Family-friendly vacation rentals in Highland County

5 out of 5 average rating, 19 reviews

Cottage in Hillsboro

Whitetail Quest Cottage, LLC

This cute little cottage is perfectly situated just 10 miles away from Hillsboro and only 4.7 miles from Rocky Fork State Park. Whether you’re here visiting family, chasing whitetail deer in the fall or calling spring gobblers or a fishing expedition. This is the ideal southern Ohio retreat in the heart of Highland County. The cottage offers a cozy stay with one queen and one twin bed. This is strictly a non-smoking home (outside only) It has a Smart TV with internet and is Pet Friendly with fee

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4.92 out of 5 average rating, 13 reviews

Guesthouse in Hillsboro

Rinal Rustic Resort 1B/1B guesthouse

10 min from the heart of Hillsboro, Ohio and a quick 3min drive to Rocky Fork Lake, this cozy barn-style guest house offers the perfect country escape. Tucked 500 feet from the main house, our 1B/1B blends rustic charm with modern comfort. Inside, you’ll find a living room with a large sectional couch, kitchen with a coffee maker, two-burner cooktop, mini fridge & sink. Bathroom is stocked with fresh towels, & bedding is cleaned prior to your arrival. Onsite pond for catch and release fishing.

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4.86 out of 5 average rating, 28 reviews

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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5 out of 5 average rating, 17 reviews

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.

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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, 123 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 .

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4.98 out of 5 average rating, 107 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. AC, WIFI, Smart tv. Sit on the porch to watch the sunset and deer graze! There is no washer/dryer.

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4.96 out of 5 average rating, 126 reviews

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.

Cabin in Hillsboro

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.

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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.

4.84 out of 5 average rating, 89 reviews

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).

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4.99 out of 5 average rating, 84 reviews

Cabin in Hillsboro

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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4.97 out of 5 average rating, 86 reviews

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.

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4.9 out of 5 average rating, 144 reviews

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.

Cabin in Hillsboro

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.

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