Vacation rentals 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.

The Bank House on Main - Walkable Everywhere!

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

The Buckingham House

This beautiful, spacious *BRAND NEW* home is everything you need for a comfortable stay in Maysville! It has an open kitchen/living area as you walk in the door. The kitchen leads out to a back patio looking over a beautiful grassy area that is perfect for relaxing in the evenings. On the other side of the home is the beautiful master suite, a guest bed/bath and an office(can be converted into bedroom). Located 10 mins from downtown Maysville, 1 hr from Cincinnati & 1 hr from Lexington.

Jail Break Inn in Downtown Ripley

Welcome to Jail Break Inn, located in Ripley, Ohio! Experience history firsthand as you stay overnight in the converted old Ripley Jail. Immerse yourself in the authentic atmosphere with preserved architecture, iron bars, and brick walls. Our unique Airbnb offers modern comforts in converted jail cells. Explore Ripley's rich history, including the Ohio River, and the Underground Railroad. Book now for an unforgettable stay at Jail Break Inn, where the past meets comfort and intrigue!

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.

The Ville-Cabin

Nestled in the hills in the Ohio River Valley this 3 bedroom 2 bath cabin has the feel of being in the Smokey’s The Whipple Loop state hiking trail is right across the street and has a beautiful view while sitting on the front porch We have a 1940’s caboose that is being transformed into a guest hang out to read a book or play a game of cards and a fire ring and old corncrib shelter for a night time gathering Come and stay to relax - refuel and refresh !!

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.

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.

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.

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.

Grant Cottage, historic & charming Ohio River home

Experience a slice of Americana in this 200 year-old historic river front cottage. Unwind on the cozy front porch, enjoy the sound of the water from the dock (seasonal) and relax in comfort in the charming cottage full of character and modern amenities. The house is perfect for gathering groups of families and friends to experience the history of the town or play on the river, surrounding creeks and the countryside.

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. *Be sure to read house rules and other notes before booking.