Photo by Julie Miller

Chestertown Hotel Guide - Beach Hotels in Chestertown, New York

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Check availability on Chestertown Beach Hotels

Top Chestertown Beach Hotels

Pine Tree Motel & Cabins
Exterior

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (135)
"Excellent location and staff was very friendly."
The price is €166
includes taxes & fees
26 Aug - 27 Aug
Pine Tree Motel & Cabins
Friends Lake Inn
Premier Room

Friends Lake Inn

4.0 star property
8.8 out of 10, Excellent, (97)
"Beautiful setting. Very clean. Charming building. Friendly staff. Breakfast included."
The price is €212
includes taxes & fees
20 Aug - 21 Aug
Friends Lake Inn
The Fern Lodge
Lake view

The Fern Lodge

3.5 star property
9.8 out of 10, Exceptional, (47)
"We had such a great experience the first night so we moved our plans and stayed a second, next time we will definitely stay even longer."
The Fern Lodge
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
Sun-loungers

Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing

10.0 out of 10, Exceptional, (34)
"Great location, very responsive host. Property was well cared for, large yard, large bedrooms. The downstairs suite was perfect for adult offspring. Walkout to hot tub, fire pit, yard games if you have them. Probably the best vrbo ever."
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Fridge, microwave, oven, stovetop

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

10.0 out of 10, Exceptional, (67)
"My family and i had a great time here! The place is Amazing and we would definitely stay again! "
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
On the beach

#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!

9.6 out of 10, Exceptional, (16)
"The views were absolutely amazing! We will definitely be back."
#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
Peaceful Lakeside Retreat with Private Beach
Beach nearby, sun-loungers, beach towels

Peaceful Lakeside Retreat with Private Beach

9.2 out of 10, Wonderful, (21)
"The area was quiet and house was nice. Perfect for our needs."
Peaceful Lakeside Retreat with Private Beach
Elizabeth. A Guest House Near Lake George.
Lake

Elizabeth. A Guest House Near Lake George.

8.2 out of 10, Very good, (45)
"It is an older house with a lot of character. For our very large family. The pool was super clean and a hit with everyone. Very convenient to lake George, and having a grocery store a very short walk away was a huge bonus!"
Elizabeth. A Guest House Near Lake George.
Lakefront cabin with beautiful loft, game room, views, private dock
Exterior

Lakefront cabin with beautiful loft, game room, views, private dock

9.2 out of 10, Wonderful, (42)
"Great little family getaway "
Lakefront cabin with beautiful loft, game room, views, private dock
Eagles Nest at Loon Lake near Gore Mountain
Exterior

Eagles Nest at Loon Lake near Gore Mountain

10.0 out of 10, Exceptional, (111)
"A fantastic location for those looking to get away in the Adirondacks. Conveniently close to Chestertown, as well as many outdoor activities, Eagles Nest was an awesome location to stay at with friends and family. "
Eagles Nest at Loon Lake near Gore Mountain
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.

Top Chestertown Hotel Reviews

Lakefront Terrace Resort

Lakefront Terrace Resort

10/10 Excellent
"We go every year we enjoy ☀️"
Jessica 2-night trip
Posted 2 days ago
Lakefront Terrace Resort

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 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 such as 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 centre. If you'd like to venture out around the area, you may want a rental car for your journey.