Destination guide

The secluded area of Chestertown awaits your stay

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


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 holiday 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 centre:

  • 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 centre:

  • 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 centre.

How many holiday rentals are available around Chestertown?

Our 2020 accommodation listings offer a large selection of 204 holiday lettings around Chestertown. From 93 houses to 44 cabins, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

What are the most popular points of interest and landmarks to stay near when travelling to Chestertown? offers a large selection of holiday accommodations near great places in Chestertown. From travellers, the most popular points of interest to stay near are:

  • Loon Lake Beach: 585 holiday lettings
  • Magic Forest Park: 523 holiday lettings
  • Around the World Miniature Golf: 549 holiday lettings
  • Dr. Morbid's Haunted House: 547 holiday lettings
  • West Mountain Ski Resort: 719 holiday lettings

But there are many other points of interest around Chestertown listed on 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. offers 93 Houses in Chestertown. Our other popular types of Chestertown holiday rentals include:

  • Cabins: 44 self catering accommodations
  • Cottages: 44 self catering accommodations
  • Flats: 9 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 51 holiday homes with pool available in Chestertown. Please use our search bar to access the selection of holiday rentals available.

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