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
20 Jul - 21 Jul
Tomorrow
21 Jul - 22 Jul
Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug

Top Chestertown Beach Resorts & Hotels

Pine Tree Motel & Cabins
Exterior

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (129)
"Excellent location and staff was very friendly."
The price is Rp2.851.975
Rp3.165.692 total
includes taxes & fees
21 Jul - 22 Jul
Pine Tree Motel & Cabins
Friends Lake Inn
Premier Room | 1 bedroom, premium bedding, individually decorated

Friends Lake Inn

4.0 star property
8.8 out of 10, Excellent, (90)
"Quiet lodging and friendly staff"
The price is Rp3.634.557
Rp4.034.322 total
includes taxes & fees
21 Jul - 22 Jul
Friends Lake Inn
The Fern Lodge
Lake view

The Fern Lodge

3.5 star property
9.8 out of 10, Exceptional, (46)
"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
Chestertown Hideaway w/ Lake & Beach Access!
House (3 Bedrooms) | Interior

Chestertown Hideaway w/ Lake & Beach Access!

3.0 star property
Chestertown Hideaway w/ Lake & Beach Access!
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.
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 .
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 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.