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Holiday houses in Winchester

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Winchester

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

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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, 192 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
A modern bedroom features a spacious bed with crisp linens against a textured stone wall. Large windows with shades allow natural light, while a small desk with a chair provides a work area. A minimalist light fixture and a flat-screen TV complete the inviting space.
Tiny home in Vanceburg
4.93 out of 5 average rating, 149 reviews

Riverview Getaway

This recently renovated historical building is located in the heart of downtown Vanceburg. Enjoy a beautiful view of the Ohio River across the street beside the Veteran’s Memorial Park while you take in the quaint small-town feel. Historical landmarks and dining options are within walking distance. Fun photo opportunity in front of the "Welcome to Vanceburg" mural located on the side of the Airbnb. Ample parking, & can provide a pack and play/high chair upon request. We can't wait to host you!

Guest favourite
Cabin in Peebles
4.95 out of 5 average rating, 187 reviews

Private A-Frame on 20 Acres | Remote-Work Friendly

Solstice Haven is a secluded A-frame cabin set on 20 private acres in Peebles, Ohio, designed for guests who want peace, privacy, and productivity. Whether you’re escaping the city, working remotely, or staying to recharge, this property has everything you need to feel refreshed. Surrounded by woods, private hiking trails, and a soaking tub, this cabin combines deep nature and modern comforts. High-speed WiFi makes it ideal for weekday stays, long weekends, and extended visits.

Top Guest favourite
Cabin in West Union
5 out of 5 average rating, 13 reviews

Amish Country Cabin - 1bed/1bath-Fire Pit-Kitchen

This private cabin 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 & bath? Add on our Amish Country Studio nearby on the same property: https://www.airbnb.com/l/YiFTH

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, 140 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
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
4.97 out of 5 average rating, 138 reviews

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.

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, 127 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, 132 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, 271 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!

Top Guest favourite
A stone house sits on a well-maintained lawn, surrounded by lush green trees. The two-story structure features a sloped roof and several windows, allowing natural light to enter. A small, landscaped area with flowers frames the entrance, enhancing the rural charm.
Home in Ripley
4.99 out of 5 average rating, 112 reviews

Stonehurst: 3 bedroom country home

Forget your worries in this spacious and serene country space! Historic, relaxed feel with modern conveniences. Situated in the beautiful Ohio River Valley with access to many interesting little towns nearby. Enjoy sightseeing, small town shopping and unique restaurant eating during the day then relax in the evening by the campfire in this charming country setting. Small family gatherings, bridal and baby showers are welcome.

Top 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, 22 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.
Guesthouse in Vanceburg
4.93 out of 5 average rating, 147 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.

Popular amenities for Winchester holiday rentals

  1. Airbnb
  2. United States
  3. Ohio
  4. Adams County
  5. Winchester