Family-friendly rentals near Cape Charles Beachfront

4.98 out of 5 average rating, 102 reviews

A serene beach view is presented, with calm waters stretching toward the horizon. A wooden pier extends into the bay, surrounded by gentle sandy shores and smooth stones. Grassy areas blend seamlessly into the seaside landscape, creating a tranquil outdoor setting.

Home in Gwynn

‘The Sand Crab’- Beachfront Cottage, Kayaks, WiFi

This beachfront cottage is the perfect get away from a busy & hectic life to slow down & enjoy each others company! Situated just over 70 miles from Richmond, this home shares waterfront views of the Chesapeake Bay. Fishing, swimming, kayaking & sun await you at the Sand Crab! What makes it so great? Just steps outside and you're on the beach Newly renovated Cable, high speed Wifi, Netflix 2 screen porches Kayaks and paddle boards Just over 10 minutes to grocery store, ABC, and other shops

The exterior of the home is shown, featuring a welcoming porch with ornate detailing and a pair of rocking chairs. Lush greenery, including bushes and flowers, enhances the inviting atmosphere. The blue siding and white trim reflect the home's historic charm.

4.98 out of 5 average rating, 124 reviews

Bayside Bonanza | Off-street Parking | EV Charger

"Bayside Bonanza" is special. Ideally located with the main street of Cape Charles around the corner in either direction, and a 5 minute walk to the bay or Central Park. There's nothing like sitting on the front porch swing, sipping morning coffee or an evening cocktail. The home is bright and cozy, with efforts made to keep as much of the original 1890's charm as possible. We're family owned and managed, and it's our priority to help you have the most relaxing and enjoyable vacation possible!

Farm stay in Cape Charles

The spacious kitchen features a large island with seating for six, modern appliances, and ample counter space. A bright window above the sink offers views of the surrounding landscape, while soft lighting complements the contemporary design. Light wood flooring enhances the welcoming atmosphere.

5.0 out of 5 average rating, 430 reviews

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.

4.97 out of 5 average rating, 118 reviews

The exterior of the beach cottage features a welcoming porch with seating arrangements. Lush greenery surrounds the home, and blooming flowers add color to the landscape. The symmetrical architecture is complemented by a blue exterior and white trim, contributing to a charming appearance.

Cottage in Cape Charles

The Little Jewel

Newly renovated beach cottage - The Little Jewel. Cozy beach decor with all amenities just bring your swim suit. Full stocked kitchen, if you like to cook. Or one block over is Mason Avenue with restaurants and shopping to enjoy. Enjoy the sunsets on the over sized porch. Perfect for small families and couples. Outdoor shower super nice after long day on beach. We have bikes, and all the beach necessities in the shed. Check out our sister cottage The Little Gem if your dates are not available.

Townhouse in Cape Charles

The living area features a cozy gray sofa, two armchairs, and a circular coffee table. Natural light fills the space through windows adorned with light curtains. A large wall-mounted TV is positioned above a white media console, enhancing the room's modern yet inviting aesthetic.

4.96 out of 5 average rating, 198 reviews

Walk to Beach and Park! Outdoor shower&Fenced Yard

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 four 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. Ask about our optional golf cart rental during your stay!

A classic brick duplex features a large front porch supported by white columns. A ceiling fan hangs in the shaded area, while steps lead up to the entrance. Lush greenery lines the porch, and a clear blue sky complements the welcoming design.

4.92 out of 5 average rating, 171 reviews

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!

5.0 out of 5 average rating, 9 reviews

Home in Bavon

Chesapeake Shore Cottage: Private Beach w/Kayaks

Bayside Getaway on the Chesapeake in Port Haywood: Steps to the Sand! Welcome to your perfect coastal escape! Nestled right on the tranquil shores of the Chesapeake Bay in beautiful Port Haywood, Virginia, this charming beachfront cottage offers the ultimate blend of secluded relaxation and small-town convenience. Whether you’re sipping your morning coffee on the porch as the sunrises over the water or launching a kayak for an afternoon adventure, this is the place where memories are made.

The red brick duplex features a welcoming front porch with white rocking chairs on both sides. Two main entrances are visible, framed by classic black shutters, while the well-maintained yard is accented with small plants. The evening sky casts a gentle light over the structure.

4.94 out of 5 average rating, 193 reviews

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)

4.99 out of 5 average rating, 131 reviews

A two-story beach house stands amidst lush greenery, featuring a spacious wrap-around porch with multiple seating areas. Large windows allow for ample natural light, while the light-colored exterior complements the serene surroundings. The property is partially surrounded by trees, enhancing privacy.

Home in Machipongo

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

4.96 out of 5 average rating, 256 reviews

A two-story cabin made of wood stands beside a serene pond, surrounded by tall pine trees. The cabin features large windows and a spacious deck with rocking chairs, inviting peaceful moments by the water's edge.

Cabin in Cape Charles

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, feed the Alpacas, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

The front porch features two bright yellow doors welcoming guests, flanked by white railings and steps leading up to the entry. Potted plants and green grass enhance the outdoor space, while a large tree provides shade in this inviting setting.

5.0 out of 5 average rating, 104 reviews

The BeeHouse

Breathe in the Beehouse! Newly built, this well equipped modern house features high ceilings with a clean crisp design with bright tropical colors and natural touches that truly transport you! Treat yourself to the tranquil Cape Charles lifestyle where you won’t see a clock because the local church chimes on the hour. Huge outdoor living space embraces you and allows you to take it all in. Have the sweetest vacation at the Beehouse!

A charming duplex exterior features a light yellow facade with blue shutters and a welcoming covered porch. White steps lead to two front doors, flanked by lush greenery, including flowering hydrangeas. The evening sky adds a soft hue in the background.

4.94 out of 5 average rating, 121 reviews

The Shore House on Madison - Pet Friendly Unit!

The Shore House on Madison was fully renovated in 2019 and located in the Cape Charles Historic District within walking distance to the beach, park, the shops and restaurants. Our pet friendly unit can host up to 7 guests with 3 bedrooms, 2 full baths and 1 outdoor shower. Bedroom #1 includes 1 Queen bed, TV and work desk. Bedroom #2: 1 Queen bed. Bedroom #3: Bunk Bed (1 double / 1 twin). Fenced in backyard with patio.

Popular amenities for family-friendly rentals near Cape Charles Beachfront

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.98 out of 5 average rating, 175 reviews

A spacious deck extends towards the waterfront, surrounded by lush trees. Lounge chairs and seating areas are positioned for relaxing views of the calm water. A sunroom is visible to the right, offering additional indoor space. The overall setting invites outdoor leisure and tranquility.

Home in Cobbs Creek

Blue Heron WaterSide

4.96 out of 5 average rating, 161 reviews

An aerial view captures the spacious backyard featuring a rectangular swimming pool surrounded by a concrete deck. Lounge chairs are placed by the poolside, with a well-maintained lawn and shrubs in the background. The two-story cottage is shown with a screened porch and a shaded area nearby.

Cottage in Chesapeake

The Cottage @ Captain Genes - Secluded Waterfront

4.91 out of 5 average rating, 181 reviews

Home in Cobbs Creek

Million $ Views! Pool! Private Hot Tub! EV Charger

4.9 out of 5 average rating, 265 reviews

A hot tub is positioned on a wooden deck, overlooking the shimmering waters of the Chesapeake Bay. Surrounding greenery includes tall grasses and trees, with the expansive view of the water framed by a clear blue sky.

Cottage in Reedville

Bay cottage 🏖on the beach. Stunning views🏝

Guesthouse in Gloucester County

A winding gravel pathway is illuminated by soft lighting, bordered by lush greenery. String lights are hung above, casting a warm glow over the area, which is surrounded by trees and plantings. A staircase leads to an elevated area in the background.

4.98 out of 5 average rating, 241 reviews

Stylish Creekside Cabin w/ HotTub, Parklike views.

4.93 out of 5 average rating, 156 reviews

An aerial view of a serene waterfront property is depicted, showcasing a spacious home surrounded by trees. A private dock extends into the calm waters, reflecting the trees along the shoreline, highlighting the tranquil setting.

Home in Heathsville

The Hideaway at Mill Creek

4.95 out of 5 average rating, 180 reviews

Home in Irvington

Magical wooded cottage pool +priv hottub walk2town

4.93 out of 5 average rating, 105 reviews

A modern living area features a comfortable sofa adorned with decorative pillows and a cozy throw. A large dining table with natural wood tones is visible in the background, contrasting against a blue accent wall decorated with serene artwork. Ample lighting brightens the space.

Home in Norfolk

Stylish Beach House, Hot Tub, Pet Friendly

Family- and pet-friendly home rentals

Tiny home in Cape Charles

A charming two-story cottage is set on a lush green lawn, with a clear view of the Chesapeake Bay in the background. The cottage features large windows and a sloped roof, with a small wooden addition on one side, surrounded by well-maintained grass.

4.98 out of 5 average rating, 360 reviews

The Laughing King Retreat Honeymoon Island Cottage

4.95 out of 5 average rating, 233 reviews

The interior of the tiny cabin showcases a unique staircase leading to a lofted sleeping area. Natural wood elements are highlighted throughout, with a clear roof allowing natural light to fill the space. A doorway opens to the outdoors, enhancing the cabin's connection to nature.

Tiny home in Diggs

Stargazer Tiny Cabin

4.95 out of 5 average rating, 143 reviews

A serene beach area is depicted at sunset, with soft waves lapping against a sandy shore. The water reflects golden hues, and trees line the distant shoreline, creating a peaceful natural setting.

Barn in Cobbs Creek

The Barn at Pond Point - Riverfront Home

Place to stay in White Stone

4.99 out of 5 average rating, 125 reviews

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

A two-story blue house is framed by white trim and windows, showcasing a welcoming front porch and a white picket fence. A golf cart is conveniently parked in front, with a patio umbrella visible on the side, indicating outdoor leisure space.

4.95 out of 5 average rating, 108 reviews

Historic, Pet Friendly Cottage-Three Little Birds

4.78 out of 5 average rating, 163 reviews

A sandy beach stretches along the water's edge, with a house featuring large windows nestled among green shrubs. A lighted pier extends into the water, where two children are playing. The clear sky and surrounding trees create a serene backdrop.

Cottage in Deltaville

Stunning Beachfront Cottage on the Chesapeake

4.97 out of 5 average rating, 156 reviews

Four black Adirondack chairs are positioned in a grassy area facing a tranquil body of water. Lush green reeds frame the water's edge, with a blue sky and scattered clouds above. A small dock is visible in the distance, adding to the serene setting.

Home in Belle Haven

Bay Breeze Home on private waterfront

4.91 out of 5 average rating, 125 reviews

A serene sunset is captured over calm waters, with hues of orange and gold reflecting on the surface. Silhouettes of trees frame the scene, while a dock extends into the bay, creating a tranquil coastal atmosphere.

Cottage in Painter

Cottage by the bay (private peaceful surroundings)

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 222 reviews

A spacious waterfront home is showcased with a well-maintained lawn and blooming yellow flowers near the entrance. A large driveway leads to a brick facade, complemented by a garage. Clear blue skies can be seen in the background, enhancing the welcoming appearance of the property.

Home in Gloucester Point

York River Vacation Home

4.96 out of 5 average rating, 169 reviews

A tranquil waterfront scene features a wooden pier extending into the calm waters of the East River. Lush greenery frames the image, while gentle waves reflect the soft sky above. Nearby trees provide shade, creating a serene atmosphere for relaxation and contemplation.

Cottage in Cardinal

Haddie James House - A Coastal Va AirBnB

4.98 out of 5 average rating, 307 reviews

A green pasture is featured, where a group of five horses graze peacefully. The background showcases a wooded area with tall trees, under a clear blue sky. A small shelter is visible in the distance, complementing the tranquil rural setting.

Home in Accomac

Heartsong Farmhouse , a nature lover's retreat.

5.0 out of 5 average rating, 200 reviews

Guesthouse in Gloucester

Cozy Fall Retreat - Creek Views & Fire Pits

4.96 out of 5 average rating, 298 reviews

Cottage in Norfolk

Positano Villa

5.0 out of 5 average rating, 131 reviews

A clear blue pool is framed by wooden decking and lush greenery. The inviting water reflects the sky, and the pool features a set of steps for easy access. Surrounding the pool are wooden railings, adding to the private feel of the outdoor space.

Apartment in Irvington

Pelican Place, Cozy Retreat | Pool | Walk to Tides

4.91 out of 5 average rating, 138 reviews

Home in Hampton

4BD home w/ game room & pool near Langley & PTC!

4.93 out of 5 average rating, 121 reviews

A serene river view is captured at sunset, showcasing vibrant hues of orange, pink, and purple across the sky. A wooden pier extends into the water, backed by silhouetted trees. The calm surface reflects the colorful sky, creating a tranquil atmosphere.

Guesthouse in Gloucester

Clay Bank River Front Cottage

Family-friendly home rentals with Wi-Fi

5.0 out of 5 average rating, 19 reviews

Chateau-de-Chuck

A charming two-story house is presented, featuring light blue siding and a welcoming front porch. Lush greenery surrounds the property, and a stone pathway leads to the entrance. A screened porch can be observed that enhances the outdoor living space.

5.0 out of 5 average rating, 28 reviews

Historic Cape Charles- 1 Block from the Beach!

A three-story home is showcased with a light blue exterior and white trim. Balconies are present on the upper floors, surrounded by white railings. Lush greenery and colorful flowers adorn the front yard, complemented by a neatly maintained lawn.

5.0 out of 5 average rating, 24 reviews

Legasea by the Bay

5.0 out of 5 average rating, 4 reviews

Golf Cart Included~1 Block to Beach! Grill~Patios!

A charming light grey cottage is surrounded by a white picket fence, featuring a neatly landscaped yard with grassy patches and flowering plants. A spacious front porch with white steps leads to the entrance, creating an inviting atmosphere. Neighboring houses can be seen in the background.

4.93 out of 5 average rating, 46 reviews

Sheller Shack - 2 blocks from the bay!

The historic two-story brick home features a welcoming front porch with white railings and blue doors. An American flag is displayed, while shrubs and greenery frame the entrance. The structure showcases traditional architectural elements, blending modern updates with classic charm.

5.0 out of 5 average rating, 16 reviews

Sol Mate: Sunrise Cape Charles Shore Retreat

The exterior of a light blue two-story house is shown, featuring a welcoming front porch with a white railing. A mint green front door is centered, flanked by large windows. Lush greenery lines the walkway, enhancing the inviting appearance of the home.

5.0 out of 5 average rating, 77 reviews

Breakwater Cottage

An inviting front porch features a pastel blue-green siding with a vibrant coral door. Two white adirondack chairs sit beside a small potted plant, while a pink swing offers a warm touch, enhancing the welcoming entrance to the home.