern Lodge
Pine Tree Motel & Cabins

Pine Tree Motel & Cabins

2 out of 5
5537 State Route 8, Chestertown, NY
Pine Tree Motel & Cabins
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.
Chestertown, New York, United States of America
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Beach Hotels in Chestertown

When you can't wait to get to the beach, a trip to Chestertown is exactly what you need. Whether you're after a low-key hideaway or an island resort, Chestertown and the surrounding area has something for every traveler. With AARP Travel Center Powered by Expedia®, it will be easy to find something close to the area's main attractions. We combine members-only discounts with the best rates from Expedia, offering you the best price in travel, guaranteed.

Get the Most from Your Chestertown Vacation

When you vacation in Chestertown, there is one thing at the top of your list—the beach. Why not try to get as much time by the water as you can? Not only do these Chestertown beach hotels have a great location, but they also have amenities that'll help make your trip enjoyable from start to finish. Want to get more information on where to stay? Check out our guest reviews and ratings for the best accommodations. Using AARP Travel to book your hotel, you can get exclusive rates on hotels, car rentals and cruises, plus pay no booking fees on flights.

You might want to venture out and explore once you're settled. When it's time to head to the beach, grab your chairs and umbrella, and don't forget your sunblock. After a couple days on the beach, you might need some other things to do to keep you and the family entertained. Here's a list of several things to do if you want a break from the sand:

  • Magic Forest
  • Wildwest Ranch & Western Town
  • Six Flags Great Escape & Splashwater Kingdom
  • Six Flags Great Escape Lodge & Indoor Waterpark
  • Killington Resort

Between the beach and these parks, you will have no shortage of excursions to keep you amused on your trip.

Book Your Beach Hotel in Chestertown Today

When you are ready to kiss the cold goodbye, book a trip to the beach. We have hotels in Chestertown near the beach where you can shed snow boots for sandals at last. Book your Chestertown beach hotel today, and see what the AARP Travel Center Powered by Expedia® has in store for you.