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Can I find a vacation rental around Chestertown?

Yes, our 2020 property listings offer a large selection of 71 vacation rentals near Chestertown. From 9 Condos/Apartments to 44 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 HomeAway.

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: 72 vacation rentals
  • Eastport: 97 vacation rentals
  • Homewood: 37 vacation rentals
  • Murray Hill: 67 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 points of interest near where I can stay when traveling to Chestertown?

HomeAway.com offers a large selection of vacation rentals near lovely places in Chestertown. From HomeAway.com travelers, the 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: 75 vacation rentals
  • Washington College: 72 vacation rentals
  • Rolphs Wharf Marina: 73 vacation rentals
  • Wilmer Park: 73 vacation rentals

But there are many other points of interest around Chestertown listed on HomeAway.com 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. HomeAway.com has 9 Condos/Apartments in Chestertown. Our other popular types of vacation rentals in Chestertown include:

  • Houses: 44 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 16 vacation rentals with pool available in Chestertown. Please use our search bar to access the selection of vacation rentals available.

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