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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.

Pretty Byrd Cottage, a Victorian Bayfront Getaway!

Imagine getting away from it all by crossing a footbridge to a private island with a Victorian cottage on your own private 3-acre lake! This property is a unique oasis that combines today's modern conveniences with the charm of elegant decor. Enter the front door and be taken in by the surrounding water views, and enjoy charming verandas and a balcony that overlook the lake and gardens surrounding the cottage. Guests can also enjoy the use of a private beach, fishing, kayaks and a paddleboat!

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.

A Charming Low Key Luxe Retreat

Your perfect escape where sophisticated elegance meets coastal charm located in the heart of historic Cape Charles. This stylish, cape-chic getaway offers a serene retreat with everything you need, just steps from pristine beaches, local eateries, quaint shops, and the infamous central park. The beautifully appointed interiors offer every comfort, featuring cozy bedrooms, inviting living spaces, and a well-equipped kitchen, perfect for unwinding or entertaining after a day of beachside fun.

Stylishly Renovated | Golf Cart Avail. | Bakery!

Nectarine 15 is 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)

Historic Charm & Modern Comfort : Downtown Escape

Surrounded by an array of restaurants, bakeries and a variety of unique boutiques and experiences, this apartment offers the perfect blend of charm and convenience. Juliette balconies invite fresh air and natural light, creating a Parisian-inspired ambiance. Inside, a fireplace creates a cozy setting. The state-of-the-art kitchen, designed in a striking 1950s vintage style, features Smeg appliances and bold crimson red accents, seamlessly blending retro elegance with modern functionality.

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

Bay Breeze on Tazewell (Sun-Sun rental June-Aug.)

Bay Breeze on Tazewell is a recently remodeled Cassatt cottage with historic charm and modern amenities. The home includes a fabulous, sunny kitchen stocked to meet your needs. We provide fresh linens and towels for your stay. In the shed, you will find lots of items for the beach, a wagon, and bikes which we are happy to share. Bay Breeze is just a short walk to the beach, various restaurants, boutiques, and marina. If our home is not available, try our new Airbnb home ...Harbor View!

3 Blocks to Beach, Fenced Backyard, Pet Friendly!

Welcome to Peach Haven, a newly renovated duplex in the Cape Charles historic district. Just 1 block from the park and 3 blocks from the beach, it's the ideal base for your Cape Charles escape. This pet-friendly rental sleeps five guests comfortably with a master bedroom (queen bed) and a second bedroom with a custom-made full-over-full bunkbed. The house has been thoughtfully stocked with everything you'll need for a comfortable stay. Need more space? Ask about renting the other side, too!

Summer Camp Tiny Cottage Walk to the beach & shops

At less than 470 sq feet, this 1920s house is super fun & ready to be enjoyed for a couples, friends, and small families! • King sized bed with smart tv on the first floor • Two twin beds in a cozy sleeping loft • Small kitchen with propane stove, Nespresso maker & living space with a smart tv • Patio w/ charcoal grill, solo stove, & dining table • Paddle board & floats Please read through our totally honest disclaimer below! *We have a security camera on the front exterior of the home.

East of the Sun Victorian - Private Pool

Back after a 2-year hiatus! East of the Sun is a fully-restored ca. 1890 Victorian (3 en-suites) with a large screen porch and private, 12' round plunge pool. Our place is ideally suited for 3 couples or families with older children. We welcome younger children as long as parents confirm they're okay with 3 floors/2 sets of stairs, antiques, and a pool. We have a strict limit of 6 guests (however, children under 2-years do not count). We offer a 3-night minimum both low and high season.

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.