Vacation rentals in Winchester

Top Shelf Loft on Main St.

Have a top shelf experience at our Airbnb on Main Street, dating back to 1861. This 2nd floor apartment offers modern amenities & views of downtown Augusta from the balcony, including its mural & the river. Ideal for up to 4 guests, it includes a king bed, a queen Murphy bed in the open living area, and a full bathroom. A short walk to the Beehive, Augusta Pub, Carota's Pizzeria, Tabletop Traditions & the General Store. 2.2 mi-Soli Tree wedding venue, 0.5 mi-Distillery, 1.2 mi-Baker Bird Winery

Modern log home in the Appalachian foothills

Get away from it all at this rural retreat loaded with modern amenities to ensure a comfortable stay. The log home is located on a quiet farm just a short distance from the Appalachian Highway in Southern Ohio. Take a walk on the property or relax on one of the porches. You might see deer, turkey and other wildlife. (Hunting is not allowed.) The house is just a short drive from Amish country, Serpent Mound and other family-friendly activities. Good for couples, solo adventurers and families.

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.

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

Relax and Connect at the River

This is the perfect couples getaway! Arrive with everything you need for a few days then take a deep breath. On exhale everything not directly related to the river is turned off. Then mix and match the following activities on repeat….river and critter watching, drinks/cuddling by the fire, hot tubing, snuggling, napping, snacking, streaming...occasionally throw in some fishing, kayaking, and open fire cooking on the cast iron cookware.

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.

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 Pet Friendly Farmhouse

Welcome to our charming 3-bedroom, 1-bathroom farmhouse, nestled in the fields just outside of Blanchester, Ohio. This entire house is a cozy retreat, perfect for a relaxing getaway with family or friends. With a picturesque setting, a fenced yard for your beloved pets, and stunning views of 25 acres of lush farmland, you'll experience the tranquility of rural living while still being conveniently close to nearby cities.