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Holiday houses in Chesapeake

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Top-rated holiday rentals in Chesapeake

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Top 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 South Hills
4.89 out of 5 average rating, 323 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 favourite
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, 112 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 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, 136 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 favourite
A serene outdoor space features a cozy swing and glowing string lights, illuminating the deck overlooking the river. The area is complemented by a fire pit with seating and chairs arranged for leisure. Lush greenery and mountains create a tranquil backdrop.
Cottage in Boomer
4.98 out of 5 average rating, 221 reviews

Riverfront w/ Deck - Dock - Pets - Fire-pit & View

Cozy 3-bedroom riverfront cottage in Boomer, WV offers a large deck w/ stunning river views and a private dock for anglers, boats/jet skis, and easy access for kayaks, canoes, tubes, paddleboards. Relax around the firepit or enjoy the spacious fenced-in yard, perfect for kids and pets. Located roughly 30 min. from NRG National Park & Charleston. 40 min. from Summersville Lake & Rail Explorers in Clay. Book your stay today for a peaceful riverside retreat in beautiful WV. NO CLEANING FEE

Top Guest favourite
Sunlight filters through the trees, illuminating the outdoor space featuring a gravel patio, a fire pit surrounded by stone seating, and a wooden bench with potted yellow flowers. The cabin's screened porch and large deck are visible in the background.
Cabin in Fayetteville
5 out of 5 average rating, 164 reviews

Cozy Cabin minutes from NRG National Park

Emerson and Wayne is a quaint, luxurious, newly constructed cabin. Located just 10-15 minutes from everything Fayetteville and the NRG National Park have to offer. The ideal location if you're looking to get away from the hustle and bustle of it all yet still want to explore the beauty and adventures of our town/state. Very private, with the entire cabin and property to yourself. Enjoy relaxing on the decks or soaking in the hot tub while listening to the peaceful sounds of nature.

Top 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
4.92 out of 5 average rating, 153 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 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, 170 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 favourite
The kitchen features white cabinetry and appliances, including a refrigerator, stove, and oven. A small round table with two metal chairs is positioned near a window, dressed in light curtains. A decorative bowl of fruit adds a pop of color on the table.
Apartment in Kanawha City
4.96 out of 5 average rating, 165 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.

Guest favourite
The exterior of a guesthouse is framed by vibrant autumn foliage. A two-car garage is present, with a staircase leading to the entrance. A black bear-themed decoration sits in front, adding a charming touch to the natural surroundings illuminated by warm sunset light.
Guesthouse in Charleston
4.93 out of 5 average rating, 345 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 favourite
A welcoming porch is featured, adorned with wooden railings and a dark overhang. Steps lead up to the entrance, surrounded by natural greenery. A small table and chairs are located on the porch, offering a space to enjoy the outdoors.
Cabin in Charleston
4.95 out of 5 average rating, 154 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. **

Top Guest favourite
A softly lit cabin stands beneath a full moon, surrounded by trees. A wooden walkway with glowing green lights leads to the entrance, inviting guests to explore. The atmosphere is enhanced by warm lights on the cabin's exterior, creating a serene evening setting.
Tiny home in Summersville
5 out of 5 average rating, 126 reviews

Mystic Pond Cabin-Dark History!

Tiny house/big personality! Stay on our 350 acre farm where Bigfoot sightings & dark history have occurred. Intriqued by the paranormal? We provide ghosthunting gear for your visit. Cozy private cabin is nestled under old trees in a mountain valley on a reclaimed coal mine site. 30 minutes to New River Gorge National Park. 20 minutes to WV Bigfoot museum. 10 minutes to Summersville Lake. 5 minutes to a Winery and Distillery. Walk our farm trails, relax & stargaze.

Top Guest favourite
A studio apartment features a queen-size bed with a vivid orange comforter, complemented by two orange chairs and a writing desk. Natural light enters through two windows adorned with red curtains, and a decorative area rug enhances the space's warmth.
Apartment in South Charleston
4.99 out of 5 average rating, 162 reviews

An All-Access Bookstore Vacation

Ever thought of having your own bookstore? Here's your chance to live that dream! Plot Twist Books is a charming independent bookshop just minutes from West Virginia's capital city. With our attached studio apartment, you can explore the bookshop 24/7 while learning a bit about the bookselling business. This rental is designed for people who want to go “behind the shelves” at a true independent bookstore.

Popular amenities for Chesapeake holiday rentals