Vacation rentals in Cape Charles

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 out of 5 average rating, 397 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.

4.98 out of 5 average rating, 102 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.

4.93 out of 5 average rating, 257 reviews

A cozy sleeping area features a spacious bed with a light-colored quilt, complemented by decorative pillows. A comfortable seating area includes a sofa and a side table, while a patterned rug adds warmth. Natural light filters through a window adorned with light curtains.

Loft in Cape Charles

The Cheriton Loft

Located in the heart of Cheriton, The Loft is a bright and sunny apartment. It is perfect for a couple and one child, three friends or one person. Cheriton is an up and coming village which is home to several galleries and an art center. It is less than 4 miles to the charming town and beach of Cape Charles, 3 miles to Oyster Boat Landing and 8 miles to Kiptopeke State Park. The apartment is owned and decorated by"The Sheep Lady", a local painter, illustrator and writer of children's books.

4.99 out of 5 average rating, 281 reviews

A wooden deck is shown overlooking a serene pond, framed by lush trees. A dining table with chairs is set for outdoor enjoyment, while soft natural light reflects off the water's surface, creating a peaceful ambiance.

Farm stay in Onancock

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 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.

4.93 out of 5 average rating, 138 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)

The exterior of the cottage features a charming design with a sloped roof and textured blue siding. A welcoming porch is supported by white railings, inviting visitors to relax. Surrounding greenery adds to the serene atmosphere, complemented by clear skies overhead.

4.98 out of 5 average rating, 253 reviews

Bay Breeze on Tazewell (Sun-Sun rental June-Aug.)

Bay Breeze on Tazewell is a recently remodeled Cassatt cottage with historic charm and modern amenities. The home includes a fabulous, sunny kitchen stocked to meet your needs. We provide fresh linens and towels for your stay. In the shed, you will find lots of items for the beach, a wagon, and bikes which we are happy to share. Bay Breeze is just a short walk to the beach, various restaurants, boutiques, and marina. If our home is not available, try our new Airbnb home ...Harbor View!

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, 157 reviews

3 Blocks to Beach, Fenced Backyard, Pet Friendly!

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 five 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. Need more space? Ask about renting the other side, too!

A peaceful porch features four white rocking chairs with coral-striped cushions, positioned against a light blue wall. The smooth wooden floor enhances the inviting atmosphere, making it a perfect spot for relaxation.

4.96 out of 5 average rating, 110 reviews

Cape Charles Retreat - 2 Blocks from Beach/Town

Welcome to Cape Charles Retreat! Come on up to the porch, grab a lemonade and settle into the porch swing for some much deserved rest and relaxation. Cape Charles Retreat is a beautiful 100+ year old American Foursquare located two blocks from the beach, Central Park, and town! Our home has been restored to preserve much of its original charm while adding modern amenities and outfitted with everything you’ll need for a great beach vacation. So grab your bathing suit and come for a visit!

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, 332 reviews

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.

A charming beach cottage displays a light yellow exterior with classic shutters and a welcoming porch. An American flag is mounted on the porch, and neatly landscaped greenery frames the entrance, creating an inviting approach to the home.

4.99 out of 5 average rating, 113 reviews

Sun & fun at Sundrop

This gracious beach cottage is the perfect place for you and your family/friends to unwind and enjoy. The sun drenched living room and dining room with wood floors throughout are made for lounging, book reading and family gatherings. We have games and movies aplenty for the kids as well as a collection of outdoor toys to play in the fenced backyard. The kitchen is fully stocked and the high-speed wifi and Roku TV are ready if you need to check email or unwind with a movie.

4.96 out of 5 average rating, 197 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, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

The exterior of a two-story home features a light yellow facade with white shutters. A welcoming front porch is adorned with a seasonal wreath and multiple steps leading up to the entrance, while well-maintained landscaping surrounds the base.

4.96 out of 5 average rating, 112 reviews

Sunshine Rays | Parking | Outdoor Fire Pit/Shower

Situated on a peaceful block of Cape Charles' charming historic district, Sunshine Rays was designed as a retreat for families visiting the Eastern Shore. With space for up to eight guests, an incredible backyard, and thoughtful amenities throughout, it's the perfect base for your Cape Charles getaway. We are just six blocks from the beach and even closer to our Central Park and the town's main street with all of its restaurants, bakeries, and shops.

Vacation rentals for every style

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Cottages

Quaint homes, peaceful surroundings

Popular amenities for Cape Charles vacation rentals

Cape Charles beach vacation rentals

4.97 out of 5 average rating, 261 reviews

An aerial view showcases a private beach beside a rectangular saltwater pool, surrounded by open grassy areas, perfect for outdoor activities. The landscape features a clear path leading from the property to the beach, with residential buildings on one side.

Cottage in Norfolk

Positano Villa

Cottage in East Ocean View

A tranquil beach scene is captured, featuring smooth sandy stretches bordered by green grass and gentle dunes. The horizon reveals a calm ocean meeting a partly cloudy sky, creating a serene atmosphere that invites relaxation and reflection.

4.99 out of 5 average rating, 268 reviews

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

4.99 out of 5 average rating, 141 reviews

Cottage in Norfolk

Private Beach Access at The OV Beach House

Superhost

A spacious yard features a hammock suspended between two trees, overlooking the bay. Colorful Adirondack chairs are positioned nearby, creating an inviting spot for relaxation. The calm water stretches into the distance under a clear sky, providing a serene atmosphere.

Cottage in Reedville

4.88 out of 5 average rating, 222 reviews

Private point on the Bay🌤hammock, hot tub, kayaks❤️

4.94 out of 5 average rating, 177 reviews

An airy living area features a light blue ceiling and large windows offering views of the water. A sleek ceiling fan rotates above a neutral-toned sofa and armchair. A small dining table is positioned near the kitchen, enhancing the open layout that invites relaxation.

Cottage in Port Haywood

Modern Beachfront Cottage with Endless Bay Views

Guest suite in East Ocean View

A beachfront suite is nestled among soft sand dunes, bordered by wood fencing and patches of beach grass. The property features a multi-level structure with an expansive deck. The sandy beach area is directly accessible, enhancing the connection to the Chesapeake Bay.

4.93 out of 5 average rating, 601 reviews

Beachfront Exclusive Bay front Suite

4.97 out of 5 average rating, 307 reviews

A red cabin is surrounded by tall trees, with sunlight filtering through the leaves. The cabin features a screened-in porch at the front and several windows, inviting natural light into the interior. A patio area is visible in the foreground.

Cabin in Deltaville

"The Little Red Cabin" aka The Galley

Superhost

Cottage in Willoughby

4.91 out of 5 average rating, 189 reviews

Poseidon - Beach Carriage House - 120 Years Old

Cape Charles house rentals

A spacious outdoor dining area is set with a long wooden table and benches. The table is adorned with plates, glasses, and a bottle of wine, surrounded by charming blue-hued houses. String lights are suspended above, casting a warm glow over the inviting setting.

5 out of 5 average rating, 50 reviews

Anchors Aweigh

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 out of 5 average rating, 55 reviews

Breakwater Cottage

A charming two-story beach house is presented with yellow siding and blue shutters. A white picket fence surrounds the front yard, while fish-shaped decorations adorn the exterior. A welcoming porch features a green front door, inviting guests to relax in the coastal atmosphere.

4.94 out of 5 average rating, 216 reviews

Inviting house nearby beach and shops!

4.99 out of 5 average rating, 120 reviews

Home in White Stone

1891 Coastal Charmer: fully renovated farmhouse

4.98 out of 5 average rating, 162 reviews

A paved driveway is framed by trees on either side, leading to a two-story home with a welcoming front porch. A white picket fence borders the property, complemented by vibrant yellow flowers in the garden, creating a serene entrance.

Home in Cobbs Creek

Blue Heron WaterSide

4.97 out of 5 average rating, 126 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

Superhost

The exterior of the home features a welcoming yellow door framed by blue and white stripes. Surrounded by green foliage, the porch includes a wooden ramp for accessibility. Large windows provide a glimpse of the interiors, softly illuminated by warm lighting.

4.85 out of 5 average rating, 111 reviews

"Live Life Sunnyside Up" - Minutes From The Beach!

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.

4.95 out of 5 average rating, 99 reviews

The Shore House on Madison - Pet Friendly Unit!

Beach house rentals in Cape Charles

4.92 out of 5 average rating, 372 reviews

The image captures a serene beach scene at sunset, with soft pink and orange hues reflecting off calm waters. The sandy shoreline features gentle dunes and sparse vegetation, creating an inviting atmosphere for relaxation and contemplation.

Home in East Ocean View

New Beach Home on the Chesapeake Bay

An aerial view captures the single-story ranch home positioned across from the beach. Sandy shores extend alongside the calm water, while charming residential streets and greenery surround the property, highlighting its prime coastal location.

4.94 out of 5 average rating, 31 reviews

FREE Luxury Golf Cart - across from CC Beach

5 out of 5 average rating, 123 reviews

A modern kitchen features white cabinetry and a granite countertop, equipped with stainless steel appliances including a stove and a refrigerator. Under-cabinet lighting enhances the space, and ample storage is provided by multiple upper and lower cabinets. A sink is positioned near a window, allowing natural light.

Home in East Ocean View

Quiet East Beach Bungalow, 1 block to beach!

4.94 out of 5 average rating, 118 reviews

A fully renovated historic farmhouse displays a white exterior with a metal roof, set amid lush greenery. The inviting porch features seating options, and a second-floor balcony offers additional relaxation space. The expansive yard invites outdoor activities and creates a serene atmosphere.

Home in White Stone

Coastal Farmhouse Getaway

5 out of 5 average rating, 76 reviews

Home in Reedville

The Haven On The Chesapeake Bay

5 out of 5 average rating, 133 reviews

The kitchen showcases leathered granite counters and a large island with seating. Large windows provide natural light and stunning river views. Cozy seating areas are arranged with colorful cushions, and a gas fireplace adds comfort to the inviting open space.

Home in Deltaville

"No Bad Days" in this Fabulous Beachhouse w/ Dock!

4.95 out of 5 average rating, 55 reviews

The image features a new white single-story home with a front porch, surrounded by greenery. Below, a sandy beach area is visible with a blue and white striped umbrella, leading to calm waters. A wooden pier extends into the bay.

Home in Reedville

Summer Breeze waterfront new home-Private Beach