Family-friendly vacation rentals in Highland County

4.88 out of 5 average rating, 33 reviews

Home in Hillsboro

Pool | Hot Tub | Massage | Theater | Game Room

Country Cornerstone Retreat - 4,700+ sq ft on 6 beautiful acres! ☞ Game room w/ pool table, air hockey, foosball & arcade ☞ Sauna & theater room ☞ 1:00 PM EST check-in ☞ 2 high-end Osaki 4D massage chairs ☞ Gym w/ red light therapy ☞ Private heated pool (seasonal - opens 5/21; closes 10/1) ☞ Hot tub ★ "Great to watch a sunset while relaxing in the hot tub!" ☞ Grill + picnic tables ☞ 10–60 min drive to Hillsboro, Mount Orab, Wilmington, Milford, Eastgate, Cincinnati ❤️Add us to your wishlist!

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4.98 out of 5 average rating, 112 reviews

An open living area features a gas fireplace framed by a rustic brick wall, with comfortable seating arranged around a wooden coffee table. Natural light illuminates the space, showcasing original hand-hewn beams on the ceiling and thoughtfully placed decorative pieces.

Farm stay in Hillsboro

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 & ARC. WIFI, Smart tv. Sit on the porch to watch the sunset and deer graze! There is no washer/dryer.

Indoor spacesKitchenAccuracy

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, 131 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 .

KitchenFamilyComfort

4.94 out of 5 average rating, 51 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

Amish Country Retreat: Farm Animals & Family Fun

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.

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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.

4.99 out of 5 average rating, 457 reviews

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. *Please note-We will have property around The Cabin being logged during September/early October. This will be Monday-Friday, 8am-4pm only. Message us for more information/concerns. *Be sure to read house rules and other notes before booking.

FamilyIndoor spacesBreakfast

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.

4.96 out of 5 average rating, 47 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

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4.85 out of 5 average rating, 94 reviews

A cottage with a spacious deck, accessible by steps, is framed by a lush green lawn. Outdoor furniture, including an umbrella-shaded table, is visible on the deck, providing a welcoming space for relaxation. Tall trees surround the structure, enhancing the serene environment.

Home in Hillsboro

Cozy 3 Bedroom Cottage, Direct Lake Access & Dock

***This property is currently undergoing an interior remodel, will be completed no later than April 30th*** Reconnect with loved ones in this family-friendly cottage on the lake. We are located directly on the lake & offer a privately owned dock for your use. You will find kayaks, lifejackets, and other lake toys waiting for you to enjoy. Our cottage offers two bedrooms and 1 bath on the main floor and a 3rd Bedroom and Bath in the basement (accessible through outside entrance only).

FamilyKitchenParks

4.99 out of 5 average rating, 88 reviews

Country Cabin

If you’re looking for 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 Millers Amish market. Check out my Guidebook for restaurants, fun things to do and more!

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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, 137 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. While this is a true disconnect and place of relaxation- we do have neighbors nearby. 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 or parties allowed.

FamilyIndoor spacesWalkability

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, 154 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.

FamilyIndoor spacesBathroom

4.96 out of 5 average rating, 148 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

Historic Downtown Suite | Walk to Everything

Stay in the heart of downtown Hillsboro in a private 2nd-floor suite inside historic Shipp Haus, built in 1891. Walk to local restaurants, shops, and the town square, then come home to a comfortable queen bedroom, living room, mini kitchen, full bath, and sunny sitting room. Listed on the National Register of Historic Places, Shipp Haus combines historic character with a comfortable, private stay in the heart of town.

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