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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Guest favourite

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!

LocationFamilyAmenities

4.93 out of 5 average rating, 87 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.

FamilyValueCondition

4.86 out of 5 average rating, 51 reviews

Top Guest favourite

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

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.

LocationValueCondition

5.0 out of 5 average rating, 35 reviews

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

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.

LocationValueLayout

4.93 out of 5 average rating, 212 reviews

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

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.

LocationFamilyPool

4.99 out of 5 average rating, 68 reviews

Top Guest favourite

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.

ValueFamilyCheck-in

4.87 out of 5 average rating, 289 reviews

Top Guest favourite

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- We will have property around The Cabin being logged during September. This will be Mon-Fridays, approximately 7am-4pm only. Message us for more information/concerns. *Be sure to read house rules and other notes before booking.

ValueLocationAir conditioning

4.99 out of 5 average rating, 456 reviews

Top Guest favourite

A charming farmhouse is set against a clear blue sky, featuring a metal roof and a welcoming front porch adorned with white railings. Lush greenery and colorful flowers line the gently sloped pathway leading to the entrance, enhancing the serene rural landscape.

Home in West Union

Foothills Farmhouse - West Union, Ohio

Relax with the whole family at this private, peaceful newly renovated 1930s farm house. Camping and rustic themes abound in each room. Resting on 6 acres, the property is complete with an orchard, outdoor fire pit, and plenty of open space. The three spacious bedrooms sleep 8. Located just outside of West Union, you are close to the Ohio Brush Creek, Amish country and so much more! A quiet getaway with all of amenities available to make your vacation fun, relaxing and one to remember.

FamilyLocationTV

5.0 out of 5 average rating, 67 reviews

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

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

FamilyLocationAccess

4.99 out of 5 average rating, 113 reviews

Top Guest favourite

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).

LocationFamilyIndoor spaces

4.98 out of 5 average rating, 66 reviews

Guest favourite

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

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.

LocationValueNearby

4.97 out of 5 average rating, 140 reviews

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

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)

ValueFamilyComfort

4.98 out of 5 average rating, 103 reviews