Holiday houses in Leesburg

The Ogden House (2 miles from WEC)

Welcome to our charming newly renovated home located in Wilmington, Ohio. This house was built by my husband's grandfather in 1954 and has been in our family ever since. This spacious interior is equipped with everything you need for an enjoyable and comfortable stay. We are located 2 miles from the World Equestrian Center, 3 miles from Lake Cowan, 2.3 miles from Majestic Springs Golf Course, 6.5 miles from Wilmington Air Park, and 7 miles from Robert's Center. This house has a new HVAC system.

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

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.

Private A-Frame on 20 Acres | Remote-Work Friendly

Guests consistently tell us the same thing: the photos don’t fully capture how peaceful it is here. Tucked among 20 private wooded acres in the rolling hills of southern Ohio, Solstice Haven is a modern A-frame retreat designed for quiet mornings, long walks through the woods, productive workdays, and evenings spent beneath the stars. Whether you’re planning a romantic getaway, a solo reset, or a week of remote work surrounded by nature, you’ll find the space to truly unplug or reconnect.

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.

Country Relaxation

Unwind and relax in this cozy little guest space, located in southern Ohio. The main area is a small kitchen/dining/living area combined. The kitchen has a fridge, 2 burner electric stove, coffee maker, teapot, and other essentials. 1 bedroom with queen bed and full bath. The entire space is for guests. There is a locked door and hallway between the apartment and the remainder of the house, where the owner lives. It is our goal to provide a clean and comfy place for you to stay!

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.

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.

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.

The Carriage House in the Heart of Uptown

The Carriage House in the Heart of Uptown Centerville!! Historic Charm with Modern Comfort. Built in 1897 and fully renovated in 2017, making it one of Centerville’s true hidden gems. Just steps from local restaurants, coffee shops and a scoop (or two) of Graeter’s Ice Cream. It’s perfectly located for your stay. Whether you’re planning a romantic weekend, visiting family, or simply looking to relax, this cozy retreat is the ideal place to unwind.

College Street Cottage

Charming cottage within walking distance of the Wilmington College campus and conveniently located near many local attractions and landmarks. Two bedroom, one bathroom with full kitchen, dining room, living room, rear deck, and private drive. Amenities include WiFi, Roku TV's in bedrooms and living room, full sized refrigerator, washer and dryer, coffee bar, and many other comforts of home.

Trail M Horse Farm GH#1, Wilmington, Ohio

Country lodging on a working horse farm, Trail M Farm. Spectacular view set on a hill surrounded by horses. Located 2 miles south of town. Also 4 miles from WEC (World Equestrian Center) and 8 miles from Robert's Center for those showing or attending any events. Pet friendly, 2 dog limit & well behaved in house. We ask that you crate your dogs if they are to be left unattended.