Find Cheap Hotels in Chestertown, NY

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.

Based on reviews, Pine Tree Motel & Cabins is a popular 2-star property for our travelers looking for an economical choice, and features free WiFi and free parking.

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.

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 Strand Theater.

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.