Find Cheap Hotels in Chestertown, NY

  • 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 Cheap Hotels

Our top choices for Chestertown cheap hotels

Friends Lake Inn

Friends Lake Inn
4.0 star property
Chestertown
8.6 out of 10, Excellent, (102 reviews)
"Friendly staff, room was clean, well maintained. Ate at the restaurant, food was great. "
United States
Erin
The price is NT$6,991
NT$7,760 total
includes taxes & fees
Feb 19 - Feb 20
Friends Lake Inn

The Fern Lodge

The Fern Lodge
3.5 star property
Chestertown
10.0 out of 10, Exceptional, (52 reviews)
"I cannot say enough good things about the Fern Lodge. Beautiful atmosphere, wonderful host. Will be returning! "
United States
Morgan
The Fern Lodge
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

Frequently asked questions

What is Chestertown like for travelers on a budget?
Discover discount places to stay in Chestertown on Expedia.com and plan a trip that fits your budget. Chestertown is a destination that visitors enjoy for its lake views. You can browse a variety of hotels and other accommodations with Member Prices to score the best deal for you. Guided by our site's helpful page filters, you can search by your price range, or by favorite amenities like free parking and free breakfast. Or, try refining your search with the location filters to see affordable options around local attractions, such as Loon Lake Beach or Friends Lake. While you browse, use the heart button to save your favorites so that you can come back to them when you're ready to book. Need a flight or a rental car along with your hotel? Choose from the vacation packages available under Bundle and Save and discover huge discounts by booking transportation at the same time.
When is the best time for a budget trip to Chestertown?
Weather is probably a major factor when you plan your trip to Chestertown, and keep in mind that cheaper options are usually available when the weather isn't as good. 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 in Chestertown?
Chestertown is known for its lake views and offers things to see and do without spending a fortune. You can budget for the local attractions that interest you most, and then fill your itinerary with activities that cost little or nothing at all. Enjoy the outdoors at Loon Lake Beach and Friends Lake, or check out the area's cultural spots like The Sembrich.
How can I get to Chestertown and get around on a budget?
Scoping out the transportation options in Chestertown is a smart way to keep your trip affordable. The closest airport is Glens Falls, NY (GFL-Floyd Bennett Memorial), situated 23.6 mi (38 km) away. Chestertown might not have very many public transportation choices so a car rental could be an economical alternative to see more of the area.

Explore a world of travel with Expedia