Vacation rentals in Chesapeake

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Top-rated vacation rentals in Chesapeake

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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, 313 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

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

4.94 out of 5 average rating, 298 reviews

The Bear BnB - 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 just 3 minutes from 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 WVs many adventures. Business or pleasure, you’ll love the Bear BNB.

Top guest favorite

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 Charleston

4.96 out of 5 average rating, 133 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!

Top guest favorite

A welcoming living area features a cozy sofa, a modern coffee table, and a stylish chair. A wooden dining table for two is positioned nearby. Natural light fills the space, highlighting the textured carpet and neutral wall tones, with a decorative bowl resting on the coffee table.

Guesthouse in Dunbar

4.97 out of 5 average rating, 155 reviews

River view apartment for 1-2 guests

Updated with comfort and security in mind. This 1 br/1 bath unit is a river-front property with a calming river-view from the desk area. The space offers a galley kitchen with a gas stove, microwave and toaster oven. The bedroom has a queen memory foam mattress and black-out curtains. In the living room, there is ample seating, a work area, and smart tv. The bathroom and laundry areas are updated to offer all of the amenities that one would expect. Wi-fi and self check-in with smart lock.

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

4.94 out of 5 average rating, 349 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!

Guest favorite

A rustic cabin exterior is framed by trees, featuring a wooden porch with steps leading to a front door. Firewood is stacked neatly beside the entrance, while the surrounding area showcases a grassy patch and natural ground cover.

Cabin in Clendenin

4.92 out of 5 average rating, 109 reviews

RealTree Camo Cabin 3

This cabin is rustic and small but super cozy! It's comfortable with a queen size bed, a wood burning stove, air conditioning, fridge freezer, coffee, creamer & sugar provided, a smart tv & more. The creek runs in front of it and is literally up against a mountain, surround by mountains. This cabin is located right beside the shower house. There are beautiful hiking trails, a coal mine is a short hike away and a secret wilderness chapel. Enjoy some simple time up & away from town life.

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

4.91 out of 5 average rating, 129 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

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, 124 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.

Guest favorite

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, 143 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 favorite

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

4.97 out of 5 average rating, 121 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 gravel driveway. **

Guest favorite

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

4.92 out of 5 average rating, 157 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.

Guest favorite

The open-concept kitchen features modern appliances and a central dining island with seating for four. Light floods in through large windows, highlighting the sleek cabinetry and tasteful décor. A cozy lounge area is partially visible, adding to the comfortable atmosphere.

Condo in Charleston

4.93 out of 5 average rating, 174 reviews

Cozy Family Apt In Downtown 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!