Destination guide

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

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)
Natural highlights

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)
How to get there

Transport to and around Chestertown

The nearest airport is in Baltimore, MD (MTN-Martin State), located 19.5 mi (31.4 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Easton, MD (ESN-Easton - Newnam), which is 27.3 mi (43.9 km) away.

How many holiday accommodation are available around Chestertown?

Our 2019 accommodation listings offer a large selection of 74 holiday rentals around Chestertown. From 42 Houses to 12 Cottages, find unique holiday homes for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Chestertown is on Stayz.

What is the best area to stay when travelling to Chestertown?

Whether you are travelling solo or with family and friends, here are the areas with the largest selection of holiday rentals for a long holiday or just a weekend break in Chestertown:

  • Eastport: 156 holiday homes
  • Homewood: 61 holiday homes
  • Historic District: 102 holiday homes
  • Hillsmere: 18 holiday homes
  • Epping Forest: 20 holiday homes

For other neighbourhoods, please use our search bar to access the selection of holiday homes available.

What are the most popular points of interest and landmarks to stay near when travelling to Chestertown?

Stayz offers a large selection of holiday homes near great places in Chestertown. From Stayz travellers, the most popular points of interest to stay near are:

  • Wilmer Park: 82 holiday rentals
  • River Arts Chestertown: 81 holiday rentals
  • Historical Society of Kent County Maryland: 82 holiday rentals
  • Garfield Center for the Arts at the Prince Theater: 82 holiday rentals
  • Washington College: 78 holiday rentals

But there are many other points of interest around Chestertown listed on Stayz 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. Stayz offers 42 Houses in Chestertown. Our other popular types of Chestertown holiday rentals include:

  • Cottages: 12 holiday houses
  • Cabins: 12 holiday houses
  • Bungalows: 12 holiday houses

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

Can I find a holiday accommodation with pool in Chestertown?

Yes, you can select your preferred holiday accommodation with pool among our 15 holiday homes with pool available in Chestertown. Please use our search bar to access the selection of holiday rentals available.