Holiday rentals in Winchester Township

Highland Homestead

Escape to this cozy retreat nestled on a peaceful 1-acre lot surrounded by farms. This home features warm wood details throughout and a luxurious custom shower. Enjoy the tranquility of the countryside while staying just 10 minutes from essentials in Hillsboro. Adventures await! —Only 20 minutes to Rocky Fork State Park, Amish-country markets are within 20–30 minutes, and family fun at Long’s Retreat is just a 30-minute drive. Perfect for a quiet getaway with easy access to local attractions.

The Opal Cabin at Highland Hill

Take it easy at this charming A-frame cabin nestled in the foothills of Appalachia. Experience a relaxing and convenient stay on the edge of Waverly City limits. Our A-frame cabin is the perfect blend of rustic charm and modern comfort, providing you with an unforgettable getaway. As you step inside, you’ll be greeted by the warm and inviting ambiance of natural wood and large windows that bathe the interior in natural light. Relax in the hot tub & enjoy the scenic view from the balcony.

Franklin House - quiet country getaway

Completely restored 150 year old farmhouse located in the middle of 112 rolling acres of farmland. Beautiful views every direction. Original hand hewn beams, gas fireplace, new kitchen and bath. Uniquely decorated. Fully stocked kitchen. Bedroom has king bed. Located on quiet county road about 6 miles from Hillsboro. Close to Rocky Fork Lake, Amish community, and Paint Creek Lake State Park. AC, WIFI, Smart tv. Sit on the porch to watch the sunset and deer graze! There is no washer/dryer.

Jail Break Inn in Downtown Ripley

Welcome to Jail Break Inn, located in Ripley, Ohio! Experience history firsthand as you stay overnight in the converted old Ripley Jail. Immerse yourself in the authentic atmosphere with preserved architecture, iron bars, and brick walls. Our unique Airbnb offers modern comforts in converted jail cells. Explore Ripley's rich history, including the Ohio River, and the Underground Railroad. Book now for an unforgettable stay at Jail Break Inn, where the past meets comfort and intrigue!

Private A-Frame on 20 Acres | Remote-Work Friendly

Solstice Haven is a secluded A-frame cabin set on 20 private acres in Peebles, Ohio, designed for guests who want peace, privacy, and productivity. Whether you’re escaping the city, working remotely, or staying to recharge, this property has everything you need to feel refreshed. Surrounded by woods, private hiking trails, and a soaking tub, this cabin combines deep nature and modern comforts. High-speed WiFi makes it ideal for weekday stays, long weekends, and extended visits.

Stay a While | Warm & Cozy Bungalow

Step into a thoughtfully restored 1906 bungalow where historic charm meets modern comfort. Perfect for up to three guests, the space includes a comfortable queen bedroom and a queen sleeper sofa in the living area—ideal for couples, small groups, or solo travelers who want a little extra room. Located along historic Route 50, you’ll enjoy quick and convenient access to everything in Hillsboro, including local restaurants, shops, and everyday essentials—all just minutes away.

White Pine Cottage-cozy tiny home w/ earthy decor

Kick back and relax in this calm, stylish space.This 14x40 cottage is brand new with a front and back porch. The front porch is the whole length of the cabin with 4 rockers to sit in and relax. The back porch has seating that overlooks farmland and you may see an occasional deer grazing in the field. There is a gas grill on the back porch as well. We have a fenced private area with a fire pit and chairs to enjoy a fire on a cool night.

Lazy Spread Cabin

Forget your worries in this spacious and serene space. A long winding road will lead you to a quiet rustic secluded cabin nestled on wooded acreage in the country, where you can set aside the hustle and bustle of city life and just put your feet up and enjoy nature. Whether you want to explore natural trails, visit local Amish shops or just sit on the deck and do nothing or enjoy a soak in the Hot Tub - it is all here waiting for you.

Finding Grace

Escape to the peaceful charm of Amish Country with this cozy 1 BR 1BA studio. Perfect for a quiet retreat or a simple country lifestyle, this space blends rustic beauty with modern comfort. Surrounded by woods and wildlife. Close to Amish bakeries, scenic back roads, local hiking spots, Adams Lake and the Serpent Mound State Park. Ideal for anyone seeking tranquility and grace.

Charming Creekside Cabin with Dock

This lovely creekside cabin is on one of southwestern Ohio's premier deepwater fishing and boating streams. Private and cozy, this Amish-built retreat is well appointed and well cared for and has a large dock. The hosts are well known for their hospitality. The rate is a flat rate and there are no additional cleaning fees. This cabin is available only to singles and doubles.

Amish-built cabin on pond/amazing view!

Private, secluded cabin awaits. Enjoy 80 acres of fields, forests, and pond. Amish-built cabin with beautiful décor, full bath, loft bedroom, full kitchen with island. Watch the sunset off the back deck. Owner is easily accessible in case you need anything. If you are looking for peace and quiet with spectacular views...welcome home. (Pet friendly)

The Cabin Hillsboro, Ohio

Secluded, reclaimed log cabin. This hidden gem is a piece of the past with the comfort of modern amenities. Come sit a spell on either of the porch swings, enjoy a campfire by the pond, cozy up to the wood burning fireplace, or soak in the hot tub. *Be sure to read house rules and other notes before booking.