Chestertown holiday rentals
Find spaces that suit your style
Find the best place to stay - Chestertown
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
- 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, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Why people love visiting cosy Chestertown
Take a holiday 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 holiday rentals feature full kitchens and laundry facilities.
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 experience everything that makes Chestertown a one-of-a-kind holiday spot. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:
- 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 looking for fun outdoor activities or just want to appreciate the scenery, Chestertown is a great place to get out in nature. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:
- 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)
Transport 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 centre. If you can't find a flight that works for your travel itinerary, you could also fly into Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away.