Vacation rentals with a kayak in Cape Charles

The Hideaway at Mill Creek

We welcome 6 persons, however 4 adults max. Here you will find nestled in the woods atop a beautiful hill overlooking Mill Creek, a short distance from the Chesapeake Bay, an architect's home. With beautiful sunrises and sunsets, this hideaway gives you an escape from everyday life. Relax on the patio with a book, out on the water kayaking, fishing or crabbing off the dock or sitting watching the wildlife. You will never forget the views or the sight of the sailboats in for a rest from the bay.

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 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

Cottage on Prentice Creek

Freshly painted cozy two Bedroom Cottage with a Sectional Sofa that has queen bed pull out. Screened Porch, Large Patio & Dock to enjoy views of the creek and wildlife. Great for a romantic getaway or vacation. Well-appointed kitchen. Dogs allowed (2 Max, under 70 pounds-must be notified first) an additional fee of $60 per dog. No third-party bookings. Just outside Kilmarnock, very close to White Stone and Irvington with a good variety of Restaurants, Wineries, Breweries a Cidery and shopping.

Harbor View- (Sun - Sun rental June- Aug.)

Harbor View is an early 1900's brick duplex with high ceilings, transom windows, and crown molding. Best of all, this home is located in a quiet neighborhood just one block from the beach and two blocks from Mason Ave. where you can find unique shops, restaurants and other amenities. It's an easy walk to the pier for a magnificent sunset, or to Brown Dog's for homemade ice cream. We invite you to enjoy our comfortable home, and explore the quiet ambience of a historic beach town vacation!

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!

Cottage by the bay (private peaceful surroundings)

Privacy, peace, relaxation, togetherness … this cottage is the perfect place for memory-making with your family and friends!     The kitchen is stocked with every spice and tool you may require to create a delicious meal, which can be enjoyed at the breakfast bar, large dining table, or outside, surrounded by the tranquil Virginia ambience.     The shed, equipped with kayaks, paddle board, crabbing gear, bicycles, beach stuff chairs, has all you may need for a day on the bay or at the ocean.

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

1891 Coastal Charmer: fully renovated farmhouse

Built in 1891, this farmhouse has been totally renovated by a professional designer. The Cottage is filled with coastal colors and accessories so it feels fun and updated but still retains the feeling of walking into a well loved family beach cottage. We are pet friendly as any beach cottage should be and love seeing our guests and their pets enjoying the cottage. Follow the cottage on social media @ BlueOysterCottage for more pictures, design ideas and local places to visit.