Find beach hotels in Chestertown, NY from CA $103

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check availability on Chestertown Beach Hotel

Next weekend
In two weeks

Our top choices for Chestertown beach hotels

Friends Lake Inn

Friends Lake Inn
4.0 star property
Chestertown
8.8 out of 10, Excellent, (104 reviews)
"Friendly staff, room was clean, well maintained. Ate at the restaurant, food was great. "
United States
Erin
The price is CA $207
CA $230 total
includes taxes & fees
May 25 - May 26
Friends Lake Inn

Lily Pad North at Loon Lake near Gore Mountain

Lily Pad North at Loon Lake near Gore Mountain
Chestertown
9.6 out of 10, Exceptional, (30 reviews)
"Great stay with our family of 5, the house was well equipped, clean, and communication was seamless. Will stay again this winter."
United States
Kiera C.
The price is CA $138
CA $350 total
includes taxes & fees
May 25 - May 26
Lily Pad North at Loon Lake near Gore Mountain

Lily Pad South at Loon Lake near Gore Mountain

Lily Pad South at Loon Lake near Gore Mountain
Chestertown
9.8 out of 10, Exceptional, (49 reviews)
"Use of boats, canoes, and kayaks, all included, and just a few minutes to the sandy town beach."
United States
Jacqueline W.
The price is CA $152
CA $367 total
includes taxes & fees
Jun 1 - Jun 2
Lily Pad South at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain
Chestertown
10.0 out of 10, Exceptional, (118 reviews)
"The public beach was close by as well as the boating area which had plenty of canoes and kayaks for a large group."
United States
Pam R.
The price is CA $374
CA $1,002 total
includes taxes & fees
May 26 - May 27
Eagles Nest at Loon Lake near Gore Mountain

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.
"Wonderful friendly owners and probably the cleanest place I’ve ever stayed! And they are dog friendly! "
United States
James
The price is CA $242
CA $268 total
includes taxes & fees
May 25 - May 26
Pine Tree Motel & Cabins

The Lily Pad at Loon Lake near Gore Mountain

The Lily Pad at Loon Lake near Gore Mountain
Chestertown
9.6 out of 10, Exceptional, (41 reviews)
"My family enjoyed our stay. Close to the beach, private dock & boats down the road. Loon Lake was beautiful. The house was spacious, well stocked, clean, great outdoor space. Loved sitting in the ADK chairs near the firepit. Had something for everyone. Great for my young grandchildren. It was relaxing and peaceful."
United States
Deborah G.
The price is CA $220
CA $627 total
includes taxes & fees
Jun 1 - Jun 2
The Lily Pad at Loon Lake near Gore Mountain

The Juliana Resort

The Juliana Resort
2.5 star property
Diamond Point
8.8 out of 10, Excellent, (180 reviews)
  • cleanliness
    Escape to a pristine private beach with loungers, where kayaking, fishing, and water adventures await on the waterfront.
"The beach is breathtakingly gorgeous."
United States
Kristen
The price is CA $127
CA $141 total
includes taxes & fees
May 25 - May 26
The Juliana Resort

Luzerne Court Motel

Luzerne Court Motel
2.5 star property
Lake Luzerne
9.4 out of 10, Exceptional, (319 reviews)
"We stayed 2 nights. It was clean and comfortable. It smelled like cigarettes when we first got there but it got better once we aired it out. The people were nice and the pool was also good."
United States
Martin
The price is CA $151
CA $167 total
includes taxes & fees
May 25 - May 26
Luzerne Court Motel

The Alpine Lodge

The Alpine Lodge
3.0 star property
North Creek
9.0 out of 10, Wonderful, (680 reviews)
  • cleanliness
    Escape to the shore just steps away from this alpine retreat, where sandy beaches meet adventure on the water.
"Would highly recommend! Comfortable, clean and spacious. Enjoyed the chairs on the balcony, the flat screen tv and Alexa. Thank you!"
United States
Anonymous traveller
The price is CA $163
CA $196 total
includes taxes & fees
May 25 - May 26
The Alpine Lodge

Motel 6 Lake George, NY – Adirondacks

Motel 6 Lake George, NY – Adirondacks
2.5 star property
Lake George
9.0 out of 10, Wonderful, (180 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.
"Indoor pool are was real nice as well as game and fitness room. Staff was very accomadating. Will definately stay again. "
United States
Lorraine
The price is CA $93
CA $103 total
includes taxes & fees
Jun 8 - Jun 9
Motel 6 Lake George, NY – Adirondacks
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.

Choose what matters most at beach hotels in Chestertown

Top Chestertown Hotel Reviews

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 Hudson River and Loon Lake.
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.

Explore a world of travel with Expedia