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

Search Beach Resorts & Hotels in Chestertown

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Beach Resorts & Hotels

Tonight
27 Sept - 28 Sept
Tomorrow
28 Sept - 29 Sept
Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct

Our top choices for Chestertown beach hotels

1. Friends Lake Inn

Friends Lake Inn
Chestertown
₹10,507
₹11,663 total
includes taxes & fees
29 Sept - 30 Sept
Friends Lake Inn

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.
₹16,769
₹18,613 total
includes taxes & fees
28 Sept - 29 Sept
Pine Tree Motel & Cabins

3. 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.
₹12,850
₹14,262 total
includes taxes & fees
28 Sept - 29 Sept
Gore Mountain Lodge

4. 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.
₹8,816
₹9,785 total
includes taxes & fees
28 Sept - 29 Sept
The Juliana Resort

5. Lodge at Schroon Lake

Lodge at Schroon Lake
Schroon Lake
₹13,439
₹18,326 total
includes taxes & fees
26 Oct - 27 Oct
Lodge at Schroon Lake

6. Spark by Hilton Lake George Outlets

Spark by Hilton Lake George Outlets
Lake George
₹10,491
₹11,644 total
includes taxes & fees
1 Oct - 2 Oct
Spark by Hilton Lake George Outlets

7. 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.
₹9,400
₹10,433 total
includes taxes & fees
5 Oct - 6 Oct
Depe Dene Lakeside Resort

8. Adirondack Retreat Inn & Suites

Adirondack Retreat Inn & Suites
Lake George
  • Bask in lakeside bliss with beach toys for sandy adventures, just minutes from Lake George and paddleboarding paradise.
₹9,087
₹10,450 total
includes taxes & fees
30 Sept - 1 Oct
Adirondack Retreat Inn & Suites

9. Admiral Motel

Admiral Motel
Lake George
₹7,675
₹8,520 total
includes taxes & fees
28 Sept - 29 Sept
Admiral Motel
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

Howard Johnson by Wyndham Lake George

Howard Johnson by Wyndham Lake George

8/10 Good
"This place appears to be undergoing renovations and updating of the rooms. The staff were very pleasant and helpful. Excellent location for our visit. Within a short walking distance to all the main Lake George attractions. There were a few minor room issues. 1st being that it was very small. 2nd NO towel bars in the bathroom and no bath towels on check in. 3rd there was 2 night stands but only 1 lamp. Lastly ..... the toilet seat was so loose it would slide sideways. kinda freaked out my GF on 1st use."
Richard 3-night trip
Posted 12 hours ago
Howard Johnson by Wyndham Lake George
Surfside On The Lake

Surfside On The Lake

10/10 Excellent
"Nice place, close to everything, easy parking"
Renee 2-night trip
Posted 15 hours ago
Surfside On The Lake
Adirondack Retreat Inn & Suites

Adirondack Retreat Inn & Suites

10/10 Excellent
"Just a quick stay for sleeping. Arrived in the evening to a spotless, well kept room and polite staff. All we needed for our quick stay."
April 1-night trip
Posted 15 hours ago
Adirondack Retreat Inn & Suites
Lakefront Terrace Resort

Lakefront Terrace Resort

10/10 Excellent
"2nd time here always a good experience great view and amenities"
Dashan 2-night trip
Posted 18 hours ago
Lakefront Terrace Resort
Pine Tree Motel & Cabins

Pine Tree Motel & Cabins

8/10 Good
"Charming old fashion Adirondack rustic style / decor individual small cabins (also has motel-styled rooms) - parking either in front of rooms or between cabins, a couple of minutes outside Chestertown, NY, 30 minutes from Schroon Lake, and 45 minutes from Ticonderoga (StarTrek Museum & Fort). Very nice, friendly, and accomidating owners / operators. Breakfast / coffee place "Two Sparrows" 5 minutes down the road. Driveway very well lite / marked at night, although wish those lights had either dimmed or turned off post midnight for a better / darker sleep . . . As it was a very wet / rainy, and cold night - heat worked very qickly / well and found extra pillows and blanket. Plenty of hot water in sink / shower, soap, shampoo, small college refrigerator and microwave provided, however no hairdryer for partner . . . Did not test WiFi as we only stayed for 8 hours total time. Would have wished to have had more time to explore grounds and Chestertown itself."
Ralf 1-night trip
Posted 1 day ago
Pine Tree Motel & Cabins
The Georgian Lakeside Resort

The Georgian Lakeside Resort

10/10 Excellent
"Everything was great....the staff was friendly, and very helpful.......will be back"
Russel 3-night trip
Posted 2 days ago
The Georgian Lakeside Resort
Super 8 by Wyndham Lake George/Downtown

Super 8 by Wyndham Lake George/Downtown

8/10 Good
"👍"
Shaheen 2-night trip
Posted 5 days ago
Super 8 by Wyndham Lake George/Downtown

Frequently asked questions

What is Chestertown like for travellers who love the beach?
Known for its lakeside setting, Chestertown offers a lot for the traveller planning a getaway.
What's the best accommodation option 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 holiday 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 temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chestertown are January, March, November and December, with each month seeing an average of 33 cm 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 Loon Lake Beach or Veterans Memorial Park Beach for some relaxation by the water. Discover the area's lakeside setting, and make time for local attractions such as Friends Lake and Loon Lake. Other things to see and do in the area are Hudson River and Tripp Pond.
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 centre. If you'd like to venture out around the area, you may want a rental car for your journey.

Explore a world of travel with Expedia