Find the best place to stay — Chestertown

Where to stay around Chestertown?

Our 2018 property listings offer a large selection of 57 vacation rentals near Chestertown. From 35 houses to 5 apartments, 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 35 houses in Chestertown. Our other popular types of vacation rentals in Chestertown include:

  • Apartments: 5 rentals available
  • Cottages: 5 rentals available
  • Estates: 4 rentals available

Can I rent golf rentals in Chestertown?

Absolutely, HomeAway has 20 golf rentals in Chestertown. You have also many other possibilities in Chestertown area, including:

  • Waterfront rentals: 19 rentals
  • Downtown rentals: 7 rentals
  • Beach rentals: 2 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 11 vacation rentals with pool available in Chestertown. Please use our search bar to access the selection of vacation rentals available.

    Festive Chestertown Will Entice You

    Enjoy the area's culture, history and sports with a vacation home for rent in Chestertown. This city's university setting, festivals and boating attract many visitors, as does its quaint and family-friendly location. Need more space to accommodate a family vacation, friends trip or 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 like 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.