Where to stay around Chestertown, NY?

Our 2018 property listings offer a large selection of 148 vacation rentals near Chestertown. From 65 Houses to 40 Bungalows, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Chestertown for a holiday or a weekend are on VRBO.

What are the popular point of interests near where I can stay when traveling to Chestertown?

VRBO offers a large selection of vacation rentals near lovely places in Chestertown. From VRBO travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Loon Lake Beach: 481 vacation rentals
  • Hiland Golf and Country Club: 388 vacation rentals
  • Around the World Miniature Golf: 417 vacation rentals
  • Dr. Morbid's Haunted House: 419 vacation rentals
  • Pack Demonstration Forest: 501 vacation rentals

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

Can I rent Houses in Chestertown?

Yes, of course. VRBO has 65 Houses in Chestertown. Our other popular types of vacation rentals in Chestertown include:

  • Bungalows: 40 rentals available
  • Cabins: 40 rentals available
  • Cottages: 40 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 prefered vacation rental with pool among our 11 vacation rentals with pool available in Chestertown. Please use our search bar to access the selection of vacation rentals available.

    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 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)

    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)