Chestertown, MD, USA

Chestertown, MD, USA

We found 53 vacation rentals — enter your dates for availability


Find the best place to stay — Chestertown

Where to stay around Chestertown, MD?

Our 2018 property listings offer a large selection of 53 vacation rentals near Chestertown. From 33 houses to 5 apartments, 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.

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 5 most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Washington College: 77 vacation rentals
  • Historical Society of Kent County Maryland: 81 vacation rentals
  • Garfield Center for the Arts at the Prince Theater: 81 vacation rentals
  • Wilmer Park: 82 vacation rentals
  • Aberdeen Proving Ground: 50 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 houses in Chestertown?

Yes, of course. VRBO has 33 houses in Chestertown. Our other popular types of vacation rentals in Chestertown include:

  • Apartments: 5 rentals available
  • Cottages: 5 rentals available
  • Estates: 4 rentals available

Can I rent beachfront rentals in Chestertown?

Absolutely, VRBO has 19 beachfront rentals in Chestertown. You have also many other possibilities in Chestertown area, including:

  • Golf rental rentals: 17 rentals

Please use our search bar to access the selection of vacation rentals.

Can I find a vacation rental with online bookable in Chestertown?

Yes, you can select your prefered vacation rental with online bookable among our 53 vacation rentals with online bookable available in Chestertown. Please use our search bar to access the selection of vacation rentals available.