A waterfront town with a pier, dock, and several buildings.

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Check availability on Chestertown Beach Hotels

Tonight
6 Oct - 7 Oct
Tomorrow
7 Oct - 8 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Chestertown beach hotels

Room
Television
Restaurant
Property entrance

1. Friends Lake Inn

Friends Lake Inn
Chestertown
AED 453
AED 503 total
includes taxes & fees
27 Oct - 28 Oct
Friends Lake Inn
A small, single-story house with a gabled roof and a front porch.
A small wooden cabin with a porch and two chairs in front.
A wooden arbor structure in a grassy area with two potted plants.
A room with wooden walls, a bed, a dresser, a television, and a small refrigerator.

2. Pine Tree Motel & Cabins

Pine Tree Motel & Cabins
Chestertown
  • Unwind just a minute from the sandy shores of Loon Lake, where a serene beach retreat awaits with beach toys, firepit, and hiking trails.
AED 643
AED 713 total
includes taxes & fees
7 Oct - 8 Oct
Pine Tree Motel & Cabins
A person fishing by a lake with a boat in the background.
A bedroom with a large bed, two bedside lamps, a framed picture on the wall, and a nightstand with a lamp.
A living room with a fireplace, a television, a couch, and a plant.
Private lakefront access just down the road with two docks, a cozy firepit, and comfortable outdoor seating. Perfect for fishing, enjoying the view, or unwinding by the water.

3. The Lily Pad at Loon Lake near Gore Mountain

The Lily Pad at Loon Lake near Gore Mountain
Chestertown
AED 551
AED 1,631 total
includes taxes & fees
13 Oct - 14 Oct
The Lily Pad at Loon Lake near Gore Mountain
A wooden building with large windows and a metal roof.
A bar area with wooden windows, shelves of liquor bottles, and glasses.
A yurt interior with a central wood-burning stove, leather seating, and a traditional rug.
A wooden lodge with a snow-covered roof and multiple windows, surrounded by a snowy landscape and trees.

4. Gore Mountain Lodge

Gore Mountain Lodge
North Creek
  • Coastal adventure by day, cabin-style comfort by night at this state park motel, where serene sandy beaches await just steps from your door.
AED 493
AED 547 total
includes taxes & fees
20 Oct - 21 Oct
Gore Mountain Lodge
An indoor swimming pool with a view of the city through large windows, a seating area with chairs, and a ceiling with exposed beams.
A hotel room with a large bed, bedside tables, a desk, and a window with curtains.
A gym with treadmills, an elliptical, a bench press, a water dispenser, and a TV on the wall.
A residential area with two-story buildings, a well-maintained lawn, and a clear sky.

5. Spark by Hilton Lake George Outlets

Spark by Hilton Lake George Outlets
Lake George
AED 402
AED 446 total
includes taxes & fees
8 Oct - 9 Oct
Spark by Hilton Lake George Outlets
A beach with two people sitting on green chairs under a large umbrella, facing a lake with ducks swimming.
Two people sitting at a wooden table with a view of a lake and trees.
A dining area with a table set for four, large windows offering a view of a lake and trees, and a stone wall in the background.
A log cabin with a wooden porch and stone walls, surrounded by a well-maintained garden with various plants and flowers.

6. Lodge at Schroon Lake

Lodge at Schroon Lake
Schroon Lake
AED 509
AED 695 total
includes taxes & fees
1 Nov - 2 Nov
Lodge at Schroon Lake
A beach with white lounge chairs and a pier extending into the water.
A living room with a stone fireplace, leather furniture, and a chandelier.
A wooden building with a balcony, a clock, and a lifebuoy.
A waterfront deck with lounge chairs, a sailboat, and a dock extending into calm water.

7. The Juliana Resort

The Juliana Resort
Diamond Point
  • Escape to a pristine private beach with loungers, where kayaking, fishing, and water adventures await on the waterfront.
AED 338
AED 375 total
includes taxes & fees
7 Oct - 8 Oct
The Juliana Resort
A beach with rows of red chairs and a dock with boats.
A hotel room with a large bed, wooden flooring, a balcony with a view of the sea, and a ceiling fan.
An aerial view of a lakeside property with a dock, a gazebo, and a large house with a porch.
A modern living room with a sofa, coffee table, and artwork on the walls.

8. Depe Dene Lakeside Resort

Depe Dene Lakeside Resort
Lake George
  • Barefoot bliss awaits at this waterfront retreat with private beach access, beach loungers, and kayaking adventures on Lake George.
AED 327
AED 363 total
includes taxes & fees
7 Oct - 8 Oct
Depe Dene Lakeside Resort
A patio area with a stone fire pit, white outdoor furniture, and a white picket fence.
A hotel with a swimming pool, multiple lounge chairs, and a white fence surrounding the area.
A two-story building with a covered front porch, multiple balconies, and a landscaped garden in front.
A spacious kitchen with a central island, a chandelier, and a ceiling fan.

9. Quality Inn Lake George

Quality Inn Lake George
Lake George
AED 406
AED 450 total
includes taxes & fees
4 Nov - 5 Nov
Quality Inn Lake George
A hotel entrance with a stone facade, a covered entrance area, and a landscaped driveway.
A hotel pool area with lounge chairs and umbrellas, a clear sky, and a building with multiple windows.
A hotel room with a large bed, a bench, a TV, and a window with curtains.
A room with a wooden bench, a large tapestry, and a staircase leading to another room.

10. Comfort Inn & Suites Lake George

Comfort Inn & Suites Lake George
Lake George
  • Stroll mere minutes to Million Dollar Beach, where the shoreline beckons with golden sands and a chance to unwind along Lake George.
AED 371
AED 412 total
includes taxes & fees
1 Nov - 2 Nov
Comfort Inn & Suites Lake George
View all properties

Choose what matters most at beach hotels in Chestertown

Pool
Breakfast included
4 stars
5 stars
All-inclusive

Top Chestertown Hotel Reviews

The Georgian Lakeside Resort

The Georgian Lakeside Resort

10/10 Excellent
"C'était bien, honnêtement j'ai trouvé genre 2-3 cheveux et c'est pas mal ça. La trappe d'air au plafotde la salle de bain était entrain de se casser la figure et mangeait la poussière mais tout le reste était parfait. Le lit était Super confortable!!"
Marie-Pier 1-night trip
Posted 1 hour ago
The Georgian Lakeside Resort
Adirondack Retreat Inn & Suites

Adirondack Retreat Inn & Suites

8/10 Good
"It was beautiful and the hot tub in the room was heavenly"
Harold 2-night trip
Posted 5 hours ago
Adirondack Retreat Inn & Suites
Fort William Henry Hotel and Conference Center

Fort William Henry Hotel and Conference Center

10/10 Excellent
"Great place and views of the lake!"
Jason 4-night trip
Posted 2 days ago
Fort William Henry Hotel and Conference Center

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 Veterans Memorial Park Beach or Rogers 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.