Where to stay around Chestertown?

Our 2019 property listings offer a large selection of 165 vacation rentals near Chestertown. From 86 Houses to 37 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 HomeAway.

Can I rent Houses in Chestertown?

Yes, of course. HomeAway has 86 Houses in Chestertown. Our other popular types of vacation rentals in Chestertown include:

  • Bungalows: 37 rentals available
  • Cabins: 37 rentals available
  • Cottages: 37 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 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)