Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Guest favorite
Cottage in West Union

Lucky Hooks

Fishing and relaxation. Relax with the whole family at this peaceful place to stay. This cozy brand new home is on our 70 acre farm. Enjoy watching our cattle graze and beautiful views all around our pond! Yes, we are in the country but only a 10 minute drive to town. Close to Amish country, Serpent Mound, and Buzzard’s Roost! Space: We have plenty of room for you and your family! This is a spacious three bedroom home that includes a king size bed, queen size bed, and one twin size bunk bed!

4.93 out of 5 average rating, 87 reviews
Guest favorite
The living area features wooden flooring and a cozy seating arrangement with a brown couch and armchair. Natural light filters through multiple windows, highlighting decorative wall art and mounted deer antlers. A coffee table and side tables complement the space, offering a welcoming environment.
Home in West Union

Treasure at the end of the Road!

Forget your worries in this spacious and serene space. Enjoy hanging out on the covered porch reading a book or sharing stories with a beautiful view of a stocked pond (catch and release, bring your own poles).The deer are known to walk right past you. There is NO hunting. Enjoy the evening skies with a roaring fire on a star fillled night. Enjoy the bakeries and local Amish shopping, Serpent mound is a short drive away, plenty of hiking and kayaking to enjoy. Take a stroll through a local zoo.

4.93 out of 5 average rating, 30 reviews
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

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.

4.87 out of 5 average rating, 53 reviews
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

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.

4.93 out of 5 average rating, 213 reviews
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

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.

4.99 out of 5 average rating, 68 reviews
Top guest favorite
A modern wooden structure is reflected in a serene pond surrounded by lush greenery. Large windows and a distinctive roof design enhance the home’s unique architecture, nestled in a tranquil wooded setting.
Cabin in New Richmond

Nature Spa House | •Pool •Hot Tub •Sauna •Pvt Lake

Spa retreat steps from your own lake, set on 10 wooded acres with water views and total calm. Swim in the pool, soak in the hot tub, sweat in the sauna, or cast a line from the shore. End the day at the fire pit, then unwind in the game and movie rooms. Inside are thoughtfully furnished spaces and a well-equipped open kitchen for group meals. A resort-style stay for families and friends who want space, seclusion, and quality. Easy self check-in, ample parking; pets welcome with notice/fee.

4.87 out of 5 average rating, 290 reviews
Top guest favorite
The cabin's exterior features a mix of reclaimed logs and modern materials, with a rustic stone chimney. A porch with seating options provides a welcoming entrance, surrounded by lush greenery and trees that enhance the secluded atmosphere.
Cabin in Hillsboro

The Cabin Hillsboro, Ohio

Secluded, reclaimed log cabin. This hidden gem is a piece of the past with the comfort of modern amenities. Come sit a spell on either of the porch swings, enjoy a campfire by the pond, cozy up to the wood burning fireplace, or soak in the hot tub. *Please note- Property around The Cabin is being logged during September/October. This will be Monday-Friday, 8am-4pm only. Message us for more information/concerns. *Be sure to read house rules and other notes before booking.

4.99 out of 5 average rating, 459 reviews
Top guest favorite
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

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

4.99 out of 5 average rating, 115 reviews
Top guest favorite
The rustic cabin is illuminated warmly from within, presenting a welcoming sight against the twilight sky. A stone chimney stands alongside the porch, which features wooden beams and a rustic ambiance. The surrounding trees are silhouetted, enhancing the serene outdoor setting.
Cabin in West Union

"Clover" 1830s Cabin on Hills Fork Farm

This reclaimed 1830s cabin is a rural escape located on a working farm. You'll have access to the guest cabin, bath house, fire pit, grounds, and - upon request - our working blacksmith shop. Spend an afternoon meandering trails on 75 acres of farmland and forest, sip tea on the porch, or take a drive through charming Amish country. There are two cabins on the property, and both can be booked together if you wish (please see listing for "Timothy" cabin).

4.99 out of 5 average rating, 68 reviews
Guest favorite
An outdoor fire pit is surrounded by several wooden chairs, set on a lush green lawn. The lodge's exterior features multiple flags and is visible in the background against a vibrant sunset sky with soft purple and pink hues.
Home in Aberdeen

Minton Lodge - Relax, Rewind, Enjoy!

Privacy and peacefulness is what you'll experience at the beautiful Minton Lodge, a service offered by the Josh Minton Foundation. 4 bedroom and 2 full baths in a very remote location on a 49 acre wooded property . Wrap around porch, hot tub, fire pit, gas grill, smoker, and a wood stove in large living room. Walking trails with plenty of wildlife. Wifi, DirecTV, DVD player and two LCD TV's. 10 minutes from the Ohio River and Maysville, Kentucky.

4.96 out of 5 average rating, 146 reviews
Guest favorite
Home in West Union

Finding Grace

Escape to the peaceful charm of Amish Country with this cozy 1 BR 1BA studio. Perfect for a quiet retreat or a simple country lifestyle, this space blends rustic beauty with modern comfort. Surrounded by woods and wildlife. Close to Amish bakeries, scenic back roads, local hiking spots, Adams Lake and the Serpent Mound State Park. Ideal for anyone seeking tranquility and grace.

5.0 out of 5 average rating, 14 reviews
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

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)

4.98 out of 5 average rating, 103 reviews

Popular amenities for Winchester vacation rentals