Chestertown vacation rentals
Find spaces that suit your style
Find the best place to stay - Chestertown
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Top rated rentals - Chestertown
Amazing Property
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value
Why people love visiting cozy Chestertown
Take a vacation to Chestertown and enjoy the area's festivals, history and art galleries. This city's sporting events, university setting and boating draw many visitors. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.
Activities and attractions in Chestertown
Do you want to find top things to see and do while you're in the area? Venture out of your vacation home and experience everything that makes Chestertown a one-of-a-kind vacation spot. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:
- Queenstown Harbor Golf Club (16.7 mi / 26.9 km)
- Queenstown Harbor Golf Links (16.7 mi / 26.9 km)
- Bay Hills Golf Club (25 mi / 40.2 km)
- Cassinelli Winery and Vineyards (7.1 mi / 11.3 km)
- Crumpton Auction (8.4 mi / 13.5 km)
- Crow Farm and Vineyard (10.2 mi / 16.4 km)
Exploring the natural landscape of Chestertown
Whether you're an adventurous traveler or just want to spend some time taking in the scenery, Chestertown is a great place to spend some time outside. Here are some of the area’s noteworthy sights, all within 30 miles (48.2 km) of the city center:
- Betterton Beach (10.5 mi / 16.9 km)
- Miami Beach (17.2 mi / 27.7 km)
- Gunpowder Falls State Park (17.9 mi / 28.9 km)
- Elk Neck State Park (18.6 mi / 29.9 km)
- Sandy Point Beach (22.6 mi / 36.4 km)
- Sandy Point State Park (22.7 mi / 36.5 km)
Transportation options to and around Chestertown
The nearest airport is in Baltimore, MD (MTN-Martin State), located 20.3 mi (32.7 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away.