Holiday rentals with a pool in Cape Charles

New Hot Tub~1st Floor King Bed~Fire Pit~Bunk Room!

Escape to where Bay Views Meet Coastal Comfort Welcome to your home away from home in one of America’s happiest seaside towns. Nestled within a peaceful, gated community, the Majestic Mermaid is more than just a house, it’s the backdrop for your family’s favorite memories. Whether you’re here to watch the legendary Cape Charles sunsets from your third-story deck, cruise the charming streets in a golf cart, or walk just a few steps to the sand, this is the coastal retreat you’ve been looking for.

The Great River Escape *Hot Tub!

Welcome to the River Escape, where the sun is hot and river breezes are cool! Located on the Hampton River, on a big fenced lot, with easy river access and just a 10 minute drive to sandy toes and the sound of crashing waves, this fantastic river house is made for the best family vacations around. It is furnished to comfortably sleep 6, featuring a spacious, well-stocked kitchen, private in-ground pool, hot tuband a gas grill in the backyard! Just add family, and you've got instant vacation fun!

Millionaire $ Views No Xtra Charge! Hot Tub! POOL!

Welcome to The Cottage at Misti Cove, where you can experience the epitome of relaxation and tranquility. Immerse yourself in the serene ambiance of our cottage, aptly named for its simplicity, which belies the luxurious amenities that await you. At The Cottage at Misti Cove, we understand that the essence of a fulfilling vacation lies in the delicate balance between embracing the simple life and indulging in modern comforts. Here, you will discover a haven that seamlessly blends these elements

Hot Tub - Massage Chair - Golf Cart - Beach Gear

Whether you are looking for some rest and relaxation, a home-base for the beach or water activities, or a place that comfortably allows you to bring your pets, you are sure to find your desired experience at Paws at the Beach. Open concept space with large glass doors and window to bring in natural light. Sunset room with multiple entertainment options, a massage chair in the living room and a Hot Tub. Four bedrooms that comfortably sleep 10. Rental includes access to a four-seater golf cart!

Blue Heron WaterSide

Blue Heron Waterside awaits you...Private Hot Tub and Pool!Waterfront and Pier- Kayaks included! This retreat is set up with you in mind for a special get away.Relax.Enjoy being together plus space to have quiet time. Sunroom, spacious deck, private Pool, Hot tub and Pier create a waterfront living experience. Grab a book, go for a swim or lounge by the pool. Explore the water with a variety of Kayaks plus a Stand Up Paddle Board.Great location to fish and crab from the pier. Are you ready?

The Barn at Pond Point - Riverfront Home

The Barn at Pond Point is perfectly situated on the Piankatank River, a salt water arm of the Chesapeake Bay. It shares 19 acres of wooded and waterfront property with the owner's main home. A unique space, Barn was converted from a working horse barn into a residence in the 1980's. With a quarter mile of private, sand beach and a large pool (May-Sept), the Barn is an ideal space for time with family and friends, swimming, hunting for prehistoric shark's teeth, or simply enjoying the view.

“Old Smokey”A cozy, single bedroom, unique getaway

"Old Smokey" is a 1965 pull-behind camper that has been beautifully remodeled. It is cozy, rustic and has been restructured with lots of love. You can enjoy breathtaking sunrises and sunsets. The camper has both air conditioning and a wood stove. "Old Smokey" is a unique and romantic glamping experience. You can cook delicious meals on the propane stove/grill or visit one of our charming local restaurants. This is the perfect location to relax and reset, either solo or with someone special.

"Shangri-La", of Hampton, Virginia

2nd story 1200 square foot apartment with 2 BR's, Wi-Fi, microwave, fridge and bar with sink. Walk in glass enclosed shower & soaker tub. Private deck with gas grill down the spiral stairs below on ground level patio. Pool table in BnB. We share our pool with our BnB guests seasonally. Please inquire about pool availability if important to your booking. Local history, sites, nature and beaches abound. Security cameras surround the exterior of our home for our protection as well as yours!

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.

Heartsong Farmhouse , a nature lover's retreat.

Heartsong Farmhouse was completely renovated in 2019. Beautiful hardwood floors, brand new furniture, in a modern farmhouse style with a Boho vibe. The entire home is filled with beautiful natural light and the brick walls ensure a peaceful nights sleep. The yard is completely surrounded by a 15ft hedgerow of holly, magnolia and camellias, like walking into a secret garden. You will feel welcome from the moment you drive up. The Farmhouse is also beautifully decorated for the holidays.

Oysterman's Pearl Golf Cart Included

Luxury Home with Golf cart included! Spacious beach house with a luxury touches. Great place to escape and enjoy the private amenities of Bay Creek while being a short walk or golf cart ride to downtown Cape Charles. Relax on the screened in porch or enjoy the breeze from the crows nest on the 3rd floor. This home has everything you need to have a relaxing beach vacation with the comforts of feeling at home. Bay Creek HOA pool, tennis courts, and YMCA pool and gym passes included.

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.