Vacation rentals in Chesapeake

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Top-rated vacation rentals in Chesapeake

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

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Top guest favorite
A charming white house is nestled among vibrant autumn trees, showcasing a blend of red, orange, and green foliage. The building features a pitched roof and two gabled windows, with a front door flanked by outdoor lighting fixtures, leading to a set of steps.
Home in South Hills
4.89 out of 5 average rating, 326 reviews

Historic Farmhouse by Nature Preserve

We welcome you to The Little House, sensitively restored and superbly 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 environs in which to read a book— or write one. One loft bedroom with one full bed + one (30" x 70") daybed. One pull-out loveseat in sitting room; 2 stored iBeds. Note all bedding details under Space. Re: pets: one dog allowed. No cats.

Top guest favorite
The exterior of a renovated 1950's house features a welcoming front porch with hanging plants and seating. The entrance is marked by a dark door beneath a covered awning, with steps leading up from a grassy area. A sign identifies the property as 'Hamilton House'.
Cottage in Ansted
4.92 out of 5 average rating, 162 reviews

Hamilton House

1950's renovated house with lots of original character next to Hawks Nest State Park and close to 2 more State Parks, in a quiet neighborhood and within a few minutes to all the New River Gorge National Park has to offer. 15 minutes from historic Fayetteville and the New River Gorge Bridge, central to whitewater rafting and rock climbing companies. We have 3 outdoor spaces and a bbq area. Our covered deck is 18' long and has a picnic table and other seating and the front porch has a nice swing

Top guest favorite
A fully furnished bell tent sits on a spacious wooden deck surrounded by lush greenery. An inviting hammock is suspended nearby, and the forested area features a natural landscape with scattered leaves and tree trunks, creating a serene outdoor atmosphere.
Place to stay in Scarbro
5 out of 5 average rating, 118 reviews

Forest Glamping, Blackberry Blossom-2 of 3

Be surrounded by nature in ultimate comfort. Our 16 acre property is the perfect romantic getaway or place to unwind after a day in The New River Gorge National Park. Your fully furnished 16ft bell tent was tastefully designed with you in mind. You’ll enjoy a large deck with Solo stove, and your site is located over 75ft from any other campers. Since your tent has power, AC, a long list of amenities, like towels and bedding, all you have to do is show up! Snag the hammock, kick back and relax.

Guest favorite
A charming blue cottage is positioned near the river, showcasing large windows that provide natural light. The surrounding greenery includes trees and a grassy area. A picnic table is visible in the foreground, with a view of the bridge spanning the water in the background.
Home in Dunbar
4.99 out of 5 average rating, 148 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.

Top guest favorite
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, 386 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!

Top guest favorite
A balcony overlooks the serene Great Kanawha River, featuring a table and two chairs arranged for relaxation. The railing provides a secure boundary, while the clear sky enhances the natural surroundings.
Home in South Charleston
4.99 out of 5 average rating, 137 reviews

The Riverbend Retreat | Riverfront Home

Relax by the riverside with this stunning, amenity-packed location! This fully remodeled 2 bedroom home will be perfect for a couple's getaway or a family trip. Enjoy beautiful views of the Great Kanawha River, downtown shopping in the Charleston area, or take the scenic drive to the New River Gorge for even more adventures! Our pet-friendly property has all the comforts of home, with the bespoke style of a luxury stay. Come and experience the Wild and Wonderful beauty of West Virginia!

Guest favorite
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
4.9 out of 5 average rating, 165 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.

Top guest favorite
Home in Charleston
4.99 out of 5 average rating, 190 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.

Top guest favorite
Apartment in Kanawha City
4.97 out of 5 average rating, 174 reviews

Enjoy our Cozy Garage Apartment

You will love staying in this one bedroom garage apartment, located in the neighborhood of Kanawha City, in the south east section of Charleston , West Virginia. Situated on the Kanawha River, we are minutes from grocery stores and restaurants. We are less than 10 miles from downtown Charleston which has a lot to offer in cultural experiences and locally owned restaurants and businesses. Enjoy the neighborhood feel and enjoy the view of the mountains and the beautiful river.

Top guest favorite
Loft in Charleston
4.93 out of 5 average rating, 364 reviews

The BearBnB - Pet friendly, 5 mins to downtown

Take it easy at this almost heaven hideaway. This adorable, Bear themed loft gives you the country setting you’re looking for and the convenience you need. Located just 5 minutes from downtown Charleston and Yeager Airport. Enjoy the peace and quiet of nature or hop downtown for an array of shopping and eatery selections. Tour the West Virginia State Capitol topped with its gorgeous gold dome or dive into WV’s many adventures. Business or pleasure, you’ll love the Bear BNB

Guest favorite
Cabin in Charleston
4.95 out of 5 average rating, 171 reviews

Rosie's Cabin

Rosie's Cabin is located just 10 minutes from downtown Charleston. Our cabin is an authentic log cabin that is spacious and offers plenty of room to spend time with family and friends. The cabin sits in a peaceful neighborhood located just outside City limits. Rosie's offers a hot tub, fire pit, wood burning fireplace, charcoal grill and plenty of shared parking space with nearby cabin. ** Winter months may require a four wheel drive vehicle due to driveway. **

Guest favorite
Apartment in Charleston
4.95 out of 5 average rating, 126 reviews

A Royal Hideaway-Serene Feel Apt In Charleston, WV

Conveniently located near a TESLA CHARGING STATION! This newly remodeled condo style apartment is conveniently located in the heart of downtown. The location is in walking distance to some of the best restaurants, shopping, and more. Just steps away from the Clay Center and CAMC General Hospital for nurses. Staying here you definitely get to experience what it’s like to live downtown and see what all beautiful Downtown Charleston has to offer!

Popular amenities for Chesapeake vacation rentals