Vacation rentals in Cheshire

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Top-rated vacation rentals in Cheshire

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Top guest favorite
A single-story home with a covered porch features a star decoration on the exterior wall. Flower pots with vibrant blooms are placed at the entrance, and a gravel driveway leads to the property, bordered by lush greenery and tall trees.
Home in Crown City
4.97 out of 5 average rating, 226 reviews

Hunters Deeradise

Our Deeradise includes 60 acres of private hunting ground. Our 60 acres (private hunting) also borders a 30 acre tract of public hunting ground. Also there are 11,000 acres of state owned public hunting ground within 5 miles. Perfect for hunters. Twisted Vine Winery within 5 miles. We have a convenient store a few minutes away together with a dine in restaurant within five miles. Quiet neighborhood. Perfect for a couple's getaway. Leave the city behind and enjoy our country lifestyle.

Top guest favorite
A simple loft above a detached garage is featured, showcasing a wooden staircase leading to the entrance. Large windows are present, allowing natural light to illuminate the exterior. The setting includes a landscaped area with a stone path, enhancing the accessibility of the entrance.
Guesthouse in Gallipolis
5 out of 5 average rating, 55 reviews

Grandpa's Loft

Simple loft above a detached garage. Includes a king-size bed, cable TV, mini-fridge, microwave, pod, or ground coffee maker. Minutes to the Root athletic center, Skyline Lanes, Gallipolis, Point Pleasant and the Mothman Museum and Festival, the University of Rio Grande, and Bob Evan's Farms. About an Hour to Jackson, Charleston, Huntington, and Athens. The property is not handicap accessible. The property is designed for two adults but a full-size air mattress is available for kids.

Top guest favorite
A serene vineyard landscape is captured with lush green grapevines in the foreground and a quaint white cottage nestled among rolling hills in the background. Soft clouds are visible in the sky, adding to the tranquil ambiance of the scene.
Cottage in McArthur
5 out of 5 average rating, 117 reviews

Winery Cottage - Chevalier Vineyards Hocking Hills

Stay right in the vineyards of a small, farm-to-table, family run winery! The Winery Cottage is a quaint two bedroom cottage tucked far enough away from the winery for complete privacy yet close enough to walk just a few minutes past the vines to enjoy a glass of wine in our winery tasting room. The cottage is nestled alongside a private natural spring pond, and has its own entrance and driveway. Enjoy all the panoramic vineyard views and tranquility that this unique property has to offer.

Guest favorite
A newly built house is set on a gravel driveway, surrounded by lush greenery. The exterior features a gray facade with wooden accents. A spacious porch is visible at the front, furnished with seating and offering a welcoming entrance.
Home in Pomeroy
4.95 out of 5 average rating, 103 reviews

Hillside Haven - 3BR, 2BA, w/ Hot Tub!

Welcome to Hillside Haven. A 3 BR, 2 BA Home with Hot Tub. This home is newly built in 2024. Hillside Haven is nestled into the hillside of a 20 acre property off a paved road in SE Ohio. This property is surrounded by wildlife in a serene outdoor setting. Watch the stars, lounge on the porch, or relax in the hot tub. You can also take a hike around the property or gather around by the fire pit. This is the perfect place to keep your worries away. Come stay with us and see for yourself.

Top guest favorite
A modern cabin features a distinctive dark exterior with a sloped roof. Large windows allow natural light to enter, framed by wooden accents. A spacious wrap-around deck is visible, bordered by a wooden railing, with colorful autumn foliage in the background.
Cabin in Gallipolis
5 out of 5 average rating, 81 reviews

Wilderness Luxury Cabin

Peace and quite awaits you at Farver Acres. These new cabins feature wrap around decks, large gas grill, outdoor gas fire pit on deck and deck furniture. On the inside you'll find radiant floor heating, individual room controlled air conditioning, a full kitchen featuring hickory cabinets, granite countertops including a dishwasher. You will also find two king size beds in private bedrooms, a sleeper loveseat, full size bathroom and a full size washer and dryer! No pets allowed.

Top guest favorite
Cabin in Point Pleasant
4.97 out of 5 average rating, 213 reviews

Frazier’s Cabin

Peaceful & beautiful views. Less than 2 miles from downtown. Your own private walking path. Escape from stress to this cozy cabin on 3.1 acres. A country setting with fruit trees and wild berries. Wake up to deer just outside your door. Visit downtown Pt. Pleasant where you’ll find multiple shops, restaurants and the Mothman Statue. There’s also Tu Endie Wei State Park and a river walk with hand painted murals along the flood wall. A PERFECT place for a Mothman enthusiast!!

Top guest favorite
A classic bedroom features a four-poster bed topped with a deep red quilt. Two bedside lamps flank the bed, and a small chair is positioned beside a dresser. Light filters through the sheer curtains, illuminating the ornate area rug on the wooden floor.
Home in Point Pleasant
4.96 out of 5 average rating, 142 reviews

629 on Main Rental B Upstairs

Take it easy at this unique and tranquil getaway. This 100 year old 4 square home was previously home to dentist office to a local dentist for many years. Located in the historical district of Main Street;this property is within 2 blocks of the world’s only Mothman museum. Shops, restaurants, river museum, flood wall murals displaying the history of Point Pleasant and the riverfront and Tui-endi-Wei parks are also some of the attractions within walking distance of the property.

Top guest favorite
Home in Patriot
4.99 out of 5 average rating, 136 reviews

Runaway Retreat - No Cleaning Fee

NO cleaning fee! 👫 I'll REIMBURSE for Kids under 12, just message! 🐾WELL BEHAVED dogs stay free! Enjoy the tranqulity of this space...just runaway for a bit! Come get some R&R for a weekend or a while. Perfect for couples, families/friends, hunters, traveling workers, etc. Enjoy a relaxing space where you can just breathe! Expect a clean & cozy spot you'll never want to leave. We're close enough to town to quickly grab groceries or shop, but quietly nestled in the country!

Top guest favorite
A charming A-frame cabin is featured, surrounded by gently sloping hills. Its wooden exterior is complemented by large front windows and a welcoming green door. A spacious deck is visible, furnished with chairs, offering a serene view of the natural landscape.
Cabin in Albany
4.97 out of 5 average rating, 233 reviews

Camp Forever Cabin West

Escape to the rolling hills of Southeastern Ohio at Camp Forever! Our property is located in the countryside, perfect for a peaceful getaway. We offer amenities such as a hot tub, fire pit and lots of games! Camp Forever has a primary bedroom and lofted beds upstairs. Please note that there is another cabin 67 ft apart. Camp Forever is 20 minutes from Ohio University, and a Short 5 minute drive to 2 Wineries! We love pets and insist you bring them along for your stay.

Top guest favorite
A spacious cabin resides among hemlock trees, featuring a two-story design with large windows that invite natural light. An outdoor deck with seating is visible, offering views of the lush surroundings. The entry is framed by wooden railings and a gentle path leads to the door.
Cabin in New Plymouth
4.99 out of 5 average rating, 262 reviews

Hocking Hills & Hunting Hideaway

Forget your worries in this spacious and serene space. Come enjoy this cabin centrally located on 90 acres, sitting back on a beautiful stocked pond! Updated in 2021, this is a beautiful place to come and enjoy nature, with all the amenities. You can have breakfast on an upstairs balcony while watching ducks and wild game around the pond. The unique feeling of being tucked away in the hemlock trees just really sets the mood at this unique cabin.

Top guest favorite
A wooden deck overlooks the serene Ohio River, featuring a round table with two folding chairs and an additional chair. The railing frames the water view, while sunlight brightens the space, highlighting the natural wood grain of the flooring.
Cabin in Gallipolis
4.95 out of 5 average rating, 263 reviews

Large Scenic Cabin with Amazing View

Nestled in the trees high above the water, the Overlook Cabin offers a peaceful, comfortable, and intimate experience of the Ohio River, with a large riverfront window, 8x12ft deck, & jacuzzi bath. The 12x40ft space has a queen, 2 twins, another bed in the loft, and a couch, and would be great for families, hunters, or couples. Local coffee provided. Owners live onsite should any issues arise. Pet friendly. Free wi-fi available.

Top guest favorite
A wooden deck wraps around a cabin, featuring a hot tub and a dining area with four chairs. Large windows and a covered entryway provide views of the surrounding trees, enhancing the connection to nature. The entrance is flanked by hanging planters.
Home in Pomeroy
4.97 out of 5 average rating, 286 reviews

Sweet Peace Forest

Sweet Peace Forest is a secluded nature retreat located in Southeast Ohio. It is 30 minutes from Athens and 20 minutes from Pomeroy. It exudes warmth and nature from the 30 acre forest where it sits, to the ponds, to the carefully crafted and recently remodeled home. No matter which way you look, there's something pleasing to the eye and soothing to the soul.

Popular amenities for Cheshire vacation rentals