Waterfront vacation rentals in Cape Charles

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.

Romantic Sailboat Experience + Seafood Restaurant

We can't adequately describe how romantic & carefree it feels to step aboard our sail boat. The perfect stay begins by treating yourselves to dinner at the marina's seafood restaurant, then snuggle up together on deck to watch the sunset turn the sky pink & purple. The marina atmosphere is simply magical & you'll love rocking with the gentle sway of calm waters. Come enjoy a weekend aboard this amazingly cozy & romantic sail boat. Convenient to Norfolk & Virginia Beach, the location is prime!

Unique style, Waterfront Dock,Yard,Kayaks,SUP,King

Nestled on Little Oyster Creek in the charming small town of White Stone, is Beacon Bay Getaway. This lighthouse style home is situated on 3 private acres and has 3 water views: the Creek, the Chesapeake Bay and the Rappahannock River all which can be viewed from the wrap @ deck and top observation lookout. Enjoy the large yard with fire pit. Launch a kayak/SUP from our dock or bring your fishing rods to catch Croaker. Have fun catching blue crabs with our crab traps. Follow @beaconbaygetaway

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.

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!

Private romantic pet friendly waterfront cottage

On Virginia’s beautiful Eastern Shore, The Birdhouse at Windfall Farm is the ultimate romantic getaway. Just steps from Pungoteague Creek (a short boat ride to the Chesapeake Bay)on one side and a picturesque large stocked pond on the other, The Birdhouse is a charming 1 bedroom hideaway, with abundant wildlife, walking trails on our 62 acre working farm, kayaking, fishing, crabbing, and stargazing, all amid Nature’s beauty. Be our guest for an unforgettable time on Virginia’s Eastern Shore!

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

Egret’s Point on the Creek

Egrets Point on the Creek, is a beautiful and peaceful place to relax and plan your Eastern Shore exploration. Whether you are enjoying the fire pit by the creek, or taking a nap in the hammocks, canoeing, walking or exploring historic Onancock, life by the creek is sweet. Chincoteague to the north, Cape Charles to the south. Excitement abounds. Coastal exploration, boating, fishing, fine dining, artisan shops, art galleries, farmers markets and sandy beaches. Come and enjoy!

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.