Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

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Check availability on Chestertown Beach Hotels

Next weekend
26 Jun - 28 Jun
In two weeks
3 Jul - 5 Jul

Our top choices for Chestertown beach hotels

Premier Room | 1 bedroom, premium bedding, individually decorated

Friends Lake Inn

Friends Lake Inn
4.0 star property
Chestertown
8.8 out of 10, Excellent, (105 reviews)
The price is AED 620
AED 688 total
includes taxes & fees
22 Jun - 23 Jun
Friends Lake Inn
Exterior

Pine Tree Motel & Cabins

Pine Tree Motel & Cabins
2.0 star property
Chestertown
9.2 out of 10, Wonderful, (146 reviews)
  • cleanliness
    Unwind just a minute from the sandy shores of Loon Lake, where a serene beach retreat awaits with beach toys, firepit, and hiking trails.
The price is AED 643
AED 713 total
includes taxes & fees
22 Jun - 23 Jun
Pine Tree Motel & Cabins
Exterior

Luzerne Court Motel

Luzerne Court Motel
2.5 star property
Lake Luzerne
9.4 out of 10, Exceptional, (319 reviews)
The price is AED 371
AED 412 total
includes taxes & fees
23 Jun - 24 Jun
Luzerne Court Motel
Private beach, sun loungers, kayaking, rowing

The Juliana Resort

The Juliana Resort
2.5 star property
Diamond Point
8.8 out of 10, Excellent, (185 reviews)
  • cleanliness
    Escape to a pristine private beach with loungers, where kayaking, fishing, and water adventures await on the waterfront.
The price is AED 400
AED 444 total
includes taxes & fees
22 Jun - 23 Jun
The Juliana Resort
Premium Room | Premium bedding, down comforters, individually decorated

The Alpine Lodge

The Alpine Lodge
3.0 star property
North Creek
9.0 out of 10, Wonderful, (683 reviews)
  • cleanliness
    Escape to the shore just steps away from this alpine retreat, where sandy beaches meet adventure on the water.
The price is AED 428
AED 515 total
includes taxes & fees
22 Jun - 23 Jun
The Alpine Lodge
Deluxe Room, 2 Queen Beds, Refrigerator & Microwave | Laptop workspace, iron/ironing board, free WiFi, bed sheets

Motel 6 Lake George, NY – Adirondacks

Motel 6 Lake George, NY – Adirondacks
2.5 star property
Lake George
9.0 out of 10, Wonderful, (184 reviews)
  • cleanliness
    Soak up the sun just minutes from the beach, with poolside relaxation and adventure trails that make this motel a perfect family escape.
The price is AED 268
AED 298 total
includes taxes & fees
30 Jun - 1 Jul
Motel 6 Lake George, NY – Adirondacks
Free daily continental breakfast

Best Western of Lake George

Best Western of Lake George
2.5 star property
Lake George
7.6 out of 10, Good, (1,002 reviews)
The price is AED 305
AED 339 total
includes taxes & fees
22 Jun - 23 Jun
Best Western of Lake George
Property amenity

Country Inn & Suites by Radisson, Lake George (Queensbury), NY

Country Inn & Suites by Radisson, Lake George (Queensbury), NY
3.0 star property
Queensbury
9.0 out of 10, Wonderful, (1,446 reviews)
  • cleanliness
    Seaside splendor awaits just minutes from this Lake George retreat, where beach days blend with pool relaxation and outdoor adventures.
The price is AED 433
AED 480 total
includes taxes & fees
24 Jun - 25 Jun
Country Inn & Suites by Radisson, Lake George (Queensbury), NY
Family Studio Suite | Free WiFi, bed sheets

Countryside Inn

Countryside Inn
2.5 star property
Lake George
6.8 out of 10, (213 reviews)
The price is AED 239
AED 266 total
includes taxes & fees
28 Jun - 29 Jun
Countryside Inn
Shower, free toiletries, hair dryer, towels

Howard Johnson by Wyndham Lake George

Howard Johnson by Wyndham Lake George
2.0 star property
Lake George
8.2 out of 10, Very Good, (1,004 reviews)
The price is AED 257
AED 285 total
includes taxes & fees
22 Jun - 23 Jun
Howard Johnson by Wyndham Lake George
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.
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Choose what matters most at beach hotels in Chestertown

Pool
Breakfast included

Top Chestertown Hotel Reviews

Six Flags Great Escape Lodge & Indoor Waterpark

Six Flags Great Escape Lodge & Indoor Waterpark

10/10 Excellent
"We brought our grandchildren, 5 & 12, they had a blast! The waterpark is getting an update in the Fall, you can see where it’s needed. The kids certainly don’t notice. The lazy river could use more tubes, but it had a good current and the water was warm. Lifeguards were alert all the time. If you want to eat breakfast there, prepare for a long waiting line. Starbucks is there with 1 employee, again long wait time. We had a Suite on the 4th floor, it was very clean, the beds and pillows were very comfortable."
Gina 1-night trip
Posted less than an hour ago
Six Flags Great Escape Lodge & Indoor Waterpark

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Frequently asked questions

What is Chestertown like for travelers who love the beach?
Known for its lakeside setting, Chestertown offers a lot for the traveler planning a getaway.
What's the best accommodation to stay near the beach in Chestertown?
The Fern Lodge is a top beach B&B with free breakfast and 8 hot tubs, and it's located close to Loon Lake Beach.
When's the best time for a beach vacation in Chestertown?
Plan your trip to the beach with a look at the seasons in Chestertown: The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chestertown are January, March, November, and December, with each month seeing an average of 13 inches of snowfall.
What is there to see and do around Chestertown?
After arriving and checking into your hotel, you'll probably want to explore your surroundings. If you're eager to check out the beaches, head to Rogers Memorial Park Beach or Veterans Memorial Park Beach for some relaxation by the water. Discover the area's lakeside setting, and make time for local attractions like Loon Lake Beach and Friends Lake. Other things to see and do in the area are Loon Lake and Hudson River.
What's the best way to get to my beach hotel in Chestertown?
Here's some information to help you get to and around your beach accommodation in Chestertown more easily: Make your way to Chestertown with a flight to Glens Falls, NY (GFL-Floyd Bennett Memorial), the closest major airport which is located 23.6 mi (38 km) from the city center. If you'd like to venture out around the area, you may want to rent a car for your trip.