Featured Vacation Homes
Welcome to Cape Charles
Nestled on Virginia’s scenic Eastern Shore, Chesapeake Properties invites you to explore our handpicked vacation rentals along the tranquil Chesapeake Bay. From charming beach cottages to spacious family homes, our collection offers the perfect backdrop for a weekend getaway or an extended stay. Whether you’re here to cast a line off the fishing pier, stroll historic streets, or simply unwind by the water, our friendly team is ready to help you find accommodations that feel like home.
Search RentalsWhy Cape Charles & the Chesapeake
If you’re new to vacationing on Virginia’s Eastern Shore, Cape Charles is your gateway to pristine beaches, vibrant small-town charm, and miles of waterfront adventure. This welcoming coastal community sits at the heart of the Chesapeake Bay’s most scenic fishing and boating grounds—and boasts a lively arts scene, locally sourced seafood, and abundant wildlife. Whether you’re seeking sun-soaked relaxation or outdoor exploration, Cape Charles and its Chesapeake Bay surroundings deliver the serenity, scenery, and rich culture that keep guests coming back year after year.
Vacation Rental Management
Our Local Team
Meet the dedicated professionals behind Chesapeake Properties by Portoro
Christina McElroy
Homeowner Success Manager
Christy Iversen
General Manager/Sales