Vacation rentals in Cape Charles

4.9 out of 5 average rating, 148 reviews

A cozy bedroom features a spacious bed adorned with soft linens and decorative pillows. Natural light enters through sliding glass doors that open to a deck overlooking the water. A bedside table holds a lamp, with a tray presenting two cups beside a light snack.

Home in Cobbs Creek

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

4.95 out of 5 average rating, 235 reviews

Two white adirondack chairs are positioned on a wooden dock, facing a calm waterway. Soft pastel colors in the sky reflect on the water, creating a serene atmosphere. The surrounding landscape features trees and distant hills, enhancing the peaceful waterfront view.

Cottage in Onancock

Eastern Shore Romantic Waterfront Getaway Upscale

A waterfront getaway at the newly renovated Westview Cottage on Onancock Creek just off the Chesapeake Bay. Wake up to beautiful water views through floor-to-ceiling glass doors. A private, peaceful escape in the country conveniently surrounded by fields and wildlife complete with a dock for crabbing and fishing (seasonal) 4 MI to Downtown Onancock & Restaurants 4.5 MI to Walmart 25 Mi to Camp Silver Beach 35 MI to Chincoteague Island 39 MI to Cape Charles >save listing to your wishlist<<

4.94 out of 5 average rating, 115 reviews

An aerial view captures a secluded Victorian cottage nestled on a private island, surrounded by water and lush greenery. A footbridge connects the island to a winding path, merging into open fields and offering glimpses of the bay and forested areas in the distance.

Cottage in Hacksneck

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!

The kitchen features exposed brick walls and modern finishes. A wooden dining table with four chairs is positioned in front of a window, allowing natural light to illuminate the space. Stainless steel appliances are present, along with a large sink and ample counter space.

4.94 out of 5 average rating, 116 reviews

Bakery Next door! Beautiful Renovations

Nectarine 13 is centrally located, century old brick duplex is newly renovated and ready for guests. It's a short walk next door to the Coastal Baking Company to get your freshly baked cinnamon roll. Sit on the front porch and enjoy the calm, quaint, historic town of Cape Charles. Take a swim in the bay or cast your poles from the dock just blocks down Main Street. Central Park, is a short stroll, and a great place for a picnic while the kids enjoy the playground. Golf carts for rent as well.

4.87 out of 5 average rating, 302 reviews

Home in Grimstead

Gwynns Island Waterfront Getaway

Great cottage on the water with a fantastic view of the bay and best sunset on the east coast. Sliding glass doors make it feel like your on the water when your sitting on the couch or in the kitchen. You can crab, fish, kayak, grill out and swim right off the back deck. Very peaceful and relaxing. The newly renovated island restuarant is a mile away with a bar and bascically anything you would want to eat. My father left us the house, we use all the proceeds from Airbnb to make improvements.

4.96 out of 5 average rating, 103 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

4.98 out of 5 average rating, 308 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.

Tiny home in Cape Charles

A welcoming porch features a vibrant coral door framed by two windows. Light-colored outdoor chairs are arranged around a small table, complemented by a decorative mat and nautical-inspired decor. The covered area provides a cozy spot to relax outside.

4.88 out of 5 average rating, 118 reviews

Summer Camp Tiny Cottage Walk to the beach & shops

At less than 470 sq feet, this 1920s house is super fun & ready to be enjoyed for a couples, friends, and small families! • King sized bed with smart tv on the first floor • Two twin beds in a cozy sleeping loft • Small kitchen with propane stove, Nespresso maker & living space with a smart tv • Patio w/ charcoal grill, solo stove, & dining table • Paddle board & floats Please read through our totally honest disclaimer below!

5 out of 5 average rating, 18 reviews

A modern kitchen features white cabinetry and stainless steel appliances, including a refrigerator and oven. A spacious countertop offers room for food preparation. Natural light enters through the window, illuminating the neutral-toned flooring and decorative elements on the wall.

Condo in Tangier

The Tarryn Elizabeth Unit A

What better way to enjoy a getaway or family vacation than on a peaceful quiet island where the beach is clean and spacious and some of best fishing and crabbing in the world! Rent a four wheeler and drive on the beach 24/7 or lounge on the porch and soak in the sun, and not to mention the unlimited hi speed Internet with smart TVs in all 3 rooms for all your relaxing needs if you should choose to stay in the home!

4.8 out of 5 average rating, 108 reviews

Cottage in Cape Charles

Sea Salt Cottage: Tranquil Getaway 5 min to beach

Escape to the Eastern shore! Sea Salt Cottage is your quiet, off-the-beaten path getaway in charming Cape Charles. -Peaceful, rural feel with a 5 min drive to beach, quaint shops & restaurants. -Dog & kid friendly w/ large yard to park boats, RV's, etc. -Hammock, tree swing, outdoor dining, fire pit, romantic sunsets. -2 min to groceries, 10 min to Kiptopeake State Park, 70 min to Chincoteague Island

5 out of 5 average rating, 48 reviews

Captain's Cottage

The Captain's Cottage was originally built in 1886 and has recently undergone extensive renovations to create a home of charm, history, and comfort. Located a block away from Cape Charles's Central Park, four blocks from the beach, and two blocks from Mason Avenue, the Captain's Cottage is in a prime location in Cape Charles.

4.89 out of 5 average rating, 189 reviews

A modern kitchen and dining area is presented, featuring a large island with seating for four. An adjacent dining table accommodates four, with wicker chairs nearby. Natural light filters through multiple windows. The kitchen includes stainless steel appliances and white cabinetry, enhancing a clean and functional space.

Cottage in Gloucester

White Heron Cottage

Find yourself feeling cozy at this charming and peaceful home. Centrally located 15 minutes from our lovely little town and 45 minutes to Williamsburg, VA. Several public beaches are close by. Owners are proud Super Host who specialize in attention to detail and making sure guest have a great stay.

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Quaint homes, peaceful surroundings

Popular amenities for Cape Charles vacation rentals

Laptop-friendly workspace

Stay near Cape Charles's top sights

The Shanty65 locals recommend

Kelly's Gingernut Pub47 locals recommend

Cape Charles Brewing Company47 locals recommend

Cape Charles Beachfront40 locals recommend

Brown Dog Ice Cream38 locals recommend

The Oyster Farm Seafood Eatery34 locals recommend

House rentals in Cape Charles

4.91 out of 5 average rating, 109 reviews

Home in Buckroe Beach

3 bedroom home minutes from Buckroe Beach

4.87 out of 5 average rating, 78 reviews

A ranch-style home is presented, featuring a light-colored exterior with black shutters and a welcoming blue front door. A concrete pathway leads up to the entrance, surrounded by a grassy lawn. Mature trees and a wooden fence are visible in the background.

Home in Buckroe Beach

Home-Sweet-Home

A charming two-story house features white siding and a covered front porch. The entrance is highlighted by a pink door. A single chair is positioned on the porch, while a decorative flamingo adds a pop of color to the front yard, framed by neatly landscaped plants.

4.99 out of 5 average rating, 101 reviews

Palm Beach by the Bay

4.88 out of 5 average rating, 111 reviews

The image showcases a calm waterfront scene with several boats docked at a wooden pier. The surrounding marshland is visible in the background, under a clear blue sky with soft clouds, reflecting a serene coastal atmosphere.

Home in Wachapreague

Private House 4BR -Eastern Shore VA Wachapreague

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.

4.93 out of 5 average rating, 201 reviews

Charming house close to beach and shops!

4.89 out of 5 average rating, 36 reviews

Cape Cottage A (downstairs)

4.82 out of 5 average rating, 119 reviews

A comfortable living area is arranged with a sectional sofa featuring colorful cushions and a coffee table. A wall-mounted television is visible alongside a decorative clock. Artistic wall decor adds interest, while a dining table is set with light blue placemats and a vase of flowers.

Home in Buckroe Beach

Family, Friends, and Fun 3 Bdrm Beach Bungalow

4.88 out of 5 average rating, 114 reviews

Home in Exmore

House Sanctuary on the Chesapeake

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Vacation rentals with pools in Cape Charles

4.99 out of 5 average rating, 196 reviews

The Gothic Revival-style cottage is showcased from its charming exterior, featuring large arched windows and a welcoming front porch. Two wooden chairs sit invitingly on the porch, complemented by seasonal decorations. Surrounding trees provide a sense of tranquility within the peaceful setting.

Cottage in Irvington

Peaceful Haven: nature & charming town

Vacation home in Gloucester County

A vibrant sunset casts a warm glow over the water, with rich hues of orange, pink, and purple reflected in the calm surface. A dock extends into the scene, framed by grassy edges, contributing to the serene atmosphere along the river.

4.79 out of 5 average rating, 42 reviews

Waterfront 4 bedroom home with marina facilities

5 out of 5 average rating, 24 reviews

The exterior of a two-story house is shown, featuring a gray shingle facade and a welcoming front porch. Neatly trimmed shrubs and manicured lawns frame the driveway, while flowering plants add subtle color. A double garage with white doors is visible on the left.

Condo in Cape Charles

Bay Creek Blessed at The Fairways

4.89 out of 5 average rating, 117 reviews

A vintage pull-behind camper sits by the water's edge, featuring a striking teal color that contrasts with the clear blue sky. Grassy surroundings provide a natural setting, inviting views of the serene shoreline and distant water.

Camper/RV in White Stone

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

4.96 out of 5 average rating, 378 reviews

A charming gazebo is set beside a sparkling blue pool, surrounded by lush greenery and colorful flowers. The fenced area provides a sense of privacy, while the clear sky above creates a serene atmosphere. Sunlight reflects off the water's surface, enhancing the tranquil scene.

Apartment in Hampton

"Shangri-La", of Hampton, Virginia

5 out of 5 average rating, 68 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

4.95 out of 5 average rating, 112 reviews

A large outdoor swimming pool is nestled within a stone patio, surrounded by lush greenery and tall trees. Sunlight reflects off the clear blue water, while comfortable lounge chairs are positioned nearby, offering a relaxing space to enjoy the serene outdoor setting.

Barn in Cobbs Creek

The Barn at Pond Point - Riverfront Home

4.98 out of 5 average rating, 55 reviews

A comfortable seating area features a sectional sofa adorned with various cushions in soft colors. A white accent chair complements the arrangement. A large area rug with a wave pattern anchors the space, while a serene artwork depicting birds adds a touch of coastal charm.

Cottage in Cape Charles

Seabreeze Cottage ... explore the Eastern Shore!

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House rentals with pools in Cape Charles

4.99 out of 5 average rating, 177 reviews

Home in Gloucester Point

York River Vacation Home

A deck overlooks the tranquil waterway, with picturesque views of grassy areas and the shoreline. Brightly colored chairs provide seating options, while a wooden railing frames the outdoor space. The clear blue sky enhances the inviting atmosphere.

4.67 out of 5 average rating, 3 reviews

Hot Tub - Massage Chair - Golf Cart - Beach Gear

4.98 out of 5 average rating, 152 reviews

Home in Cobbs Creek

Blue Heron WaterSide

4.99 out of 5 average rating, 112 reviews

A refreshing swimming pool is visible, bordered by a concrete deck. Two charming structures resembling small cottages stand nearby, complemented by several white lounge chairs and vibrant umbrellas. Lush greenery surrounds the area, creating a serene backdrop.

Home in Irvington

The Rosé Retreat: Pool-Screened Porch-RELAX

A bright and inviting living area features a spacious navy sofa and two matching armchairs. A coffee table sits in front, while a wood-burning fireplace adds warmth. A flat-screen TV is mounted on the wall, and a staircase leads to the upper level. Light enters through large windows.

4.88 out of 5 average rating, 25 reviews

Sunshine Baydream Cape Charles

A clear blue pool is depicted, bustling with activity. A child is seen jumping into the water, wearing a safety vest. Surrounding the pool, a spacious deck provides ample room for lounging. A building is visible in the background, offering changing facilities and amenities.

4.92 out of 5 average rating, 79 reviews

Bay Creek (Pool!) Meets Historic Cape Charles!

4.99 out of 5 average rating, 136 reviews

A private hot tub is situated on a wooden deck surrounded by trees, offering a serene retreat. Sunlight filters through the branches, creating dappled shadows on the tub's surface. A wooden wall adds a rustic touch, featuring a decorative crab motif.

Home in Irvington

Escape to magical wooded cottage with hot tub