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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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Top 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 homes in Vanceburg
4.93 out of 5 average rating, 150 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
The front view of Limestone Bungalow showcases its blue siding and charming architectural details. The entrance features a covered porch with supporting columns and boxwoods on either side. A flag waves nearby, with soft light from the setting sun illuminating the surrounding area.
Home in Maysville
4.91 out of 5 average rating, 116 reviews

Limestone Bungalow 1920 Craftsman Row House

Limestone Bungalow is fully remodeled, pro decorated & all yours for your visit to historic Maysville. Downtown, walking distance to restaurants, shops. A beautiful 1182 sqft house. Downstairs is a living room, dining room, full kitchen w/vintage touches, 1/2 bath, washer/dryer. Upstairs you’ll find full bathroom, bedroom 1: king bed, bedroom 2: loft w/ futon twin sz, bedroom 3: full bed. Yard w/a deck, fire pit (March-Dec) and a watch markers shop, not restored. WiFi, 2 streaming tv’s HVAC.

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
5 out of 5 average rating, 55 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 favourite
An open living and dining area showcases an exposed brick wall contrasting with a modern kitchen. Tasteful furnishings include a leather sofa, two armchairs, and a wooden coffee table. A chandelier hangs from the ceiling, adding elegance to the space, while natural light enhances the inviting atmosphere.
Apartment in Augusta
5 out of 5 average rating, 202 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

Top guest favourite
A spacious building is viewed next to a calm pond, with reflections visible on the water's surface. Lush green grass surrounds the area, and trees accompany the backdrop, enhancing the serene outdoor setting. A deck is seen extending from the main building.
Cabin in West Union
4.98 out of 5 average rating, 62 reviews

Wesley's Ark Cabins Christian Camp

Wesley's Ark is a new & wonderful place that is desirable for those seeking a healthy Christian atmosphere. It has 19 acres of a beautiful country setting with woods. The camp has 3 Amish-built cabins that has 2 cabins that sleeps up to four people and 1 cabin that sleeps 2. We also have 6 frisbee disc baskets. Children 12 and under need adult supervision in the community center and the pond. Our cabins have bathrooms/showers. Community Center closed November to April. Please, no hunters!

Guest favourite
Cabin in Peebles
4.94 out of 5 average rating, 188 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.

Guest favourite
Guesthouse 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.

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, 141 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, 139 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.

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, 129 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, 138 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, 275 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!

Popular amenities for Winchester vacation rentals

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