Where to stay around Chestertown?

Our 2018 property listings offer a large selection of 391 vacation rentals near Chestertown. From 200 Houses to 58 Cabins, 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.

What are the popular points of interest near where I can stay when traveling to Chestertown?

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

  • Loon Lake Beach: 479 vacation rentals
  • Lake George Beach: 412 vacation rentals
  • Adirondack Winery: 419 vacation rentals
  • Million Dollar Beach: 406 vacation rentals
  • Dr. Morbid's Haunted House: 413 vacation rentals

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 vacation rentals available near the point of interest of your choice.

Can I rent Houses in Chestertown?

Yes, of course. HomeAway has 200 Houses in Chestertown. Our other popular types of vacation rentals in Chestertown include:

  • Cabins: 58 rentals available
  • Cottages: 40 rentals available
  • Townhouses: 21 rentals available

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

Can I rent golf course rentals in Chestertown?

Absolutely, HomeAway has 289 golf course rentals in Chestertown. You have also many other possibilities in Chestertown area, including:

  • Lake rentals: 178 rentals
  • Mountain rentals: 155 rentals
  • Waterfront rentals: 141 rentals

Please use our search bar to access the selection of vacation rentals.

Can I find a vacation rental with pool in Chestertown?

Yes, you can select your preferred vacation rental with pool among our 47 vacation rentals with pool available in Chestertown. Please use our search bar to access the selection of vacation rentals available.

    The Lakeside Setting of Chestertown is Ready to Explore

    The lake and forests create a pretty picture of Chestertown. This secluded city is known for its coffeehouses, canoeing and horseback riding. Top attractions in the area include Prospect Mountain, Fort William Henry and Lake George Dog Beach. If you're looking for somewhere to stay with more space, consider a vacation rental—many rental homes offer full kitchens and laundry facilities.