
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.

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
4.87 out of 5 average rating, 182 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.
4.94 out of 5 average rating, 107 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.
4.95 out of 5 average rating, 386 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.
4.98 out of 5 average rating, 104 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!
4.98 out of 5 average rating, 134 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!
4.95 out of 5 average rating, 1100 reviews
Huntington Modern History - 4BD, MU, DT, St Mary's
Step into a perfect blend of historic charm and modern comfort in this beautifully updated 1920s home. Located just 1 mile from Marshall University and Joan C. Edwards Stadium, 1/2 mile from the Soccer Complex and St. Mary's Medical Center, this 4BR retreat is ideal for families, professionals, and sports fans alike. Whether you're here for a game, a visit, or just passing through, we invite you to settle in and enjoy the warmth and convenience of this updated historic home.
4.95 out of 5 average rating, 43 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.
4.94 out of 5 average rating, 267 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.
4.9 out of 5 average rating, 50 reviews
The Crane's Nest on Crane Ave in Huntington, WV.
Enjoy a relaxing stay with the whole family in this small, quiet residential area. Conveniently located off the 29th Street exit of I-64, between Huntington—home of Marshall University—and the Huntington Mall. WE are ten minutes from the center of the City of Huntington and only 5 minutes from St. Mary's Medical Center. Ideally situated for events in the tri-state area, with Huntington bordering Ohio and Kentucky.
4.97 out of 5 average rating, 102 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.
4.94 out of 5 average rating, 70 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.
4.93 out of 5 average rating, 187 reviewsPopular amenities for Chesapeake vacation rentals
Other great vacation rentals in Chesapeake

The Park House A 5 Bedroom Retreat w/Game Room &
5.0 out of 5 average rating, 34 reviews
A Westmoreland Gem
5.0 out of 5 average rating, 5 reviews
Luxury Cottage: Marshall, St. Mary’s, Downtown
4.95 out of 5 average rating, 59 reviews
Park Place Manor
4.8 out of 5 average rating, 74 reviews
Heart of Downtown Loft
4.88 out of 5 average rating, 33 reviews
Sleeps 7, Pet Friendly, Guest Favorite Comfy Home
4.97 out of 5 average rating, 58 reviews
Cozy Modern Getaway-Ritter Park! No Cleaning Fee!
4.92 out of 5 average rating, 92 reviews
WV Hobby Farm
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