Discover a selection of 72 vacation rentals in Chestertown, MD 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 kitchens. Prices start at $169 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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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, 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

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, MD?

Our 2020 property listings offer a large selection of 72 vacation rentals around Chestertown. From 9 condo and apartment rentals to 45 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What is the best area to stay when traveling to Chestertown?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Chestertown:

  • Historic District: 71 vacation rentals
  • Eastport: 96 vacation rentals
  • Homewood: 36 vacation rentals
  • Murray Hill: 66 vacation rentals
  • West Annapolis: 18 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Chestertown?

Vrbo offers a large selection of vacation rentals near lovely places in Chestertown. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Historical Society of Kent County Maryland: 75 vacation rentals
  • Garfield Center for the Arts at the Prince Theater: 76 vacation rentals
  • Washington College: 73 vacation rentals
  • Rolphs Wharf Marina: 75 vacation rentals
  • Wilmer Park: 74 vacation rentals

But there are many other points of interest around Chestertown listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Condos/Apartments in Chestertown?

Yes, of course. Vrbo has 9 Condos/Apartments in Chestertown. Our other popular types of vacation rentals in Chestertown include:

  • Houses: 45 rentals available
  • Cottages: 13 rentals available
  • Studios: 6 rentals available

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

Can I find a vacation rental with pool in Chestertown?

Yes, you can select your preferred vacation rental with pool among our 17 vacation rentals with pool available in Chestertown. Please use our search bar to access the selection of vacation rentals available.

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