Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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

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Superhost
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, 50 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.

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

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Top guest favorite
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, 67 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.

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Guest favorite
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, 208 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.

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Guest favorite
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
4.96 out of 5 average rating, 131 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.

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Guest favorite
The living area features a brown leather sofa on a textured rug, complemented by a standing lamp and a small side table. A dining table with high-backed chairs is positioned nearby, while natural light flows in through large windows adorned with sheer curtains.
Cabin in Winchester Township
4.97 out of 5 average rating, 140 reviews

White Pine Cottage-cozy tiny home w/ earthy decor

Kick back and relax in this calm, stylish space.This 14x40 cottage is brand new with a front and back porch. The front porch is the whole length of the cabin with 4 rockers to sit in and relax. The back porch has seating that overlooks farmland and you may see an occasional deer grazing in the field. There is a gas grill on the back porch as well. We have a fenced private area with a fire pit and chairs to enjoy a fire on a cool night.

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Top guest favorite
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, 162 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.

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Guest favorite
The entrance features a white door framed by a brick facade. A light fixture is mounted beside the door, with a neatly landscaped area of greenery and stones surrounding the entryway.
Apartment in Mount Orab
4.91 out of 5 average rating, 68 reviews

Charming Townhome

Welcome to our charming 2-bedroom, 1-bath townhome nestled in a serene country setting. Our home offers a fully equipped kitchen with all the essentials to make you feel right at home. Whether you're cooking a family meal or enjoying a quiet breakfast, you'll find everything you need. Conveniently located next door is a laundry facility. Book your stay today and experience the perfect blend of comfort and convenient!

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Top guest favorite
Home in West Union
5 out of 5 average rating, 10 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.

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Guest favorite
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

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Top guest favorite
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)

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Top guest favorite
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.

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Popular amenities for Winchester vacation rentals