Photo by Julie Miller

Search Beach Resorts & Hotels in Chestertown

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check availability on Chestertown Beach Resorts & Hotels

Tonight
21 Jun - 22 Jun
Tomorrow
22 Jun - 23 Jun
Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul

Top Chestertown Beach Resorts & Hotels

Pine Tree Motel & Cabins
Exterior

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (126)
"I would definitely stay here again."
The price is 1.258 kr.
includes taxes & fees
25 Jun - 26 Jun
Pine Tree Motel & Cabins
Sleepy Hollow, Pool/AC/Fireplace,Cabin Steps to Loon Lake
Property grounds

Sleepy Hollow, Pool/AC/Fireplace,Cabin Steps to Loon Lake

9.8 out of 10, Exceptional, (6)
"Our grandkids can’t stop talking about our stay in the Sleepy Hollow cabin. They loved the pool and Loon lake. The evenings around the fire pit were great! A special thanks to Wendy for her hospitality and to Anthony for bringing the marshmallows!"
The price is 2.955 kr.
includes taxes & fees
6 Jul - 7 Jul
Sleepy Hollow, Pool/AC/Fireplace,Cabin Steps to Loon Lake
Silver Bay YMCA Inn and Conference Center
Private beach, beach volleyball

Silver Bay YMCA Inn and Conference Center

3.0 star property
8.4 out of 10, Very good, (89)
"Nice , serene place with a lot of attractions within the property . I really liked the place and my family as well "
The price is 1.157 kr.
includes taxes & fees
22 Jun - 23 Jun
Silver Bay YMCA Inn and Conference Center
Trout House Village Resort
Luxury Cabin, 1 Bedroom, Lake View | Living area | 42-inch Smart TV with digital channels, DVD player, streaming services

Trout House Village Resort

3.0 star property
10.0 out of 10, Exceptional, (11)
"Absolutely wonderful place and super friendly staff "
The price is 1.783 kr.
includes taxes & fees
26 Jun - 27 Jun
Trout House Village Resort
Baymont by Wyndham Queensbury / Lake George
Hypo-allergenic bedding, in-room safe, desk, blackout curtains

Baymont by Wyndham Queensbury / Lake George

2.5 star property
7.4 out of 10, Good, (1003)
"Quick check in and very friendly!"
The price is 576 kr.
includes taxes & fees
22 Jun - 23 Jun
Baymont by Wyndham Queensbury / Lake George
Country Inn & Suites by Radisson, Lake George (Queensbury), NY
Room, 2 Queen Beds, Non Smoking | 1 bedroom, premium bedding, pillow-top beds, individually decorated

Country Inn & Suites by Radisson, Lake George (Queensbury), NY

3.0 star property
9.0 out of 10, Wonderful, (1141)
"Excellent location "
The price is 879 kr.
includes taxes & fees
23 Jun - 24 Jun
Country Inn & Suites by Radisson, Lake George (Queensbury), NY
Mohican Resort Motel
Gazebo

Mohican Resort Motel

2.5 star property
9.0 out of 10, Wonderful, (137)
"Super sweet staff, CLEAN room, easy parking and great pool area. So dog friendly, will definitely return and recommend! "
The price is 615 kr.
includes taxes & fees
25 Jun - 26 Jun
Mohican Resort Motel
Studio Motel
Fountain

Studio Motel

2.0 star property
8.6 out of 10, Excellent, (902)
"The queen room was a little small. For the price it was adequate. Good location. "
The price is 586 kr.
includes taxes & fees
24 Jun - 25 Jun
Studio Motel
The Juliana Resort
Terrace/patio

The Juliana Resort

2.5 star property
8.8 out of 10, Excellent, (158)
"Beautiful property! Lake view was amazing. "
The price is 785 kr.
includes taxes & fees
22 Jun - 23 Jun
The Juliana Resort
Depe Dene Lakeside Resort
Lakefront Two Queen Efficiency | 2 bedrooms, hypo-allergenic bedding, individually decorated

Depe Dene Lakeside Resort

2.0 star property
8.8 out of 10, Excellent, (289)
"Beautiful property "
Depe Dene Lakeside Resort
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.

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.
How many beach hotels should I expect to find in Chestertown?
Choose from one of Expedia's 25 hotels in Chestertown for your beachside break.
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 Rogers 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.