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
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, 327 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.

Guest favorite
Apartment in Cross Lanes
4.97 out of 5 average rating, 148 reviews

SWEET Storage Unit!

Have you ever wondered what it would be like to stay overnight in a mini storage? Probably not, lol! But if you’ve ever watched HGTV, you’ll see that people across the country are creating short term rentals out of all kinds of crazy things from shipping containers and barns to old warehouses and yurts. In Cross Lanes, WV, we took our cues from those folks on TV and created a short term rental out of the storage unit! Conveniently located just off I 64 and only 1 mile to the Mardi Gras casino.

Top guest favorite
A wooden cabin with a red metal roof is nestled among lush greenery, surrounded by trees and a manicured lawn. A gravel driveway leads to the cabin, with a vehicle parked nearby, enhancing the welcoming atmosphere of the outdoor space.
Home in Lansing
4.93 out of 5 average rating, 243 reviews

~1mi to NRG Bridge. Borders National Park. Hot tub

Returning guests request a discount! 1 mile to New River Gorge National Park Canyon Rim Visitor Center and NRG Bridge, with immediate access to a main road; bordering the NP, and only a few minutes drive to Fayetteville and Oak Hill. An outdoor hot tub on a patio balcony overlooks the spacious yard and forest edge. Campfire area with charcoal grill. Roku TV and fast WiFi inside. Price based on 2 guests; increases per person, per night for 3 or more people (waived for stays of a month or more).

Top guest favorite
Place to stay in Scarbro
5 out of 5 average rating, 100 reviews

Forest Glamping, Wildwood Flower-1 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 100ft 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
Cottage in Charleston
4.88 out of 5 average rating, 265 reviews

Hunt Cottage-3 Miles from Downtown Charleston

Charming, remodeled private cottage completely surrounded by West Virginia nature! No neighbors in sight and less than 2 miles from I-64. Enjoy the peace and quiet of a cottage in the mountains only 3 miles from all bars, restaurants, and entertainment! Convenient to: CAMC General (2.5 miles) CAMC Memorial (5.3 miles) Thomas Memorial (7.7 miles) Airport (6.6 miles) Charleston Coliseum and Convention-Center (2.1 miles) University of Charleston (6.1 miles) Mardi Gras Casino (14 miles/20 minutes)

Top guest favorite
A view from the wrap-around porch captures the serene landscape overlooking the Kanawha River. The scene features trees with autumn foliage, a grassy area, and a gentle sunset illuminating the horizon.
Cottage in Charleston
4.95 out of 5 average rating, 388 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
Home in South Charleston
4.99 out of 5 average rating, 140 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.

Guest favorite
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, 106 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.

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 Glen Jean
4.9 out of 5 average rating, 156 reviews

The Green Cabin at Wood Mountain Campground

The Green Cabin. In the heart of the New River Gorge recreation area of West Virginia, we are minutes from I-64/I-77, Beckley and the small town of Fayetteville that is easy to fall in love with. Our cozy 2 BR cabins are brand new, very clean, big front porches, great decor, fully furnished including a kitchen, fire pits, and 5 acres of campground space. Convenient to whitewater rafting, hiking, historical sites, national and state parks, great local restaurants and more!

Top guest favorite
Home in Charleston
4.91 out of 5 average rating, 101 reviews

Spacious Suite ·Peaceful Deck ·WiFi ·Near Downtown

Relax, unwind, reconnect at Ravinia Road Retreat. Our cozy, mid-century modern home features a spacious rear deck, fire pit, and smart TVs in every room. Explore historic Charleston or nearby shops & restaurants (minutes away). Unwind by the electric fireplace in your private suite with a spacious walk-in shower or relax by the fire pit on the inviting back deck with friends. Whatever your occasion, Ravinia Road Retreat is your destination.

Popular amenities for Chesapeake vacation rentals