Holiday rentals in Cheshire

The Hitch Caboose with hot tub

Nestled in the middle of a 900-acre private farm in Fraziers Bottom, this Caboose turned Tiny Home offers an awesome getaway for guests. We’ve completely renovated both inside and out with a massive deck including a hot tub, fire-pit and outdoor furniture with a view to die for! A cozy sleeping area, ft. a queen bed, and a relaxing living room with a sofa bed across from a unique bay window dining area! We’ve got a private bathroom with a shower, this space is perfect for a soothing getaway!

Peak Retreat is a private 3 bedroom house.

Relax with the whole family at this peaceful place to stay. The bedrooms feature a king bed with half bath ensuite, a queen and a full bed. Excellent sunset views from the front porch. There are abundant opportunities to see wildlife especially whitetail deer. A fire pit and seating is available with all the necessary supplies to make a fire. Whole home generator. Come enjoy this newly renovated peaceful retreat in the country The private property is a short 5 minute drive to Pomeroy Ohio .

Palmer Place - 2nd Floor

Situated just blocks from the beautiful Ohio River, this relaxing retreat offers the perfect Appalachian getaway. The clean, inviting interior welcomes you home after a day spent perusing the charming shops in nearby Pomeroy and Gallipolis. Enjoy a cup of coffee and fresh pastry at River Roasters, take a stroll along the riverfront, buy a unique gift for a loved one (or yourself), and finish the day with great food at Court Street Grill. PalmerPlace - your small town home away from home.

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.

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.

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.

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!!

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.

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.

The Raven

Welcome to The Raven, a 550 square foot cozy 1-bedroom wooded retreat near Athens, Ohio. Enjoy a queen bed, walk-in closet, full bath, washer/dryer, and a full kitchen with bar seating. Relax in the living room with a pull-out sofa, TV, Wi-Fi, games, and more. Dine outside on the patio bistro set. Just off the highway, close to shops, eateries, wineries, and a speakeasy. 20 mins to Athens and Ohio University, 30 to Pomeroy, 40 to Hocking Hills—your peaceful escape awaits!

Rocksprings Retreat•Private Pool•15 Miles from OU

Welcome to Rocksprings, a spacious, gated home nestled at the edge of the woods just 15 minutes outside Athens, Ohio. Located on the grounds of Rocksprings Wellness (formerly Fur Peace Ranch), this property carries a rich creative history and has been thoughtfully reimagined as a peaceful retreat. Situated on 42 acres with walking trails and surrounded by nature, Rocksprings is a place to slow down, rest, and reconnect. Pool opens May 28, 2026.

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.