Holiday houses in Leesburg

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Top-rated holiday rentals in Leesburg

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A charming cottage features a welcoming front porch adorned with a wreath. Lush green grass surrounds the concrete pathway, leading to a small entrance. Large windows with black shutters provide ample natural light, and a fenced pasture is visible in the background.
Farm stay in Wilmington
4.96 out of 5 average rating, 251 reviews

Jesse Brooke Farm

Located 1/2 mile from the World Equestrian Center and 3 miles from Wilmington with easy access to shopping and restaurants. Situated on a small horse farm with beautiful pastures and lots of horses to look at. You will have complete privacy. Take a walk down the quiet road, or sit on the front porch and just enjoy. We are centrally located between Dayton, Cincinnati and Columbus. The cottage is completely remodeled with new kitchen & furniture. Come and enjoy the cozy comforts of home!

Guest favourite
An A-frame cabin is situated among trees, surrounded by vibrant autumn foliage. A gravel area leads to the cabin's entrance, featuring a dark exterior. A circular seating arrangement made of wood logs is visible, complemented by a stone perimeter decorated with gathered leaves.
Cabin in Waverly
4.98 out of 5 average rating, 231 reviews

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.

Top Guest favourite
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
4.98 out of 5 average rating, 103 reviews

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.

Top Guest favourite
A comfortable seating area features a gray sofa adorned with a yellow pillow. Two patterned windows are draped with sheer curtains, allowing natural light to brighten the space. A small television sits on a white cabinet, complemented by decorative artwork and a rustic chair.
Guest suite in Wilmington
4.93 out of 5 average rating, 206 reviews

The Honey Bee Airbnb! Lovely 1-bed in Wilmington

Enjoy a hometown experience at this centrally-located 1-bedroom guest house space! This guest suite has its own private entrance, with a small outdoor space for your enjoyment. Within walking distance to the Kava Haus (local coffee shop), the Wilmington Historic Museum, Lutheran Church (across street), and more! This suite is also a convenient 10-minute drive to the Robert’s World Equestrian Center, downtown dining is also a short 5 block walk or 2-minute drive, and so so so much more.

Guest favourite
The exterior of the house is presented with a welcoming porch area featuring a wooden roof and two white rocking chairs. A well-maintained landscape includes river stones and colorful shrubs, along with tall trees in the background, enhancing the natural surroundings.
Home in Chillicothe
4.95 out of 5 average rating, 358 reviews

Terrace Farmhouse - Chillicothe, OH

Are you in need of rest and relaxation? Want to kick back after a day of exploring the wonderful things our city has to offer. Conveniently located within 10 minutes from downtown Chillicothe, Ohio and only minutes away from Adena, Kenworth, VA Medical Center, Great Seal State Park, and Hopewell Culture National Historic Park. And only 36 miles away from Old Man’s Cave in the Hocking Hills. This home has a security camera located in the breezeway for property security only. #51863

Top Guest favourite
A single-story house with a light brown exterior and dark shingle roof is visible. The front features a covered porch with seating and manicured landscaping. A gravel driveway leads to an attached double garage, with an open space on the lawn and cornfields in the background.
Apartment in Leesburg
4.93 out of 5 average rating, 164 reviews

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!

Guest favourite
The exterior of the A-Frame showcases a modern design with sharp angles and a striking black facade. Large glass windows reflect the natural surroundings, while a landscaped yard features gravel pathways, small rocks, and plantings, creating a serene entrance to the retreat.
Cabin in Peebles
4.93 out of 5 average rating, 200 reviews

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.

Top Guest favourite
A gravel driveway leads to a welcoming cabin surrounded by trees, with a metal roof and a scenic backdrop of rolling hills. A wooden fence with decorative signs marks the entrance, hinting at the natural beauty that awaits.
Cabin in Peebles
4.99 out of 5 average rating, 113 reviews

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

Top Guest favourite
A spacious living room features warm hardwood flooring and ample recessed lighting. A large sectional sofa sits on a decorative rug, facing a flat-screen TV. Windows allow natural light to illuminate the space, with a bar area and a few stools in the background.
Apartment in Oregonia
4.99 out of 5 average rating, 145 reviews

Green Acres Farm-Apartment

Reconnect with nature at this unforgettable escape on a farm in the heart of Warren County. Private 900 sq. ft. two bedroom, 1 bath, living room and kitchenette looking out over 18 acres of privacy. Minutes to Caesar’s Creek Lake and hiking trails, the Renaissance Festival, Little Miami River canoeing and bike trails, Kings Island and World Equestrian Center. Right in between Cincinnati and Columbus minutes off of I-71.

Guest favourite
Tiny home in Minford
4.95 out of 5 average rating, 274 reviews

Creekside Haven Tiny Home

Welcome to Creekside Haven! Tucked along a peaceful creek in Minford, OH, our cozy tiny home is the perfect getaway for couples, families, or traveling professionals looking for comfort and convenience. Relax by the fire pit, play a game of corn hole, swing in the hammock, or unwind inside with all the comforts of home! Pets are welcome with prior approval. Please note we can only allow small dogs (under 30 pounds).

Guest favourite
A dining area features a round wooden table surrounded by four wooden chairs. A centerpiece with succulents is placed on a burlap runner. A ceiling fan with three lights hangs above, while a wall clock and decorative letters add character to the space.
Home in Waverly
4.95 out of 5 average rating, 180 reviews

The Farm Retreat at Pike

This country getaway retreat is just what you are looking for. We have designed our space with our guest’s privacy and relaxation in mind. Private gated access where memories are made that last a lifetime! Our most recent addition is a "Grain Bin Gazebo". This cozy backyard retreat is equipped with a gas grill, blackstone griddle, table and chairs. Backyard also has a brick patio, hot tub, hammock and fire pit.

Top Guest favourite
A blue guest house is shown, featuring a covered porch with wooden seating. The surrounding lawn is well-maintained, showcasing green grass and neatly trimmed bushes. Mature trees provide shade in the background, contributing to the peaceful setting of the property.
Farm stay in Wilmington
4.98 out of 5 average rating, 232 reviews

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.

Popular amenities for Leesburg holiday rentals

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  4. Highland County
  5. Leesburg