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 highlights

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)
Transport

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.

Where to stay around Chestertown?

Our 2019 accommodation listings offer a large selection of 173 holiday lettings near Chestertown. From 90 Houses to 39 Cabins, find unique self catering accommodation for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay near Chestertown is on HomeAway.

What are the most popular points of interest and landmarks to stay near when travelling to Chestertown?

HomeAway offers a large selection of holiday accommodations near great places in Chestertown. From HomeAway travellers, the most popular points of interest to stay near are:

  • Loon Lake Beach: 562 holiday lettings
  • Top of the World Golf Course: 470 holiday lettings
  • Hickory Ski Center: 554 holiday lettings
  • Sunnyside Par 3 Golf Course: 432 holiday lettings
  • Lake George Shoreline Cruises: 499 holiday lettings

But there are many other points of interest around Chestertown listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of holiday rentals available near the point of interest of your choice.

Can I rent Houses in Chestertown?

Yes, of course. HomeAway offers 90 Houses in Chestertown. Our other popular types of Chestertown holiday rentals include:

  • Cabins: 39 self catering accommodations
  • Cottages: 39 self catering accommodations
  • Condos/Apartments: 14 self catering accommodations

But you can also enjoy a great stay in one of our other holiday rentals including Bungalows and more.

Can I find a holiday accommodation with pool in Chestertown?

Yes, you can select your preferred holiday accommodation with pool among our 12 holiday homes with pool available in Chestertown. Please use our search bar to access the selection of holiday rentals available.

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