
Holiday houses in Chesapeake
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Chesapeake
Guests agree: these stays are highly rated for location, cleanliness and more.

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 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 downstairs; 2 stored iBeds. Note all bedding details under Space. Re: pets: one dog allowed. No cats.

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!

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.

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.

2 Bed, 1 Bath - King Bed - Garage available - W/D
Hi, my name is Kevin. My wife and I have been running this Airbnb for the past two years. Please send me your questions if you have them. Thanks, Kevin Info you need to know + 2 bed, 1 bath + extensions available + Discounts available for stays of 4 months or more + King bed, Queen bed + Dishwasher + Washer and Dryer + Garage space + Carport Location + 2 minutes to the Grocery store + 5 minutes to the Interstate + 2 minutes to the Bank + 10 minutes to the Casino + 3 hours to Columbus, OH

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!

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.

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.

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 boat rental. When the captain is available, there’s an option to take a pontoon ride to brunch, lunch or dinner and enjoy the sunrise, sunsets or the beautiful views of the mountains.

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.

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.

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
Popular amenities for Chesapeake holiday rentals
Other great holiday rentals in Chesapeake

Charming Charleston cottage

Country Domes, Take Me Home!

New! Rustic Creekside Cabin-Hot Tub, Cozy, Private

Downtown Retreat Spacious & Equipped

Minutes from Downtown Charleston & game room

Completely renovated for you Mountain View Cottage

Angels Haven - Hot Tub, Game Rm, King Bd, Peaceful

Secluded mountain getaway with hot tub & view
Destinations to explore
- Sevierville Holiday rentals
- Washington Holiday rentals
- Charlotte Holiday rentals
- Gatlinburg Holiday rentals
- Pigeon Forge Holiday rentals
- Indianapolis Holiday rentals
- Pittsburgh Holiday rentals
- Columbus Holiday rentals
- Asheville Holiday rentals
- Cleveland Holiday rentals
- Louisville Holiday rentals
- Raleigh Holiday rentals





