Holiday rentals in Winchester

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Top-rated holiday rentals in Winchester

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Top guest favourite

The cabin, constructed of dark wood, is framed by lush greenery and colorful wildflowers. A slanted metal roof reflects natural light. A welcoming porch features a decorative wreath and potted plants, providing an inviting entrance to the secluded woodland retreat.

Cabin in Blue Creek

4.94 out of 5 average rating, 188 reviews

The Nut House at Trails End, unique forest retreat

The Nut House is nestled in the 65000 + acre Shawnee State Forest. It is a unique COMPLETE get away in the forest in Southern Ohio. With 16’ cathedral ceilings, custom crafted artisan interior that compliments the view! Blue Creek has earned the name “The Little Smokies” for good reason. Free WIFI, Outdoor grill area, fire pit, music, fireplace, Roku TV and games are provided. Close to historic West Union and the Ohio River town of Portsmouth Miles of hiking and biking to explore!

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

4.94 out of 5 average rating, 181 reviews

Solstice Haven A-Frame on Private 20 Acres

An A-Frame designed and built by architect Jose Garcia in a peaceful and private setting in Adams County, Ohio. Rest, relax, and recharge while walking the trails on our 20-acre wooded property or fill the heated outdoor cedar soaking tub with fresh water for a relaxing soak. Visit the nearby Serpent Mound, Amish country, or nature preserves. Wildflowers in the summer, cozy Nordic fireplaces during the winter, and star gazing on clear nights, Solstice Haven is the perfect year round retreat.

Guest favourite

The exterior of a quaint studio cabin is surrounded by vibrant fall foliage, featuring trees adorned in golden leaves. A welcoming porch is accessed by wooden steps, and a decorative wreath adorns the door. An umbrella provides shade over the porch area.

Guest house in West Union

4.93 out of 5 average rating, 46 reviews

Amish Country Studio - 1 Bed, 1 Bath - Fire Pit

This private studio on wooded property is in the heart of Adams County, OH Amish country. An Amish bakery is nearby and hiking trails abound! Enjoy the sunset, Amish buggies trotting by, the fire pit or explore local history museums. Scenic country roads make for beautiful morning & evening walks. To see local tourism ideas click, “Show More" under the Location. Need an extra bed and bath? Add on our Amish Country Cabin nearby on the same property. 1 hour from Cincinnati, OH.

Superhost

A compact kitchen is featured, equipped with white cabinetry and a marble countertop. Cooking utensils hang above a double sink, with a microwave and stovetop integrated into the cabinetry. Natural light streams in through a window, bringing the outdoors inside. The entry door is visible on the right.

Cabin in Hillsboro

4.89 out of 5 average rating, 127 reviews

In the pines cabin

Make some memories at this unique and family-friendly place. Experience tiny house living in our little cabin. Enjoy beautiful Rocky Fork Lake, Amish countryside, hike and explore The Arc of Appalachia. Boat rental is just down the road at Bayside Bait and tackle. Our cabin has 2 full size beds upstairs in loft area as well as a comfy queen sofa that makes a decent bed also. There is a small table and chairs. There is also a larger refrigerator on covered back porch.

Guest favourite

A living room is presented with gray walls and a large area rug featuring a floral pattern. A gray sofa is arranged with decorative pillows, complemented by a chair and side table. Soft lighting is provided by two lamps on wooden tables, enhancing the inviting atmosphere.

Guest suite in Hillsboro

4.96 out of 5 average rating, 139 reviews

Shipp Haus c.1891, Upstairs Suite

Welcome to the historically charming Shipp Haus c.1891. Built, by Dr. Shipp, in 1891, Shipp Haus is registered on the National Register of Historic Places. The home features two Airbnb spaces , a main parlor, and an owner's suite. The main parlor operated as an antique shop for several decades, and is now home to Shipphaus Mercantile. Shop online for the perfect unique gift, original artwork, new travel bag, or some local Hillsboro made items.

Top 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

4.98 out of 5 average rating, 126 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.

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

4.95 out of 5 average rating, 125 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.

Top guest favourite

The image features a charming cottage facing the Ohio River, with a tree-lined path leading along the water's edge. A decorative barrel and a statue of a horse add character to the front, while lush greenery surrounds the property, providing a peaceful atmosphere.

Townhouse in Augusta

4.99 out of 5 average rating, 269 reviews

☼ South Bank Station on the River w/Serene Views ☼

This Sweet Ohio River Getaway circa 1864, offers the charm and magic of bygone days, unmatched spectacular River Views, & rare privacy & quiet. Enjoy the best of all worlds with easy access to Main Street shops & restaurants as well as reliable fiber optic internet. Exclusively available for just one or two Guests, let the beauty & enchantment of Augusta & your graciously Southern Surroundings refresh & elevate your spirits!

Guest favourite

A four-person hot tub is set on a covered patio, offering views of the river through large openings. Surrounding the tub are several seating options, with a natural landscape of trees visible nearby. The tranquil water reflects the soft light, creating a serene atmosphere.

Tiny home in New Richmond

4.97 out of 5 average rating, 451 reviews

Stargazers' Retreat: A Tiny Home on the Riverside

Welcome to The Stargazers' Retreat at Visions on the River - A Tiny Home community on the Riverside. This newly built tiny home is #1 of 3 and set along the banks of the Ohio River, minutes away from the historic river town of New Richmond, Ohio and a 25-minute drive to Downtown Cincinnati and Northern Kentucky. This space is perfect for anyone looking to retreat and reconnect with nature. Take part in our adventure!

Top guest favourite

A tree-lined driveway leads to a gated entrance, flanked by stone pillars featuring eagle sculptures. Beyond the gates, glimpses of the guest house and lush greenery are visible, creating a serene atmosphere as it invites guests into the property.

Guest house in Cincinnati

4.91 out of 5 average rating, 298 reviews

The Cincinnati Hideaway

The Cincinnati Hideaway is located on approx. 11 acres, only minutes off Expressway 275. We are near Eastgate, Amelia, Batavia & only 25 minutes from downtown. Our place is best for business travelers, couples, & friends who would like to experience a relaxing stay in a country style setting right around the corner from Jungle Jim's, a movie theater, grocery stores, a park, mall & lots of restaurants.

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

4.95 out of 5 average rating, 20 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.

Guest favourite

The cabin's covered front porch features two wicker chairs and a small table, surrounded by greenery. Two green doors with arched windows serve as the entrance, and a pathway leads to the gravel parking area. Outdoor lighting accents the inviting space.

Guest house in Vanceburg

4.92 out of 5 average rating, 143 reviews

Boulder Brook Cabin

Wonderful cozy guest cabin in the woods. Knotty pine living space with outdoor elements throughout. Open concept with beds/living room/kitchen all sharing the same space. Full stocked kitchen with Kuerig coffee bar ready to start your day off right! Covered front porch for sitting and enjoying the views. Parking at front door.