Vacation rentals in Winchester

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.

Welcome to Dancing Deer Acres!

Bring the family to this country haven. Enjoy 1500 sq. ft. of indoor comfort located near Amish communities and shops. New deck, summertime pool, fire pit, stocked pond and deer feeding station on 7 acres. Semi-detached house has private entrances. Host is available as needed but gives guests their privacy. Major stores are within 25 minutes. Hiking, fishing, hunting, fall festivals, Serpent Mound and beautiful views within an hour! On a paved road within 5 minutes of two major highways.

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.

The Rocky Moose Cabin by Rocky Fork Lake

Come enjoy a getaway at this peaceful, unique cabin with convenient, easy access to Rocky Fork lake- just down the road from the boat ramp. Hiking trails, fishing, boating and playgrounds all within a few minutes drive. This is a true disconnect and place of relaxation. Enjoy the quiet, serene atmosphere of the cabin both inside and out. 10 minutes from Amish stores and bakery and 10 miles from downtown Hillsboro. Unwind at the end of your day in the hot tub. No pets allowed.

Black Tie Affair - Eloquent Riverfront Experience

Welcome to A Black Tie Affair at Visions on the River - A Tiny Home community on the Riverside. This newly built home is #3 of 3 and set along the banks of the Ohio River, minutes away from the historic river town of New Richmond, OH and a 25-min drive to Downtown Cincy and Northern KY. This romantic space is perfect for anyone looking to retreat and reconnect with nature. With over 650 Five-Star happy guest reviews we are confident you will love it here! Take part in our adventure!

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.

Indian Crossing Cabin

Relax with the whole family at this peaceful place to stay has over 50 acres to explore over 2000 ft of Ohio brush creek frontage to enjoy relaxing , fishing , kayaking and many more recreational fun things less than 5 minutes away from Amish shops to find bake goods and furniture and much more ,enjoy some hunting on the farm during hunting season lots of wildlife , only 15 miles from Serpent Mound , we have a golf cart for you to enjoy many trails here to ride it on

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.

Stonehurst: 3 bedroom country home

Forget your worries in this spacious and serene country space! Historic, relaxed feel with modern conveniences. Situated in the beautiful Ohio River Valley with access to many interesting little towns nearby. Enjoy sightseeing, small town shopping and unique restaurant eating during the day then relax in the evening by the campfire in this charming country setting. Small family gatherings, bridal and baby showers are welcome.

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.

Bradford Paradise

Welcome to Bradford Paradise. This charming 3-bedroom, 2-bathroom home in Sardinia, OH. Ideal for families, business travelers, or a small groups of friends, this fully furnished home offers a comfortable and relaxing stay. With a spacious layout and modern amenities, it’s designed to make your visit as relaxing and enjoyable as possible.

Bear Necessities

Honey & Wi-Fi. The Bear Necessities! Relax on the front porch or enjoy the warmth of the fire pit on a chilly evening. Located approximately 1 mile outside the village of West Union, this country setting offers the Bear Necessities you need to place the hustle and bustle of work on hold for a few nights.