Discover a selection of 84 holiday rentals in Chestertown that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and private pool. Prices start at £ 104 per night, and flats & apartments 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 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, Vrbo 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 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 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.

Can I find a vacation rental around Chestertown?

Yes, our 2021 property listings offer a large selection of 84 vacation rentals near Chestertown. From 7 flats & apartments to 72 houses, 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 Vrbo.