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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Guest favorite
Cottage in West Union
4.93 out of 5 average rating, 87 reviews

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!

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
4.93 out of 5 average rating, 29 reviews

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.

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, 51 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.

Top guest favorite
A scenic pond is surrounded by lush green trees, reflecting the vibrant blue sky. Two docks extend into the water, offering access to the tranquil setting. A picnic shelter is visible in the background, enhancing the outdoor space.
Home in Sardinia
5.0 out of 5 average rating, 36 reviews

30 Acre Retreat: Pond, Hot Tub, Disc Golf & More!

Welcome to Alguire Acres! Take it easy at this tranquil getaway on nearly 30 acres. Enjoy the park like setting with manicured pond, 2 docks, shelter picnic area, disc golf, kayaks, hot tub and hobbit holes! The indoor space is pretty exceptional too! This spacious and light-filled home has two sections perfect for multiple families or friends. The Main House has 3 Bedrooms, 2 Bathrooms, a kitchen, and arcade space; the other section of the home has 2 Bedrooms, 1 Bathroom, and a kitchen too.

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, 212 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.

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
4.99 out of 5 average rating, 68 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.

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
4.99 out of 5 average rating, 457 reviews

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-We will have property around The Cabin being logged during September/early 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.

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
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 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
4.99 out of 5 average rating, 67 reviews

"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).

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.

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
4.92 out of 5 average rating, 72 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!

Guest favorite
Home in West Union
5.0 out of 5 average rating, 12 reviews

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.

Popular amenities for Winchester vacation rentals