Discover a selection of 83 vacation rentals in Chestertown that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $111 per night, and condos and houses are popular options for a stay in Chestertown. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Chestertown
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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, Vrbo 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.

How many vacation rentals are available around Chestertown?

Our 2021 property listings offer a large selection of 83 vacation rentals around Chestertown. From 7 condo and apartment rentals to 71 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.