Vacation rentals in Cheshire

"Little Brick House" in the Heart of Rio Grande,OH

Welcome to our Little Brick House! Built in 1947, this home has a lot of the same charm and characteristics that you would see in a classic Farmhouse. We paid homage to its original design by renovating it to an updated Modern Farmhouse style along with a brand new kitchen and bathrooms. Located in the Heart of Rio Grande, you are within minutes of the original Bob Evans Farm, University of Rio Grande, Rio Ridge, and the Merry Family Winery. This house is rented under McAllister Properties LLC.

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!

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.

The Hunting Lodge @ Circle T Ranch

** Attention Hunters: Rates shown are not hunting rates: Please inquire for late-season (January) hunting rates. Thank you** ________ For over five years The Lodge has attracted travelers in need of rest, due to our close proximity off St. Rt. 7 and the US 35 corridor ( if eastbound use Rio Grande/St. Rt. 335 S exit - if westbound use Gallipolis/St. Rt. 7 S exit) and has hosted multiple employment bookings - for the complete solitude required for rest. ( Description cont. below ⬇️)

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.

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!

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.

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.)

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.

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.

Crystals Retreat - Hot Tub and Movie Room

This three-bedroom, three-bathroom house is perfect for families, friends, couples, or business travelers. Enjoy a private hot tub, movie room, and fully equipped kitchen. Close to attractions, dining, and shops, yet peaceful and relaxing. Clean, comfortable, and spacious—everything you need for a great stay!