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Vacation rentals in Cape Charles

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Top-rated vacation rentals in Cape Charles

Guests agree: these stays are highly rated for location, cleanliness, and more.

Hotel room in Cape Charles
The Laughing King Retreat, Honeymoon Island Suite
The Laughing King Retreat is an adults only, organic waterfront farm situated directly on the peaceful waters of the Chesapeake Bay. Your private guest suite will enjoy breathtaking sunrises and sunsets, private waterfront pool, private beach, hiking trails, miles of soft sugar sand sandbars to explore and enjoy. Private Chesapeake Bay water access for boating, swimming, paddle boarding, fishing or just soaking. For a complete list of all the retreat rooms click the photo of me and Suzanne.
$170 per night
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Home in Cape Charles
Experience Tiny Living, in Cape Charles, Va
Step back in time when you stay at this unique and historic tiny home named "Milk". Formally known as the ESSO Auto Park in the 1930's. Our Historic Tiny Homes are Conveniently located just a short 3 min drive to downtown Cape Charles and our Beautiful Beach. Giving you easy access to all that our town of Cape Charles has to offer. From Our Beach, Restaurants, Shops, Music, Events,...... and more....... Charter boats tours , kayaking , walking trails, we are easy access to it all.
$92 per night
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Farm stay in Cape Charles
Private Guesthouse on Secluded Waterfront Farm
Just 5 miles from Cape Charles and 30 minutes from Virginia Beach, our contemporary Guesthouse gives you the peace and solitude characteristic of the Eastern Shore along with the convenience of being close to urban centers. Our twenty acre waterfront farm, which has plenty of nearby walking or biking, and a dock onto a secluded arm of Plantation Creek, an inlet of the Chesapeake Bay, is perfect for couples or small families looking for a memorable trip to the Eastern Shore.
$129 per night
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Vacation rentals for every style

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Stay near Cape Charles's top sights

Photo of The Shanty
The Shanty65 locals recommend
Photo of Cape Charles Brewing Company
Cape Charles Brewing Company47 locals recommend
Photo of Deadrise Pies
Deadrise Pies30 locals recommend
Photo of Cape Charles Coffee House
Cape Charles Coffee House25 locals recommend
Photo of Brown Dog Ice Cream
Brown Dog Ice Cream38 locals recommend
Photo of Cape Charles Fishing Pier
Cape Charles Fishing Pier14 locals recommend

Other great vacation rentals in Cape Charles

Guest suite in Cape Charles
Chesapeake Retreat - Bay view
$97 per night
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Home in Cape Charles
Modern Private Beach House close to Cape Charles
$450 per night
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Vacation home in Cape Charles
Beach, Park, Bakery & Downtown within blocks
$149 per night
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Home in Cape Charles
Casa de Coconut, 2 blocks from beach!
$143 per night
Guest suite in Cape Charles
The Minnow (Lovely studio near beach)
$185 per night
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Home in Cape Charles
Charming, Historic Cape Charles House-Pet Friendly
$161 per night
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Tiny home in Cape Charles
Smith Beach. Unique, luxurious creekside stay
$152 per night
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Home in Cape Charles
Bay Breeze on Tazewell -walk to the beach!
$150 per night
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Home in Cape Charles
Peach Haven I: Close to beach and park!
$160 per night
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Loft in Cape Charles
The Cheriton Loft
$65 per night
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Farm stay in Cape Charles
Airstream Retreat Farm Stay Cape Charles
$180 per night
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Tiny home in Machipongo
Machipongo Glamper
$60 per night
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Your guide to Cape Charles

Welcome to Cape Charles

Cape Charles sits at the southernmost tip of the Delmarva Peninsula on Virginia’s Eastern Shore, a long peninsula with Chesapeake Bay to the west, Kings Creek to the north, and Old Plantation Creek to the southeast. This town of 1,000 full-time residents is known primarily as a beach destination, especially since the Cape Charles Town Beach remains the only public beach on Virginia’s Eastern Shore that doesn’t charge fees (not even parking fees!). Beyond its sandy shores, Cape Charles’ main draws include a fishing pier, an outdoor LOVE sign popular with photographers, and a historic district boasting one of the highest concentrations of turn-of-the-century homes. Originally developed as the headquarters of the Eastern Shore Railroad, Cape Charles’ strategic location also makes it a prime area for geographic diversity and bird spotting.


When is the best time to stay in a vacation rental in Cape Charles?

Summer is the busiest time of year at this popular outdoor destination, peaking in June through August. It’s also the hottest time of year, often with humid days. There are plenty of things to do during this time, such as the free summer concerts and food festivals, including the Cape Charles Crabby Blues Festival and the Reel and Raw oyster festival. Spring and the early fall months may also be a good time to stay in one of the area’s rentals since the humidity makes the air feel a bit warmer. December through February are too chilly for outdoor fun, especially with the rain and snow that tends to fall four to six times a year. But the season does bring its own fun, such as Festive Fridays and the Lighted Golf Cart Parade leading up to Christmas, and a Dropping of the Crab Pot to ring in the New Year.


What are the top things to do in Cape Charles?

Historic District

Turn back time in the historic district filled with buildings from the late Victorian, Colonial Revival, and Neoclassical styles built from 1885 to 1940, mostly in a 27-block grid with a central park featuring a pergola, gazebo, and fountain. The high concentration of preserved buildings put the area onto the National Register of Historic Places in 1989.

Cape Charles Natural Area Preserve

Follow the boardwalk path leading to a Chesapeake Bay viewpoint through various forested terrains in the 29-acre preserve, including the rare Maritime Dune Woodland. Birders will especially appreciate the more than 240 species that have been spotted here.

Cape Charles Museum

Run by the Cape Charles Historical Society, the museum includes an indoor section with historical relics of the area, including Chesapeake Bay steamship and ferry models, as well as an outdoor section with actual railroad cars and a recreation of the Bloxom railway station.