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Vacation rentals in Winchester

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Winchester

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

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Guest favorite
The living area features a warm wood-paneled interior with vaulted ceilings. Two recliners and a cozy sofa are positioned around a wooden coffee table. Large windows allow natural light to fill the space, while decorative elements enhance the rustic feel.
Home in Piketon
4.93 out of 5 average rating, 364 reviews

Modern log home in the Appalachian foothills

Get away from it all at this rural retreat loaded with modern amenities to ensure a comfortable stay. The log home is located on a quiet farm just a short distance from the Appalachian Highway in Southern Ohio. Take a walk on the property or relax on one of the porches. You might see deer, turkey and other wildlife. (Hunting is not allowed.) The house is just a short drive from Amish country, Serpent Mound and other family-friendly activities. Good for couples, solo adventurers and families.

Guest favorite
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!

Top guest favorite
A cozy living area features a light-colored sofa adorned with decorative pillows. Two armchairs offer additional seating, while a round wooden coffee table sits atop a patterned area rug. A vibrant plant adds a touch of greenery, and natural light filters in through a window.
Apartment in Milford
4.94 out of 5 average rating, 530 reviews

One Bedroom Apt in Historic, Downtown Milford

Clean, comfortable, boutique-hotel feel. Newly updated, one-bedroom apartment on Main Street in historic Milford. 30 min drive to downtown Cincinnati. Apartment sits directly above Harvest Market, a specialty market with coffee bar, smoothie bar, prepared foods, snacks, craft beer, wine and more. Enjoy free coffee or espresso drinks during your stay. Walk to restaurants, brewery, shops, parks, the Little Miami River, or bike on the Little Miami Scenic Trail. Bike rentals across the street.

Top guest favorite
An open living space is enhanced by a modern design featuring a cozy seating area with leather and fabric furniture. A vintage area rug anchors the space, while an elegant chandelier hangs from a beautifully detailed tin ceiling. A flat-screen TV and fireplace are visible on the wall.
Apartment in Augusta
4.99 out of 5 average rating, 198 reviews

The Bank House on Main St.

Come experience this unique Airbnb. In 1861, the Bank House was home to Bracken County’s first bank. This 1st-floor apartment still features the original tin ceiling and exposed brick from the 1800s. It will comfortably sleep 4-5 with a queen bed, a twin-over-full bunk (in a semi-private area), and two baths. Steps away from the Beehive, Augusta Pub, Carotas Pizzeria, Tabletop Traditions & the General Store. 2.2 mi - Soli Tree venue. 0.5 mi - Augusta Distillery. 1.2 mi - Baker Bird Winery

Guest favorite
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 favorite
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 favorite
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 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
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 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
4.98 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 favorite
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 favorite
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 favorite
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.

Popular amenities for Winchester vacation rentals

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