Family-friendly holiday rentals in Highland County

5 out of 5 average rating, 10 reviews

A hillside view captures the rustic pole barn style building surrounded by lush green trees. Sunlight filters through the leaves, creating a dappled effect on the well-maintained lawn leading up to the structure, which features large windows for natural light.

Cottage in Bainbridge

New Barndominium on an 8-acre property

Take it easy at this unique and tranquil getaway in the heart of Paint Creek Lake and Rocky Fork Lake areas. Amish built pole barn style building high up on a hill on an 8 acre property near the Highlands Nature Sanctuary Cedar Run Trail. Property has private wooded trails that back up to cliffs, a stream and a small waterfall. This is an outdoor experiences area and one of Ohio's Amish communities. There is a guide in Airbnb app that shows local places of interest and food/grocery options

Place to stay in Wilmington

An historic red brick schoolhouse is shown at dusk, accentuated by soft exterior lighting. A gravel parking area is visible in front, with wooden fencing surrounding the yard. The setting includes open fields in the background and a few trees, enhancing the rural ambiance.

4.89 out of 5 average rating, 113 reviews

Historical late 1800s Schoolhouse/Community Church

Explore Cowan Lake WEC and Amish stores and bakeries all within minutes from this historic Schoolhouse and picturesque setting. This 1882 Rural Schoolhouse is sitting on an acre of the original land. It includes a newly built 29 x 24 Hemlock sided closed pavilion with outside entities. Includes a park like charcoal grill, a gas grill , horseshoes court and corn hole boards. Great for outside gatherings and animal friendly inside and outside, including horse trailer parking and moving vans .

4.93 out of 5 average rating, 41 reviews

A charming white barn features a green roof and double doors, framed by vibrant autumn leaves. The sunlit area is surrounded by well-maintained lawns and mature trees, providing a serene view of the picturesque farm setting.

Farm stay in Hillsboro

Charming Farm-stay Get-Away by Rocky Fork Lake

An hour east of Cincinnati & southwest of Columbus Minutes from Rocky Fork Lake And a world away from everything. Come visit a farm in Amish country, where the grass is greener, your coffee is smoother and the stars shine brighter; a place where you can catch a few fish and your breath. Close to adventure, yet quietly tucked away on a 82-acre picturesque farm, The Carriage House is a quiet retreat from a noisy world - the perfect place to slow down, re-connect & create treasured memories.

A rustic cabin exterior is surrounded by lush greenery, featuring a blue-green facade with wooden shutters. The entryway includes a small set of wooden steps leading up to a covered porch. Decorative string lights are mounted above the porch area.

4.94 out of 5 average rating, 34 reviews

Boro Bunkhouse

Relax with the whole family at this peaceful place to stay. Secluded in the woods with 60 acres of trails to hike and play disc golf. The front porch looking over a one acre pond. Hot tub is 💯 maintained and the heavy metal in the local water will MAKE IT GREEN. If you complain about it you didn’t read this. Outdoor grilling. 3 miles from Rocky Fork Lake and Pike County Off road ATV park. Bring your four wheelers and enjoy our trails. Fish or grille out with the whole family as it sleep

A spacious living area features a high, wood-paneled ceiling and large windows allowing natural light. Comfortable seating is arranged around a central coffee table, with an inviting stone fireplace as a focal point. A television stands on a console, and a dining area is visible in the background.

4.96 out of 5 average rating, 115 reviews

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.

A rustic cabin features a green metal roof and natural wood siding, surrounded by lush greenery. A walkway leads to the entrance, with flower boxes on the windows and a mix of landscaping elements enhancing the inviting exterior.

4.99 out of 5 average rating, 76 reviews

Country Cabin

If you’re needing a quiet, peaceful getaway, you just found it! Country Cabin is cozy and home away from home, which sits on shared property with the owners. Just 10 minutes to town for all your essential needs. If you like hiking, fishing, and boating Rocky Fork State Park, and Paint Creek are within a half hour drive. Venture on into Adam’s county where you’ll find Serpent Mound and the Amish market. Check out my Guidebook for restaurants, fun things to do and more!

Superhost

A compact kitchen is featured, equipped with white cabinetry and a marble countertop. Cooking utensils hang above a double sink, with a microwave and stovetop integrated into the cabinetry. Natural light streams in through a window, bringing the outdoors inside. The entry door is visible on the right.

4.89 out of 5 average rating, 129 reviews

In the pines cabin

Make some memories at this unique and family-friendly place. Experience tiny house living in our little cabin. Enjoy beautiful Rocky Fork Lake, Amish countryside, hike and explore The Arc of Appalachia. Boat rental is just down the road at Bayside Bait and tackle. Our cabin has 2 full size beds upstairs in loft area as well as a comfy queen sofa that makes a decent bed also. There is a small table and chairs. There is also a larger refrigerator on covered back porch.

4.96 out of 5 average rating, 141 reviews

A living room is presented with gray walls and a large area rug featuring a floral pattern. A gray sofa is arranged with decorative pillows, complemented by a chair and side table. Soft lighting is provided by two lamps on wooden tables, enhancing the inviting atmosphere.

Guest suite in Hillsboro

Shipp Haus c. 1891, Upstairs Suite

Welcome to the historically charming Shipp Haus c.1891. Built, by Dr. Shipp, in 1891, Shipp Haus is registered on the National Register of Historic Places. The home features two Airbnb spaces , a main parlor, and an owner's suite. The main parlor operated as an antique shop for several decades, and is now home to Shipphaus Mercantile. Shop online for the perfect unique gift, original artwork, new travel bag, or some local Hillsboro made items.

4.98 out of 5 average rating, 65 reviews

The cabin's exterior showcases a rustic log facade and a metal roof. A welcoming porch is accompanied by two chairs and a stack of firewood. Soft evening light emanates from one window, hinting at the cozy interior, while surrounding trees shed their leaves in autumn.

Cabin in Leesburg

The Cabin at Friendly Acres

Our antique, fully restored cabin is a cozy place to rest in the country. It's great for star watching, bird watching, or gathering by the fire either inside or out. If you love outdoor adventures it would make a great base camp for your hiking, kayaking, or hunting trip. We've tried to make the cabin comfortable but we ask potential visitors to be mindful that it's still a bit rugged, just like the land around it. It's a real country hideaway.

4.94 out of 5 average rating, 32 reviews

The exterior of the modern home is depicted, featuring a spacious front porch supported by wooden beams. A landscaped area with small shrubs is located in front, while a clear sky with soft clouds enhances the setting. The driveway indicates easy access to the home.

Home in Hillsboro

503 N West

Welcome to our charming new 2BR/2BA home in the heart of Hillsboro! This beautifully designed space features an open floor plan, two queen beds, and a queen sofa sleeper for extra guests. Enjoy a short walk to The Porch restaurant and the new pickleball courts. Perfect for a relaxing getaway or a business trip this home offers modern comfort with small-town charm. Book now and experience the best of Hillsboro!

A rustic log cabin stands surrounded by autumn foliage, showcasing a wooden porch with railings. Natural wooden textures create a warm appearance, and a welcoming front door provides access to the retreat. The landscape is accented by fallen leaves, enhancing the cabin's natural setting.

4.98 out of 5 average rating, 46 reviews

Country Charm

Seeking a place to unwind Country Charm in Highland county Ohio says it all, This one bedroom / one bathroom retreat is located 10 minutes south of Hillsboro, just thirteen minutes from Rocky Fork State Park and less than thirty minutes from Paint Creek State Park. Adams County is just south of Highland and features Serpent Mound and numerous Nature preserves, Cedar Fall and Adams Lake State Park.

The cabin's exterior features a mix of reclaimed logs and modern materials, with a rustic stone chimney. A porch with seating options provides a welcoming entrance, surrounded by lush greenery and trees that enhance the secluded atmosphere.