Chestertown, MD, USA

Chestertown

We found 71 vacation rentals — enter your dates for availability

Find the best place to stay — Chestertown

3 BR • 1 BA • Sleeps 7
$156 avg/night
4 BR • 3 BA • Sleeps 8
$413 avg/night
2 BR • 1 BA • Sleeps 5
$141 avg/night
Studio • 1 BA • Sleeps 3
$83 avg/night
2 BR • 2 BA • Sleeps 4
$241 avg/night
2 BR • 1 BA • Sleeps 4
$225 avg/night
Search 71 vacation rentals

Search 71 vacation rentals

Where to stay around Chestertown, MD?

Our 2019 property listings offer a large selection of 71 vacation rentals near Chestertown. From 41 Houses to 9 Bungalows, 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.

Can I rent Houses in Chestertown?

Yes, of course. VRBO has 41 Houses in Chestertown. Our other popular types of vacation rentals in Chestertown include:

  • Bungalows: 9 rentals available
  • Cabins: 9 rentals available
  • Cottages: 9 rentals available

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

Can I find a vacation rental with pool in Chestertown?

Yes, you can select your prefered vacation rental with pool among our 13 vacation rentals with pool available in Chestertown. Please use our search bar to access the selection of vacation rentals available.

    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 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)

    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)