Where to stay around Chestertown?

Our 2018 accommodation listings offer a large selection of 49 holiday lettings near Chestertown. From 31 houses to 5 apartments, 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 travellers, the most popular points of interest to stay near are:

  • Garfield Center for the Arts at the Prince Theater: 43 holiday lettings
  • Washington College: 73 holiday lettings
  • Historical Society of Kent County Maryland: 46 holiday lettings
  • Wilmer Park: 79 holiday lettings
  • Elk Neck State Park: 43 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 31 houses in Chestertown. Our other popular types of Chestertown holiday rentals include:

  • Apartments: 5 self catering accommodations
  • Cottages: 5 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 9 holiday homes with pool available in Chestertown. Please use our search bar to access the selection of holiday rentals available.

    Music fest Chestertown will entice you

    Enjoy the area's culture, historical sites and sports with a rental holiday home in Chestertown. This city's universities, festivals and boating attract many visitors, as does its cosy and family-friendly location. Need more space to accommodate a family holiday, a trip with friends or a romantic retreat? Rental homes often come with a full kitchen, separate dining area and laundry facilities.

    Attractions in and around Chestertown

    Looking for places to see while you're in Chestertown? Don't miss cultural highlights such as Garfield Center for the Arts at the Prince Theater and Historical Society of Kent County Maryland. To appreciate the outdoor scene, make time for green spaces such as Elk Neck State Park. If you have extra time, you might want to explore the campus of Washington College. Activities around the area include Rolphs Wharf Marina, Cassinelli Winery and Vineyards and Rock Hall Harbor. You may also want to visit Wilmer Park, The Mainstay or Ferry Park.