Where to stay near Chestertown?

Our 2020 accommodation listings offer a large selection of 71 holiday rentals near Chestertown. From 9 Condos/Apartments to 44 Houses, find unique holiday homes for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay near Chestertown is on HomeAway.

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

Whether you are travelling solo or with family and friends, here are the areas with the largest selection of holiday rentals for a long holiday or just a weekend break in Chestertown:

  • Homewood: 37 holiday homes
  • Eastport: 97 holiday homes
  • Historic District: 72 holiday homes
  • West Annapolis: 18 holiday homes
  • Murray Hill: 67 holiday homes

For other neighbourhoods, please use our search bar to access the selection of holiday homes available.

What are the most popular points of interest and landmarks to stay near when travelling to Chestertown? offers a large selection of holiday homes near great places in Chestertown. From travellers, the most popular points of interest to stay near are:

  • Garfield Center for the Arts at the Prince Theater: 74 holiday rentals
  • Rolphs Wharf Marina: 73 holiday rentals
  • Wilmer Park: 73 holiday rentals
  • Historical Society of Kent County Maryland: 74 holiday rentals
  • River Arts Chestertown: 75 holiday rentals

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

Can I rent Condos/Apartments in Chestertown?

Yes, of course. offers 9 Condos/Apartments in Chestertown. Our other popular types of Chestertown holiday rentals include:

  • Houses: 44 holiday houses
  • Cottages: 13 holiday houses
  • Studios: 6 holiday houses

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

Can I find a holiday accommodation with pool in Chestertown?

Yes, you can select your preferred holiday accommodation with pool among our 16 holiday homes with pool available in Chestertown. Please use our search bar to access the selection of holiday rentals available.