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Cape Charles cottage, family friendly, in town

Welcome to Cape Charles Cottage in the historic district! We are 6 blocks to the beach and 4 blocks to Mason ave (shops, restaurants). The town is very walkable or golf cartable…you can rent ours! We can host up to 10 guests with 4 bedrooms and a bonus room with a daybed w trundle that pulls to side by side twins. One bedroom has an ensuite bathroom and the others share a hall bath with a tub/shower. Kitchen is fully equipped, fenced yard, outdoor shower,fire pit, grill & shed with beach gear.

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 town. Our twenty acre waterfront farm, home to both a Vineyard and an Oyster Farm, has plenty of nearby walking or biking and a dock on a secluded arm of the Chesapeake Bay. Our farm is perfect for solo travelers, couples or small families looking for a memorable trip to the Eastern Shore.

Bay Breeze Home on private waterfront

On Virginia's beautiful Eastern Shore, the Bay Breeze Home on Occohannock Creek is the ultimate getaway for two or a large family desiring outside adventures. This 1970's spacious home has plenty of room. Experience the water with our three kayaks or family canoe and watch the abundant wildlife. Right outside your door, you may see Ospreys, Great Blue Herons, Eagles, wild ducks, porpoises, deer, geese, otters, & more. Be our guest and forget your worries in this spacious and serene spot.

The Laughing King Retreat Honeymoon Island Cottage

Honeymoon Island Cottage is an adults-only lodging experience like no other. You and your guest will stay in a charming tiny farmhouse that is located just steps from the Chesapeake Bay on a USDA certified organic farm. Enjoy access to a private saltwater pool, private beach, Chesapeake Bay water access for boating, swimming, paddleboarding, fishing or just soaking, dig for clams, collect wild oysters, or just sit and marvel at the beauty. We look forward to welcoming you.

Ultimate Cabin Farm Stay Cape Charles

Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

Game Barn! Next to Central Park! 2 Blocks 2 Beach/

Welcome to Cape Glen Haven in the Historic District of Cape Charles, where the porch sitting is top notch! The 1933 Craftsman style home has fenced yard & is Pet Friendly! Snuggle up next to the fire pit under the twinkle lights and your very own Game Barn which features, (pool, skee-ball, ping pong, and corn hole). Central location is close to everything! Just 2 blocks walk to the Beach, next to Central Park, and 2 blocks to Restaurants, & boutique shops!

HGTV House! 2 Blocks to Beach- 2024 New Bathroom!

Welcome to Liberty on the Bay (featured on HGTVs Beachfront Bargain Hunt) Our 4 bedroom/2 bathroom (sleeps 10) stunner includes original hardwood floors, a fully updated kitchen, and two outdoor showers. The beautiful front porch is perfect for people-watching or simply escape to the private backyard to relax under the magnolia tree. This spacious house is a quick 5-minute stroll to either the historic town or the beach.

Seabreeze Cottage ... explore the Eastern Shore!

Seabreeze Cottage is located on a country lane just outside the seaside village of Cheriton, less than 5 miles from downtown Cape Charles. This is the perfect home base for you and your family to explore all that Cape Charles and the Eastern Shore has to offer. This home is also a great place for fishing and duck hunting trips, as it is close to several boat launches. We welcome dogs under 55 lbs with $60 pet fee.

Captain's Cottage

The Captain's Cottage was originally built in 1886 and has recently undergone extensive renovations to create a home of charm, history, and comfort. Located a block away from Cape Charles's Central Park, four blocks from the beach, and two blocks from Mason Avenue, the Captain's Cottage is in a prime location in Cape Charles.