Where to stay around Chestertown?

Our 2018 accommodation listings offer a large selection of 51 holiday lettings near Chestertown. From 32 Houses to 6 Condos/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: 77 holiday lettings
  • Washington College: 73 holiday lettings
  • Historical Society of Kent County Maryland: 77 holiday lettings
  • Wilmer Park: 79 holiday lettings
  • Elk Neck State Park: 48 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 32 Houses in Chestertown. Our other popular types of Chestertown holiday rentals include:

  • Condos/Apartments: 6 self catering accommodations
  • Bungalows: 5 self catering accommodations
  • Cabins: 5 self catering accommodations

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

Can I rent waterfront rentals in Chestertown?

Absolutely, HomeAway has 19 waterfront rentals in Chestertown. You have also many other possibilities in Chestertown area, including:

  • Village rentals: 8 holiday rentals
  • Downtown rentals: 7 holiday rentals
  • Rural rentals: 7 holiday rentals

Please use our search bar to access the selection of holiday lettings.

Can I find a holiday accommodation with private pool in Chestertown?

Yes, you can select your preferred holiday accommodation with private pool among our 5 holiday homes with private pool available in Chestertown. Please use our search bar to access the selection of holiday rentals available.

    The cosy city of Chestertown awaits you

    Enjoy the area's festivals, history and art galleries with a rental holiday home in Chestertown. This city's sporting events, university setting and boating draw many visitors. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

    Activities and attractions in Chestertown

    Do you want to discover top things to see and do while you're in town? Venture out of your cosy holiday rental and check out everything that Chestertown has to offer. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

    • Cassinelli Winery and Vineyards (7.1 mi / 11.5 km)
    • Tilmon's Island Winery (12.4 mi / 20 km)
    • Queenstown Harbor Golf Club (15.4 mi / 24.8 km)
    • Rocky Point Golf Course (17.4 mi / 28.1 km)

    Exploring the natural landscape of Chestertown

    Whether you're looking for exciting outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Chestertown. These are some of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

    • Wilmer Park (1.4 mi / 2.3 km)
    • Ferry Park (9.9 mi / 15.9 km)
    • Adkins Arboretum (19.4 mi / 31.2 km)
    • Elk Neck State Park (19.8 mi / 31.9 km)
    • Sandy Point State Park (21.1 mi / 33.9 km)
    • Kent Island (21.6 mi / 34.8 km)