Chestertown, NY, USA

Chestertown, NY, USA

We found 368 holiday rentals — enter your dates for availability


Find the best place to stay — Chestertown

Where to stay around Chestertown?

Our 2018 accommodation listings offer a large selection of 368 holiday lettings near Chestertown. From 199 houses to 52 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 travelers, the most popular points of interest to stay near are:

  • Loon Lake Beach: 448 holiday lettings
  • Million Dollar Beach: 389 holiday lettings
  • Water Slide World: 387 holiday lettings
  • Lake George Beach: 396 holiday lettings
  • Oscar Seagle Memorial Theater: 311 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 199 houses in Chestertown. Our other popular types of Chestertown holiday rentals include:

  • Cabins: 52 self catering accommodations
  • Cottages: 29 self catering accommodations
  • Apartments: 16 self catering accommodations

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

Can I find a holiday accommodation with pool in Chestertown?

Yes, you can select your preferred holiday accommodation with pool among our 44 holiday homes with pool available in Chestertown. Please use our search bar to access the selection of holiday rentals available.