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Cape Charles Home: Private Pier & Beach-Front Deck

Experience the serene luxuries of coastal living when you stay at this newly built 4-bed, 3-bath vacation rental in Cape Charles! Boasting a spacious interior, a private waterfront deck, and direct access to a private beach along the Chesapeake Bay, 'The Sea Suite' invites you to explore the best of Virginia with style and ease. Watch as the local wildlife roams the scenic landscape of your backyard, take the provided kayaks out for a spin, and unwind in nature at this unforgettable retreat!

Shore Is Fun: Private Beach, Pool & Bunk Room!

Tucked away on a private drive, this spacious getaway offers breathtaking sunsets, exclusive beach access, and all the comforts of home. Just steps away, enjoy a swim in the community pool or take a short stroll to the private beach. Nearby Cape Charles has something for everyone, including miniature golf, pickleball and tennis courts, boutiques, restaurants, and confectionaries. Whether you’re seeking beach days or small-town charm, this rental is the ideal place to make lasting memories.

Mattawoman Creek Waterfront Estate

Welcome to Mattawoman Creek Estate! Enjoy this peaceful secluded luxurious Waterfront home on 4 acres in Machipongo on the Eastern Shore of VA. This very spacious 5 bedroom, 3.5-bath, home offers a vacation to unwind, refresh, enjoy nature, soak in the Beach sun or Kayak to the Chesapeake Bay from our private dock. For a dose of local charm, explore the town of Cape Charles for the entire family. If fishing excites you, target a Red Drum in the Bay or Hungars for a trophy Speckled Trout!

Eden Guest Suite on Lake Allure

Relax and recharge in nature at this unique and peaceful getaway. Private access to one of Virginia’s best freshwater fishing lakes, with kayaks and SUP included. Just 15 minutes south of Cape Charles and 5 minutes from Kiptopeake, it’s a perfect base for exploring the Shore. Surrounded by nature and just 3 minutes’ drive to Pickett’s Harbor Farm and beach access. The guest suite is separated from the main house, with a private entrance and beautiful garden views for a truly tranquil stay.

The Laughing King Retreat, Parramore Island Suite

The Laughing King Retreat is an adults-only, organic waterfront farm situated directly on the peaceful waters of 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. Dig for clams, collect wild oysters, or just sit and marvel at the beauty.

4BR Waterfront Home with Dock • Pet-Friendly

Welcome to Ripple! Ripple is a large home on 2+ acres on Virginia's Eastern Shore, nestled on Nassawadox Creek and conveniently located between Cape Charles and Onancock. The one-level home features a fully equipped, updated kitchen and open living room with plenty of space to relax inside and out. Enjoy the private dock, screened-in back porch with hanging swing, and a firepit with seating. Well-behaved dogs are welcome with prior disclosure. Large, private property (unfenced).

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.

Family Retreat, In-Ground Pool, plus Private Beach

5 bedrooms and 3 full baths plus an outdoor shower. Sleeps 10 adults. 1/2 mile walk, bike, or drive to our private community beach. Kiptopeke Park, Cape Charles, VA Beach, and Williamsburg. Ideal family get-a-way. Modern and private. Please note: Parties, loud music, or lots of screaming in the yard, are not allowed or tolerated. This is a peaceful and quiet community and we need you to honor that. Otherwise, please book another home for your vacation. Thank 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.

Seaside Fishing Retreat in Peaceful Village

Relax with the whole family at this peaceful seaside retreat. In the quiet water town of Willis Wharf, you'll see water & beautiful sunrises from the front porch! There's a carport to keep your boat safe, & a public boat ramp just minutes away. Rooms are spacious and the house has tons of charm & character. Large eat in kitchen to host family dinners caught fresh from the waters of the Chesapeake Bay. Short drive to downtown Exmore, Silver Beach and other shore towns

The Spinnaker: Private Waterfront Suite Near Bay

Wake up to the sunrise over Lake Foster in this private waterfront suite. This suite overlooks peaceful lake views, creating a boutique hotel-style retreat just minutes from Cape Charles Beach and Main Street. Enjoy your own attached bath and private bedroom, then stroll or take a short ride to the bay before returning to quiet sunset evenings by the water.

Eden Lake House Cape Charles

Eden House is a perfect fairytale hideaway. Surrounded by family farms and a very short drive to the Chesapeake bay beaches and Cape Charles, this is the ultimate Eastern Shore getaway. You are welcome to fish, kayak or SUP from the dock on Lake Allure. Or take a walk on our nature trail and see Bald Eagles, turtles, deer and if you’re lucky - otters!