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Guesthouse at Vessel Farm & Winery, Waterfront

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.

Unique, luxurious creekside stay in Cape Charles

Recently updated and ready for your next getaway! This tiny home is located just a short minute walk from a calm, private beach. The interior decor creates a modern coastal feel to fit the style of the home. Creek views can be enjoyed from every window of the home and from the loft bed. It features a full kitchen with quartz counter tops, a fully tiled bath, outdoor shower, large front porch and a quaint back yard with added privacy fencing. Enjoy our fire pit with twinkle lights strung above.

The Cheriton Loft

Located in the heart of Cheriton, The Loft is a bright and sunny apartment. It is perfect for a couple and one child, three friends or one person. Cheriton is an up and coming village which is home to several galleries and an art center. It is less than 4 miles to the charming town and beach of Cape Charles, 3 miles to Oyster Boat Landing and 8 miles to Kiptopeke State Park. The apartment is owned and decorated by"The Sheep Lady", a local painter, illustrator and writer of children's books.

Bakery Next Door | Renovated | Golf Cart Avail.

Nectarine 13 is a centrally located. Next door, you’ll find the Coastal Bakery. A great place for breakfast or Treat. Relax on the charming front porch and soak in the calm, historic vibe of Cape Charles. A Quick walk to historic Downtown, Take a swim in the bay or cast a line off the dock. Central Park is also nearby, offering a great spot for a family picnic while the kids enjoy the playground. Golf carts are available to rent(Cart Rentals are only available during the House rental period)

The Waverly Treehouse

Reconnect with nature and sway with the trees in this rustic treehouse nestled away in the woods with a gorgeous view of Hungar's creek. Enjoy the view from the front porch or while relaxing around the fire pit. Visit the adorable beach town of Cape Charles, complete with a beautiful beach, brewery, distillery and plenty of restaurant options, or stop by the nearby vineyard for some local wine. Usage of dock, kayaks, grill, and fire pit all included. Beach towels and cooler also provided.

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.

Private Country Beach Retreat

Welcome to Mason Jar Retreats Beach Home. Our home is a private beachfront property with the best of both country and beach living. Located on 6 acres on a private road with only a few steps to take to your private oasis on the Chesapeake Bay. Enjoy sunsets from the beautiful porches while taking in the natural surroundings. Our home is only three miles from a vineyard and winery and 20 minutes to Cape Charles with lots of shopping and dining in a quaint beach town. *LGBTQ+Friendly Home

The Rudder. Great Views!

Cozy warm cabin! Large kitchen with eating area, bath with tub/shower, bedroom with queen bed, family room with a queen pull out sofa and a separate bedroom with 2 twin beds. Large screened in porch with wonderful views of the Bay. This property is located in Cross Rip campground. Guests of the cabin have access to the beach and pier. This cabin also has an adjoining cabin (like at a hotel) that will sleep an additional 4. Please see our listing for The Stateroom. NO PETS.

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.

Peaceful Waterfront Escape on Church Creek

Welcome to "Big's Place". This house was once home of a great fisherman. Big Jim spent most of his retirement reeling in fish of all kinds from the Chesapeake Bay. He was a beloved figure on the Eastern Shore. The home is now owned by his three sons, who live in the Pittsburgh, PA area. They hope that others will appreciate the shore and all it has to offer just like their father, Big Jim, did.

3 Blocks to Beach, Fenced Yard, Cozy 2BR&2BA

Welcome to Peach Haven II! Renovated in 2021, this pet-friendly duplex in Cape Charles’ historic district sleeps 5. One block from a park with playground and tennis/pickleball courts, and 3 blocks from the beach. Features 1 bedroom (queen bed) and a 2nd with a custom full-size bunkbed. Stocked for comfort. Ask about renting the other side for more space!