Holiday houses in Chesapeake

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Top-rated holiday rentals in Chesapeake

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite

Place to stay in Scarbro

5 out of 5 average rating, 118 reviews

Forest Glamping near NRG, Wildwood Flower-1 of 3

Your fully furnished luxury 16ft bell tent sits on a large elevated deck featuring a Solo Stove, Adirondack chairs, and hammock. To ensure ultimate seclusion, your site is located over 100ft from any other campers on our peaceful 16-acre property. It’s the perfect romantic getaway or place to unwind after a day of play in the New River Gorge National Park, which is only 20 minutes away. Your bell tent is fully powered, has AC, a heater, towels, and fresh bedding- all you have to do is show up!

FamilyValueParks

Guest favourite

A welcoming front entrance features a decorative sign that reads 'Welcome Americana Cottage' against a backdrop of a red door. A festive red, white, and blue fan decoration is displayed beside the door, adding a touch of American pride, complemented by a soft glow from an exterior light fixture.

Home in Charleston

4.95 out of 5 average rating, 177 reviews

Americana Cottage at Luna Park Historic District

You will be close to everything when you stay at this centrally-located home in Charleston’s Luna Park Historic District. Americana Cottage was built in 1920 at the cornerstone of the once renowned Luna Amusement Park. It boasts antique furnishings, cozy decor and a 2 level deck with fire pit. 2 blocks from the river. Within 10 minutes of all major hospitals, shopping, dining and entertainment, Americana Cottage is perfect for families, travel nurses and business travelers. A very unique stay!

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Guest favourite

The living room features a comfortable reclining couch and a bright red armchair, complemented by large windows dressed with yellow curtains. A colorful area rug covers the hardwood floor, while a small TV is set on a side table, providing a cozy space with natural light.

Home in Dunbar

4.99 out of 5 average rating, 161 reviews

River View Cottage

Keep it simple at this peaceful & centrally-located river cottage in Dunbar, WV. Enjoy the river view from this 2 bed/1 bath home updated and fully stocked for your stay. Convenient to the interstate, restaurants, shopping, hospitals & 1.5 miles from the Shawnee Sports Complex. We are 10-15 minutes from downtown Charleston, Mardi Gras Casino & Resort, Clay Center, Charleston Coliseum & Convention Center. We offer keyless entry and a home security system. Off-street parking. No pets allowed.

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Guest favourite

The exterior of the house is highlighted by a charming gabled roof and white clapboard siding. A stone chimney rises from the roof, and the entrance features a set of steps leading to a welcoming front door framed by large windows on either side, surrounded by lush green grass and trees.

Home in Charleston

4.89 out of 5 average rating, 334 reviews

Historic Farmhouse by Nature Preserve

We welcome you to The Little House, sensitively restored and thoughtfully furnished. Enjoy entire house and its 2.7 acres, adjacent to 52 acres of walking trails, while still in the heart of town. Ideal for nature-seekers and business travelers alike. Calm, quiet spot to read a book— or write one. (Please note price increase due to Airbnb fee inclusion). One loft bedroom with one full bed + one daybed. One pull-out loveseat downstairs; 2 stored iBeds. Re: pets: one dog allowed. No cats.

ValueFamilyGetting around

Guest favourite

The cottage's entrance features a wooden ramp leading to a blue door, framed by a gabled awning. Shuttered windows with decorative flower boxes enhance the welcoming atmosphere, while the light-colored siding and brown trim contribute to the cottage's charming exterior.

Cottage in Charleston

4.95 out of 5 average rating, 401 reviews

Peace Like A River

Freshly remodeled 2 bedroom cottage in North Charleston, West Virginia. Unwind with games, puzzles and books or take a hot bath in the claw-foot tub. You won't miss the TV when you can watch the sunset on the wrap around porch overlooking the Kanawha River. High-Speed Internet access is available to stay connected. You will be 10 minutes to The Charleston Coliseum and Appalachian Power Park. The Shawnee Sports Complex and WVSU are 7 minutes away. Come experience Peace Like a River!

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Guest favourite

A welcoming cottage exterior is framed by a green lawn and mature trees. The house features a peaked roof and a combination of brick and textured siding. A covered front porch, adorned with a wreath, invites guests to enter. Surrounding homes and a fence are visible in the background.

Home in Charleston

5 out of 5 average rating, 11 reviews

Charming Charleston cottage

Welcome to this charming, newly renovated cottage in the heart of Charleston! This peaceful retreat is just minutes from CAMC and WVU hospitals, downtown shops, restaurants, and the State Capitol. Perfect for traveling nurses, professionals, or couples looking to explore the area. This cozy home offers an inviting living space, a fully equipped kitchen, and two comfortable bedrooms. Enjoy the beautiful tree-lined streets and unwind on the back patio after a day of work or adventures.

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Guest favourite

A serene pond is surrounded by lush landscaping and illuminated with twinkling lights. The soothing water features a gentle fountain in the center. An old car rests on the shore, adding a unique vintage touch to the peaceful outdoor atmosphere.

Guest suite in Charleston

4.89 out of 5 average rating, 175 reviews

Retreat in the mountains with new hot tub & deck.

Located in Charleston,WV near CAMC Memorial Hospital. 10 minutes away from Yeagar Airport.This fully furnished basement has recently been remodeled which provides a quiet and clean space to relax or work. King size bed and queen size pull out sofa. Air mattresses available. Two full baths. Brand new hot tub. Jacuzzi tub. You can relax and unwind on the deck while over looking the pond and waterfall. At night you can take a leisurely walk around the pond under the lights.Free Wi-Fi.

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Top Guest favourite

A modern front door is opened wide, inviting guests into the home. A welcome mat featuring the phrase 'WELCOME HOME' is visible on the doorstep. Light-colored flooring can be seen inside, along with a glimpse of decor and furnishings.

Home in Charleston

5 out of 5 average rating, 208 reviews

The 505 on Margaret

Welcome to our custom-built brand-new house in the heart of Charleston West Virginia. This house was completed June 2024 and has been furnished, stocked, and designed with the most modern and updated materials. We have specifically designed this house for nightly, weekly or month-long stays. Located 2 blocks from the Charleston Coliseum and a short walk to the lively capitol street. Check out our other house next door to this one, The 314 on Joseph. Children and pets are welcome.

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Guest favourite

A two-story log cabin is nestled among lush greenery, featuring a welcoming front porch with wooden railings. Large windows allow natural light to fill the interior, while a gravel path leads up to the entrance. The surrounding trees provide shade and a sense of privacy.

Cabin in Charleston

4.99 out of 5 average rating, 118 reviews

Naughty Pines *ADULT ONLY* NEW

This unique adult themed two bedroom/two-bathroom log cabin is centrally located in Charleston, WV. We offer custom designed spaces for consenting couples to explore or indulge in new desires. Our cabin has a private hot tub and fire pit area for couples to enjoy. We offer a custom made BDSM bed, St. Andrew's Cross, leather swing, medical exam table, sex chair and queen size bed for sleeping. Our cabin is designed to help couples reconnect, relax and explore new things.

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Guest favourite

A serene creek meanders through a landscape covered in fallen leaves, surrounded by bare trees. The ground is blanketed in brown foliage, creating a natural setting that highlights the tranquility of the rural area. The water is partially obscured by the leaf litter.

Farm stay in Spurlockville

4.95 out of 5 average rating, 107 reviews

Horse Creek - Cardinal Cabin Near Ivy Branch HMT

This cabin built in 2022 includes all modern amenities with a beautiful wooden design. Located about 4 miles from the Hatfield McCoy Trails Ivy Branch location and lots of room to park then ride your side by side directly to the trails. Also close to the former Hobet Mine. A very peaceful and beautiful rural area with lots of wildlife around such as deer and turkeys. Relax by the fire pit or walk down to the creek. Only a 25 minute drive from the Southridge Shopping Center.

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Guest favourite

Cottage in Fayetteville

4.89 out of 5 average rating, 209 reviews

Riverfront Cottage on the New River Dries

Imagine kayaking or SUPing the New River right out from the back yard. Maybe you prefer sitting by the water fishing for your dinner. Or relaxing by the water watching the sunset as a lonesome train whistle echoes across the water. This cozy riverfront cottage, right on the New River, offers all levels of recreation & relaxation. Fayetteville & the New River Gorge is a 20-25 minute stunning, scenic drive. Enjoy all that the area has to offer from this lovely rent

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Top Guest favourite

An outdoor sitting area is visible on the houseboat, featuring comfortable wicker chairs and a dark table. Soft lights illuminate the space, with the reflection of the State Capitol's dome seen in the water. The scene captures a serene evening ambiance.

Houseboat in Charleston

4.95 out of 5 average rating, 117 reviews

Camp David, Charleston’s Ultimate Experience!

One of a kind experience .. Located on the Kanawha River with stunning views of the State Capitol. Camp David offers the sights, sounds and relaxation that being on the water brings. Our rental comes with the complimentary use of bikes, kayaks, SUP’s when available and an add on option of a pontoon sightseeing or to take the boat to brunch, lunch or dinner and enjoy the sunrise, sunsets or the beautiful views of the mountains.

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