Discover a selection of 221 vacation rentals in Chestertown, NY that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $104 per night, and houses and cabins are popular options for a stay in Chestertown. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Chestertown
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Destination guide

The remote area of Chestertown awaits your stay

The lake and forests provide a pleasant backdrop to your vacation home in Chestertown. This relaxing city is known for its coffeehouses, canoeing and horseback riding. Prospect Mountain and Fort William Henry are just a couple of the must-sees in the area. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities

Activities and attractions in and around Chestertown

Do you want to discover attractions to visit while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Chestertown has to offer. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Pack Demonstration Forest (5.9 mi / 9.4 km)
  • Gore Mountain Ski Resort (9.3 mi / 14.9 km)
  • Hickory Ski Center (11.1 mi / 17.9 km)
  • Adirondack Winery (15.7 mi / 25.3 km)
  • Top of the World Golf Course (16.5 mi / 26.6 km)
  • Water Slide World (16.9 mi / 27.1 km)
Natural features

Exploring the natural features in Chestertown

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Chestertown is a great place to get outside. These are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Prospect Mountain (15.2 mi / 24.5 km)
  • Lake George Dog Beach (16.3 mi / 26.2 km)
  • Loon Lake Beach (1.8 mi / 2.9 km)
  • Pack Demonstration Forest (5.9 mi / 9.4 km)
  • Natural Stone Bridge and Caves (7.7 mi / 12.3 km)
  • North Creek Ski Bowl Town Park (9 mi / 14.6 km)
How to get there

How to get to and around Chestertown

Fly into Glens Falls, NY (GFL-Floyd Bennett Memorial), the closest airport, located 23.3 mi (37.5 km) from the city center.

How many vacation rentals are available around Chestertown, NY?

Our 2021 property listings offer a large selection of 221 vacation rentals around Chestertown. From 204 house rentals to 49 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses in Chestertown?

Yes, of course. Vrbo has 204 Houses in Chestertown. Our other popular types of vacation rentals in Chestertown include:

  • Cabins: 49 rentals available
  • Cottages: 41 rentals available
  • Bungalows: 41 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments and more.

Can I find a vacation rental with pool in Chestertown?

Yes, you can select your preferred vacation rental with pool among our 55 vacation rentals with pool available in Chestertown. Please use our search bar to access the selection of vacation rentals available.