Find the best place to stay — Chestertown

Where to stay around Chestertown, MD?

Our 2018 property listings offer a large selection of 57 vacation rentals near Chestertown. From 37 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.

Can I rent houses in Chestertown?

Yes, of course. VRBO has 37 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 golf rental rentals in Chestertown?

Absolutely, VRBO has 20 golf rental rentals in Chestertown. You have also many other possibilities in Chestertown area, including:

  • Beachfront rentals: 19 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 57 vacation rentals with online bookable available in Chestertown. Please use our search bar to access the selection of vacation rentals available.