Holiday houses in Winchester

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Top-rated holiday rentals in Winchester

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

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A cozy cabin made of log sits under a cloudy sky. A front porch with wooden railing and chairs invites relaxation. The cabin features multiple triangular windows and a metal roof, surrounded by a grassy area and trees in the background.
Cabin in West Union
4.86 out of 5 average rating, 49 reviews

Griffis Game Hunting and Getaway

Enjoy a relaxing and clean getaway at our cozy cabin located in West union, ohio. It is a beautiful cozy place to getaway and enjoy family and friends on 90 acres of beautiful woods. Located near a county road and easy access to food, Amish, and more! Bow Hunting only, available at an additional cost. Deer are thick. Contact host for specific details and pricing about hunting. Fish in our small pond right down the road, ride your atv, grill out, enjoy the fire pit or a nice walk in the woods.

Guest favourite
Home in Georgetown
5 out of 5 average rating, 28 reviews

Southern Ohio Retreat w/ Private Hot Tub

White Oak Cottage is a charming rental set on the banks of White Oak Creek in southern Ohio. You'll find it nestled in the countryside between Georgetown and Mt. Orab, and about ten minutes from State Route 32. The cottage is equipped with the basics and a few extras to make your stay an enjoyable one. The bathroom and bedroom are thoughtfully furnished and the bedroom has a queen-sized bed. Outdoors there's a lovely deck that houses a completely private hot tub with a view of the creek.

Top Guest favourite
A spacious living room features a large red sectional sofa and a comfortable light blue recliner. A 65" TV is mounted on the wall, and large windows allow natural light to fill the area. A coffee table sits in front, adorned with decorative items and plants.
Home in Winchester
5 out of 5 average rating, 66 reviews

Welcome to Dancing Deer Acres!

Bring the family to this country haven. Enjoy 1500 sq. ft. of indoor comfort located near Amish communities and shops. New deck, summertime pool, fire pit, stocked pond and deer feeding station on 7 acres. Semi-detached house has private entrances. Host is available as needed but gives guests their privacy. Major stores are within 25 minutes. Hiking, fishing, hunting, fall festivals, Serpent Mound and beautiful views within an hour! On a paved road within 5 minutes of two major highways.

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, 207 reviews

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.

Guest favourite
Home in Hillsboro
4.97 out of 5 average rating, 88 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.

Top Guest favourite
A rustic cabin, featuring a welcoming wooden facade and a green metal roof, is surrounded by lush greenery. A wrap-around deck offers seating and decorative plants, enhancing the connection to nature. A gravel pathway leads to the cabin, providing a sense of tranquility.
Cabin in West Union
4.96 out of 5 average rating, 159 reviews

Lazy Spread Cabin

Forget your worries in this spacious and serene space. A long winding road will lead you to a quiet rustic secluded cabin nestled on wooded acreage in the country, where you can set aside the hustle and bustle of city life and just put your feet up and enjoy nature. Whether you want to explore natural trails, visit local Amish shops or just sit on the deck and do nothing or enjoy a soak in the Hot Tub - it is all here waiting for you.

Guest favourite
Home in West Union
5 out of 5 average rating, 8 reviews

Serenity Now

Escape to this serene home in the heart of Adams County, OH Amish Community. This peaceful home is surrounded by 2.5 acres of lush wooded land and an abundance of wildlife. Perfect for couples, families or solo travelers seeking a charming retreat. Sit by the fire-pit and listen to the Amish buggies trotting by, shop at local Amish businesses, spend the day hiking or visiting local state parks and lakes.

Top Guest favourite
A wooden dock extends over calm water, flanked by two light-colored adirondack chairs. Lush greenery surrounds the water, with trees lining the distant bank under a clear blue sky dotted with wispy clouds.
Cabin in Ripley
4.95 out of 5 average rating, 282 reviews

Charming Creekside Cabin with Dock

This lovely creekside cabin is on one of southwestern Ohio's premier deepwater fishing and boating streams. Private and cozy, this Amish-built retreat is well appointed and well cared for and has a large dock. The hosts are well known for their hospitality. The rate is a flat rate and there are no additional cleaning fees. This cabin is available only to singles and doubles.

Guest favourite
The interior features warm wood paneling with a decorative star accent on the wall. A dining area is provided with a wooden table and chairs, positioned under a light fixture. A doorway leads into a separate sleeping area, enhancing the cozy ambiance.
Cabin in Peebles
4.97 out of 5 average rating, 58 reviews

Country Cabin (Pine Valley Cabins)

We offer 720sq ft. of space for the whole family. 1 or 2 bedrooms with extra cots, walk in closets, stand up shower, washer/dryer, fridge, microwave, full stove/oven, coffee pot, cooking pots, dish-ware, a/c / heat in each room. Eat in kitchen with Amish made dinette set. Couch that folds out to make bed. Outside smoke-less fire pit with grill option. No pets Unless approved

Top Guest favourite
A secluded wooden cabin features a welcoming porch and is surrounded by lush greenery. Adirondack chairs are arranged around a fire pit, providing a cozy outdoor gathering space. The structure's sloped roof and natural wood finish complement the tranquil setting.
Cabin in Seaman
4.98 out of 5 average rating, 102 reviews

Amish-built cabin on pond/amazing view!

Private, secluded cabin awaits. Enjoy 80 acres of fields, forests, and pond. Amish-built cabin with beautiful décor, full bath, loft bedroom, full kitchen with island. Watch the sunset off the back deck. Owner is easily accessible in case you need anything. If you are looking for peace and quiet with spectacular views...welcome home. (Pet friendly)

Top Guest favourite
The exterior of a charming single-story home is set against a peaceful landscape. A spacious front lawn is bordered by blossoming trees, while the house features a metal roof and inviting porch. The surroundings suggest a tranquil rural setting, perfect for relaxation.
Home in Sardinia
4.97 out of 5 average rating, 33 reviews

Bradford Paradise

Welcome to Bradford Paradise. This charming 3-bedroom, 2-bathroom home in Sardinia, OH. Ideal for families, business travelers, or a small groups of friends, this fully furnished home offers a comfortable and relaxing stay. With a spacious layout and modern amenities, it’s designed to make your visit as relaxing and enjoyable as possible.

Top Guest favourite
Home in Ripley
4.99 out of 5 average rating, 121 reviews

Stonehurst: 3 bedroom country home

Forget your worries in this spacious and serene historic home! Historic relaxed feel with modern conveniences. Situated in the beautiful Ohio Valley with many interesting little towns nearby. Enjoy sightseeing by day and sitting by cozy campfire by evening in this charming country setting. We would love to host you!

Popular amenities for Winchester holiday rentals