Chester, MD, USA Vacation Rentals

Discover popular destinations in and around Chester

Chesapeake Bay
1,136 vacation rentals
Eastern Shore
3,362 vacation rentals
Kent Island
564 vacation rentals
Chesapeake Bay Bridge
497 vacation rentals
Annapolis
505 vacation rentals
Chestertown
71 vacation rentals
Tilghman Island
291 vacation rentals
Stevensville
524 vacation rentals
Rock Hall
401 vacation rentals
Oxford
190 vacation rentals
Saint Michaels
337 vacation rentals
4, Kent Island
564 vacation rentals
Severna Park
619 vacation rentals
Maryland Quiet Waters Park
525 vacation rentals
Pasadena
621 vacation rentals
Centreville
109 vacation rentals
Sandy Point State Park
486 vacation rentals
Southern Maryland
145 vacation rentals

Explore a selection of Chester vacation rentals