Holiday rentals in Chesapeake

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Top-rated holiday rentals in Chesapeake

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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 South Hills
4.89 out of 5 average rating, 316 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 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 West Side
4.96 out of 5 average rating, 143 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!

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, 120 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 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, 110 reviews

Mystic Pond Cabin-Dark History!

Tiny house/big personality! Stay on our farm where Bigfoot sightings & dark history have occurred. Intriqued by the paranormal? We provide ghosthunting gear for your visit. Cabin is nestled under old trees in a mountain valley on a reclaimed coal mine site. Fish the spring-fed pond in warm months. 4 Rockers on front porch perfect for coffee & cocktails.Walk farm trails, relax & stargaze. 5 mins to Summersville Lake, 20- West Virginia Bigfoot Museum, 30-New River Gorge National Park, 45-TALA.

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, 145 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
4.91 out of 5 average rating, 140 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, 141 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.
Flat in Kanawha City
4.96 out of 5 average rating, 150 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.

Superhost
A serene river view is captured, featuring the tranquil water flowing beside a grassy area. Lush green trees line the bank, complemented by a mountainous backdrop, creating a peaceful natural setting.
Home in Belle
4.91 out of 5 average rating, 162 reviews

River Retreat,LLC/4.5 m to Charleston/River access

Unwind in the serenity of this beautiful home, situated in the heart of the Appalachian Mountains, where you can gaze at the breathtaking Kanawha River and mountainous backdrop from the comfort of a covered patio. Includes access to the river for fishing or kayaking (gear not included). Minutes away from historic Charleston, offering a balance of access to city attractions with a scenic place to rest after adventuring. Close to Interstates 64, 77, and 79. No cleaning fee.

Superhost
An all-terrain vehicle is parked on a gravel area beside a classic wooden cabin. The cabin features a set of steps leading to the entrance. Sunlight filters through bare trees in the background, highlighting the natural outdoor setting.
Cabin in Clendenin
4.88 out of 5 average rating, 106 reviews

RealTree Camo Cabin 2 - Amish Built Classic WV

This classic WV cabin has everything you need for a comfortable escape. There is a queen bed and a pull out Twin XL. There is another Twin XL matress in the closet if needed. The kitchen is ready for chefs! A nice laundry room and bathroom also. Outside the cabin door you can sit on a bench and enjoy a fire, roast marshmallows and enjoy the scenery. Firewood is provided. Inside the cabin guests can enjoy 2 flat screen tvs plus a DVD collection. This cabin has heat & air.

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
4.96 out of 5 average rating, 135 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 modern living area features a gray sectional sofa adorned with yellow decorative pillows. A white coffee table is positioned in front, and a built-in shelving unit displays colorful decor items. A dining area is visible in the background, showcasing a round table and chairs.
Apartment in Charleston
5 out of 5 average rating, 200 reviews

Trier Loft at Renaissance Tower

Trier Loft is a luxury downtown condominium located on picturesque Capital Street in Charleston, WEST VIRGINIA. It is in a 100+ year old building that was originally the KB&T Building. There are spectacular views of Charleston and its surrounding hills from its 5th floor vantage point. It is within easy walking distance to Charleston's most popular restaurants, bars, theaters, specialty shops, and concert venues.

Popular amenities for Chesapeake holiday rentals