Destination guide

The cozy city of Chestertown awaits you

Enjoy the area's festivals, history and art galleries and make a vacation rental your home during your stay in Chestertown. This city's sporting events, university setting and boating draw many visitors. Whether you're planning a family vacation, friends trip or romantic retreat, HomeAway has a great selection of vacation 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 cozy vacation 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 center:

  • 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 features

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 vacation in Chestertown. These are some of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

  • 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

Transportation to and around Chestertown

The nearest airport is in Baltimore, MD (MTN-Martin State), located 19.5 mi (31.4 km) from the city center. 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.

Where to stay around Chestertown?

Our 2019 property listings offer a large selection of 75 vacation rentals near Chestertown. From 44 Houses to 12 Cottages, 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.

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

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Chestertown:

  • Eastport: 149 vacation rentals
  • Historic District: 103 vacation rentals
  • Naval Academy: 106 vacation rentals
  • Hillsmere: 18 vacation rentals
  • Epping Forest: 20 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when traveling to Chestertown?

HomeAway offers a large selection of vacation rentals near lovely places in Chestertown. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Washington College: 80 vacation rentals
  • Garfield Center for the Arts at the Prince Theater: 84 vacation rentals
  • Wilmer Park: 84 vacation rentals
  • Rolphs Wharf Marina: 82 vacation rentals
  • Historical Society of Kent County Maryland: 84 vacation rentals

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 vacation rentals available near the point of interest of your choice.

Can I rent Houses in Chestertown?

Yes, of course. HomeAway has 44 Houses in Chestertown. Our other popular types of vacation rentals in Chestertown include:

  • Cottages: 12 rentals available
  • Cabins: 12 rentals available
  • Bungalows: 12 rentals available

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

Can I find a vacation rental with pool in Chestertown?

Yes, you can select your preferred vacation rental with pool among our 14 vacation rentals with pool available in Chestertown. Please use our search bar to access the selection of vacation rentals available.

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