
Holiday rentals in Cheshire
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Top-rated holiday rentals in Cheshire
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Ever After Hocking Hills
Ever After is a luxury two person A-Frame. Real Cedar shakes on both ends of the cabin with a modern interior. Oak hardwood floors throughout the main living space with breakfast nook seating. Large 55in Smart TV, Starlink WIFI, and streaming only. Choose between a jacuzzi bathtub or the beautiful luxury nero marquina tile shower. Fall asleep in the queen size Ever After loft with dual lit bedside tables. The hot tub gazebo over 20 foot above the ground is sure to make your experience memorable!

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.

The Hitch Caboose
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!

Castaway Cares
Nestled on a quiet hilltop you will enjoy 360° privacy in this rustic cabin that's spacious and unique! On the main floor you will find the fully equipped kitchen, living room with DVD player and retro game system, dining space, full bathroom & 2 bedrooms each with a queen & twin size bed. Downstairs you will find another living room, master bedroom with en suite bath, and second bedroom with a twin size bed. It can be the perfect space for families, friends groups, hunters and more!

Yellow Dog Barndominium
Our brand new barndominium is a 10 minute drive from Ohio University, yet sits on a 100+ acres in the country. You will find it located near the front of the property, feet away from a 16 acre private water ski lake with beautiful sunset views. Visitors can enjoy hiking, fishing and swimming during their stay. We designed this as a couples retreat, including a 4 person hot tub, but a second bedroom with a full bed and twin trundle can accommodate friends or family who may join you.

Ohio River Cottage
This is an Ohio River front private cottage on 7 acres . This cottage has a bedroom, living room, bathroom with shower, large screened deck and a separate outer deck. There is also a grill on deck. This is a great place to escape from stress and just relax! This cottage has WiFi and a 55 inch flat screen satellite TV. Enjoy the river views and watch the wild life . Easy accessibility to the local shopping , Hospitals and Restaurants 10-15 minutes. Pet friendly with a small fee

Creekside 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!

River Siren: Suite 1 (River view balcony)
A unique, freshly restored historical building in the quaint town of Pomeroy, Ohio. Feel like you're staying in an artsy NYC loft in the heart of Appalachia! Featuring stunning views of the Ohio River and Main Street from a spacious balcony. Located in a great central location just a short walk to restaurants, bars, coffee shops, boutiques, churches and more. (Suite 1 of 2 apartments located up a two-story walk up in historical building. Not handicap accessible.)
Popular amenities for Cheshire holiday rentals
Other great holiday rentals in Cheshire

Grandpa's Loft

Hillside A-Frame | Secluded | Hocking Hills

3 Bedroom/2 bath Hilltop Home

Parkview Suite

The Ridge Roost

Palmer Place, Lower Level

Farm Cabin with a View

Morris' Garage! Apt with WiFi!
Destinations to explore
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- Hocking Hills State Park
- Lake Logan State Park
- Ohio University
- Strouds Run State Park
- Hocking Hills Winery
- Lake Hope State Park
- Mothman Museum
- Burr Oak State Park
- Ash Cave
- Cantwell Cliffs
- Rock House
- Hocking Hills Canopy Tours
- Conkles Hollow State Nature Preserve
- Tar Hollow State Park
- Ritter Park
- Pleasant Hill Vineyards
- Capitol Market





