Skip to main content.

Hotels in Chestertown, New York

Search & Compare Chestertown Hotels

Save more with Secret Prices

Get instant savings with Secret Prices

  • Pay now or later on most rooms
  • Free cancellation on most rooms
  • Price Guarantee

Best hotels in Chestertown

What's Chestertown like?

If you're looking for a place to get away, look no further than Chestertown. Whether you're planning to stay for a night or for the week, the area around Chestertown has accommodations to fit every need. Search for hotels in Chestertown with by checking our online map. Our map displays the areas and neighborhoods around all Chestertown hotels so you can see how close you are from landmarks and attractions, and then refine your search within the larger area. The best Chestertown hotel deals are here with our lowest price guarantee.

Where are the best places to stay in Chestertown?

Top hotel picks in and around Chestertown:

The Fern Lodge

3.5-star beach B&B with bar/lounge, near Friends Lake
  • • Free breakfast • Free parking • Free WiFi • 8 spa tubs • Fitness center

Friends Lake Inn

Chestertown ski-in/ski-out hotel with ski storage, ski rentals
  • • Free parking • Free WiFi • Restaurant • Sauna • Comfy beds

Pine Tree Motel & Cabins

Mountain motel
  • • Free parking • Free WiFi • Terrace • 24-hour front desk • Central location

Loon Lake Retreat With Private Dock

Chestertown mountain apartment with kitchen
  • • Free in-room WiFi • Central location

What types of hotels are available in Chestertown?

We have 41 Chestertown accommodations with prices starting at USD 46. Choose one of our 71 deals and get discounts of up to 30%.

Below are the number of accommodations by star rating in Chestertown and the surrounding area:

  • • 14 4-star accommodations from USD 88 per night
  • • 65 3-star accommodations from USD 67 per night
  • • 39 2-star accommodations from USD 51 per night

How to Get to Chestertown

What is the closest airport to Chestertown?

  • • Glens Falls, NY (GFL-Floyd Bennett Memorial), 23 mi (37 km) from central Chestertown

Things to See and Do in Chestertown

What is there to see in Chestertown?

  • • Friends Lake
  • • Loon Lake Beach
  • • Tripp Pond
  • • Loon Lake

What is there to do near Chestertown:

  • • Pack Demonstration Forest (5.5 mi/8.9 km from the city center)
  • • Tannery Pond Community Center (9.2 mi/14.7 km from the city center)

When is the best time to visit Chestertown?

  • • Hottest months: July, August, June, September (average 79°F)
  • • Coldest months: January, February, December, March (average 9°F)
  • • Rainiest months: July, August, May, and June (average 3.73 inches of rainfall)