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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Superhost
Apartment in Huntington
4.87 out of 5 average rating, 182 reviews

Boutique Aparthotel: Terrific Teal w/Spa Touches

This remodeled space blends modern comforts with original 1911 character. ✨Amenities include a water feature, towel warmer, bath robes, white noise machines ✨ Features the original 1911 cast iron tub, bathroom tile, and hardwood floors ✨Relax on the expansive covered balcony or explore downtown. ✨ Centrally located, you’re steps from restaurants, grocery stores, and shops, with quick access to Marshall U, hospitals, and parks. ✨Dining area can be used as 3rd bedroom! 👶 High chair, mini crib

Guest favorite
A wooden picnic table is set in a snowy area, adjacent to a gently flowing waterfall. Surrounding trees are bare, and rocky cliffs rise in the background, partially covered by snow. The scene conveys a serene natural setting.
Home in South Point
4.94 out of 5 average rating, 105 reviews

Secluded 75 ac Home, families /horses allowed

Secluded (dead end of the road ), tons of wildlife (deer, turkey and more) Several waterfalls on property! Tri-state area includes Ohio, West Virginia and Kentucky…house is 15mins from all 3! Sleeps 12-14 6 bedrooms , 2 1/2 baths , couch/queen bed in additional room off kitchen. and a couch in the living room. Property is on 75 acres with barn. One of the waterfalls has a picnic area and bridge. Great Retreat property…camping, fields for sports, youth retreats… endless versatility options.

Guest favorite
An open concept living space features a sectional sofa with a coffee table, offering floor-to-ceiling windows that showcase city views. Modern kitchen appliances and a dining area with seating are visible. Sleek light fixtures enhance the welcoming atmosphere.
Loft in Ashland
4.95 out of 5 average rating, 384 reviews

Sky Loft on 10 . 2 bed . 2 bath + Modern luxuries

Lay your head in the clouds. Sky Loft on 10 is a brand new, state-of-the-art loft furnished with modern luxuries. It is conveniently located in the center of the city blocks away from downtown, Paramount Arts Center, KDMC, Central Park and the Ashland Town Center Mall. Tenth floor views and access to two private balconies provide stunning views of the city, riverfront and Tri-State area. Perfect for hosting or a relaxing getaway. Your next stay, retreat or celebration is just on the horizon.

Top guest favorite
A cozy living area is highlighted by a gray armchair positioned near a decorative stone fireplace. A television is mounted above the mantle, and a small dining table is visible nearby. Natural light is softly filtered through sheer curtains.
Home in Huntington
4.98 out of 5 average rating, 102 reviews

The cozy cottage

The cozy cottage is on the south facing slope in the foothills of the Appalachian mountains. It’s .5 mile from I-64 but feels much more rural than the convenient 7 minute drive to downtown Huntington. Its location on the outskirts of the city makes for nice relaxing evenings with the convenience of still being close. The master bedroom has a tv and queen size bed. The spare bedroom has a tv and full size bed. The living room has a tv, dvd player, and queen size pull out sleeper sofa.

Guest favorite
A spacious two-story home is set in a lush, green landscape. The exterior features white siding with blue shutters and a symmetrical arrangement of windows. A welcoming front porch is complemented by neatly trimmed shrubs and trees, while a two-car garage is visible on the right.
Home in Barboursville
4.91 out of 5 average rating, 230 reviews

Mountain State Getaway | 6BR • Sleeps 16+

Why book separate hotel rooms when your group can stay together? Mountain State Getaway offers approximately 4,000 sq. ft. with 6 bedrooms and 3.5 bathrooms—ideal for families, reunions, wedding groups, sporting events and Marshall visits. Enjoy spacious kitchen and dining areas, multiple gathering spaces, a game room, sunroom and large furnished deck with grill. Located in a quiet Barboursville neighborhood near dining, shopping, Barboursville Park, Huntington and Marshall University.

Top guest favorite
The living room features dark green walls that frame a cozy space. A fireplace with a decorative screen sits centrally, surrounded by built-in shelves. A wooden chair and a modern orange chair offer seating options, with a colorful area rug adding warmth to the hardwood floor.
Home in Huntington
4.98 out of 5 average rating, 133 reviews

Charming 2BR Home - Marshall U & Local Attractions

Welcome to our charming 2BR Huntington home, perfect for 4 guests! Enjoy modern comforts: Wi-Fi, 50-55” Roku TVs, and a fully equipped kitchen with a unique 48" gas range. Relax in our cozy living space with an electric fireplace, or explore the area, minutes from Marshall University, local parks, and attractions. Our pet-friendly home features a quaint front porch, fenced backyard, and convenient parking. Experience local charm, modern amenities, and easy access to Huntington's best!

Guest favorite
A cozy kitchen area is visible, featuring wooden cabinetry and a counter space with two iron bar stools. Natural light enters through a window, highlighting the inviting atmosphere. An adjoining door leads to the entrance, while a simple lamp and decorative items enhance the space.
Guesthouse in Huntington
4.95 out of 5 average rating, 1099 reviews

Cozy 1 bedroom small house/apt

Welcome ! We are within short driving distance to: Marshall University, Cabell Huntington Hospital or St. Mary's, the Huntington Mall. The apartment is small, quaint and cozy, offers a full kitchen, & comfy bed. Because we live close to a highway and railroad, there is some traffic noise at times. Our driveway parking is inclined, and we are also located on a bus line. The Wi-Fi is ready & this a pet-friendly stay! 🐶 Voted Most Desired AirBnB in Huntington in 2018!

Top guest favorite
The exterior of the guesthouse is displayed, featuring a wooden deck with steps leading up to a door. Soft evening light highlights the structure's features, including the metal roof and large windows with sheer curtains. Trees border the area, enhancing the natural setting.
Guesthouse in Huntington
4.94 out of 5 average rating, 266 reviews

Entire Guesthouse 2 minutes from I-64

Hello, Our guest house is very private, quiet, cozy, secure and exceptionally clean. A great couples retreat with 2+miles of hiking trails and a vast space for outdoor activities and wildlife viewing. The beds are comfortable and the heat and air conditioning are great. We have all the amenities...all linens are furnished. There is a washer, dryer, iron and hair dryer and detergent. We are nestled on over 100 acres of land and are 1000 feet from the nearest highway.

Superhost
A cozy hilltop home is framed by tall trees, set against a backdrop of a warm sunset. The large yard is visible, complemented by a gravel driveway leading to a spacious garage. The tranquil scene offers a sense of serenity in a peaceful setting.
Home in Huntington
4.9 out of 5 average rating, 49 reviews

Cozy Hilltop Cottage

Welcome to your hilltop haven—where peace and quiet meet easy access. This cozy home sits in a quiet neighborhood with a big yard and country feel, just 5 minutes from I-64. Perfect for travelers looking to relax, families needing space, or anyone wanting a calm retreat with quick access to local shops, dining, and attractions. Enjoy starry nights, morning coffee on the porch, and the simple comforts of home while still being less from 10 minutes from downtown Huntington.

Top guest favorite
Home in Huntington
5.0 out of 5 average rating, 33 reviews

The Park House A 5 Bedroom Retreat w/Game Room &

Step into luxury at The Park House by Nest & Bloom Properties - a newly renovated 100-year-old home in Huntington, West Virginia. This 5-bed, 3.5-bath retreat sleeps 10 and features a designer kitchen, game room, formal dining room, and modern updates throughout. Unwind by the fire pit or stroll to Ritter Park. Minutes from downtown, hospitals, and Marshall University - perfect for elegant stays with timeless charm. 🌿

Top guest favorite
Townhouse in Chesapeake
4.94 out of 5 average rating, 66 reviews

2BR 1.5 BA Townhouse with Riverviews

Location, Location, Location! Close proximity to St. Mary's/Cabell/Huntington hospitals, Three Gables Surgery Center, Marshall University, Marshall Health Arena, shopping, etc. while being outside of the city. Located between Chesapeake and Proctorville, Ohio. 5 minutes to downtown Huntington. 25 minutes to downtown Ashland, KY and Sandy's Casino. Relax on the back decks and enjoy the views of the Ohio River.

Top guest favorite
Apartment in Huntington
4.92 out of 5 average rating, 186 reviews

Frontier Suite at St. George Flats

Newly updated! Welcome to the Frontier Suite—a freshly renovated 1-bed retreat featuring cozy Western-inspired decor and rustic charm. Located on the first floor with a private entrance, this unit offers a bright living room, dedicated dining area, full kitchen, and a restful bedroom with rustic accents. Enjoy modern comforts, stylish finishes, and a character-rich stay designed for complete relaxation.

Popular amenities for Chesapeake vacation rentals