Chestertown, MD, USA

Chestertown, MD, USA

We found 51 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 51 holiday lettings near Chestertown. From 33 houses to 5 cottages, 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:

  • Garfield Center for the Arts at the Prince Theater: 75 holiday lettings
  • Washington College: 72 holiday lettings
  • Historical Society of Kent County Maryland: 76 holiday lettings
  • Wilmer Park: 77 holiday lettings
  • Elk Neck State Park: 53 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 33 houses in Chestertown. Our other popular types of Chestertown holiday rentals include:

  • Cottages: 5 self catering accommodations
  • Apartments: 4 self catering accommodations

Can I find a holiday accommodation with pool in Chestertown?

Yes, you can select your preferred holiday accommodation with pool among our 11 holiday homes with pool available in Chestertown. Please use our search bar to access the selection of holiday rentals available.