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

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Check availability on Chestertown Beach Hotels

Tonight
18 Sep - 19 Sep
Tomorrow
19 Sep - 20 Sep
This weekend
18 Sep - 20 Sep
Next weekend
25 Sep - 27 Sep

Our top choices for Chestertown beach hotels

Premier Room | 1 bedroom, premium bedding, iron/ironing board, WiFi (free)
Premier Room | 1 bedroom, premium bedding, iron/ironing board, WiFi (free)
Breakfast and dinner served
Premier Room | Television

1. Friends Lake Inn

Friends Lake Inn
Chestertown
AED 453
AED 503 total
includes taxes & fees
21 Sep - 22 Sep
Friends Lake Inn
Exterior
BBQ/picnic area
Premium bedding, iron/ironing board (on request), WiFi (free)
Reception

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
19 Sep - 20 Sep
Pine Tree Motel & Cabins
Beach
Outdoor dining
TV, fireplace, offices
4 bedrooms, iron/ironing board, WiFi, bed sheets

3. The Lily Pad at Loon Lake near Gore Mountain

The Lily Pad at Loon Lake near Gore Mountain
Chestertown
AED 577
AED 1,663 total
includes taxes & fees
21 Sep - 22 Sep
The Lily Pad at Loon Lake near Gore Mountain
Front of property
Front of property - evening/night
Lunch and dinner served
Garden views, open select days

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
27 Sep - 28 Sep
Gore Mountain Lodge
Private beach, sun loungers, kayaking, rowing
Beautiful Lakefront Home | Living area | 43-inch flat-screen TV with cable channels
Sundeck
Property grounds

5. 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
23 Sep - 24 Sep
The Juliana Resort
Private beach, kayaking, motor boating
Exterior
Restaurant
Couples dining

6. Lodge at Schroon Lake

Lodge at Schroon Lake
Schroon Lake
AED 509
AED 695 total
includes taxes & fees
18 Oct - 19 Oct
Lodge at Schroon Lake
Private beach, sun loungers, beach umbrellas, kayaking
Exterior
32-inch TV with cable channels
Lakeview One-Bedroom Beach Suite | Terrace/patio

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.
AED 304
AED 338 total
includes taxes & fees
20 Sep - 21 Sep
Depe Dene Lakeside Resort
Reception
Seasonal outdoor pool, open 9 AM to 9:00 PM, pool umbrellas
Balcony
Exterior

8. Admiral Motel

Admiral Motel
Lake George
AED 294
AED 327 total
includes taxes & fees
20 Sep - 21 Sep
Admiral Motel
Indoor pool
Reception
Reception
Desk, blackout drapes, iron/ironing board, cribs (free)

9. Spark by Hilton Lake George Outlets

Spark by Hilton Lake George Outlets
Lake George
AED 358
AED 398 total
includes taxes & fees
24 Sep - 25 Sep
Spark by Hilton Lake George Outlets
Indoor pool, outdoor pool, open 9:00 AM to 10:00 PM, pool umbrellas
Exterior
Flat-screen TV, toys
Blackout drapes, iron/ironing board (on request), travel crib

10. 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.
AED 287
AED 330 total
includes taxes & fees
22 Sep - 23 Sep
Adirondack Retreat Inn & Suites
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

Tiki Resort

Tiki Resort

10/10 Excellent
"My family love it here! staff were very nice and accommodating! Definitely coming back :)"
Roche 1-night trip
Posted 2 hours ago
Tiki Resort
Lakefront Terrace Resort

Lakefront Terrace Resort

8/10 Good
"Good stay"
Luisa 2-night trip
Posted 4 hours ago
Lakefront Terrace Resort

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 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 like 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 center. If you'd like to venture out around the area, you may want to rent a car for your trip.