
Vacation rentals in Winchester
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Top-rated vacation rentals in Winchester
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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.

Franklin House - quiet country getaway
Completely restored 150 year old farmhouse located in the middle of 112 rolling acres of farmland. Beautiful views every direction. Original hand hewn beams, gas fireplace, new kitchen and bath. Uniquely decorated. Fully stocked kitchen. Bedroom has king bed. Located on quiet county road about 6 miles from Hillsboro. Close to Rocky Fork Lake, Amish community, and Paint Creek Lake State Park. AC, WIFI, Smart tv. Sit on the porch to watch the sunset and deer graze! There is no washer/dryer.

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 Roundabout Cabin near Portsmouth, Ohio
Nestled on 4 wooded acres along Pond Creek, this one of a kind cabin will certainly be a unique experience. Walls of windows blur the lines between inside and out, connecting you with nature in every room. The house is very open, with rooms winding around the central stone fireplace with varying levels. The kitchen is stocked with supplies for preparing your own meals, but downtown Portsmouth restaurants are just 10 minutes away. Outside are patios for relaxing and woods for walking.

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.

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.

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.

Charming Pet Friendly Farmhouse
Welcome to our charming 3-bedroom, 1-bathroom farmhouse, nestled in the fields just outside of Blanchester, Ohio. This entire house is a cozy retreat, perfect for a relaxing getaway with family or friends. With a picturesque setting, a fenced yard for your beloved pets, and stunning views of 25 acres of lush farmland, you'll experience the tranquility of rural living while still being conveniently close to nearby cities.

Barndominium! Farm Setting. Private Porch. WIFI.
We would love to welcome you to our little piece of Heaven at The Farm Inn. We have created a cozy little home like atmosphere inside our newly built barn on our 80+ acre farm in Pike County, Ohio. We love the peaceful evenings by the fire soaking up the stars & enjoy the wildlife surprises. It's VERY common to see whitetail deer grazing in our hay fields. We do have WiFi!

Cozy, Amish-built cabin/amazing sunset view!
Amish-built cabin on 80 acres: fields, woods, and privacy. Upgraded linens, kitchen with island, cozy living room with pellet stove, private bath, and a large loft bedroom that overlooks the living room. Watch the sunset from your deck and enjoy the serenity of nature. If you are looking for peace and quiet away from the hustle and bustle...welcome home. (Pet friendly)
Popular amenities for Winchester vacation rentals
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Destinations to explore
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- Great American Ball Park
- Kings Island
- Cincinnati Zoo & Botanical Garden
- Cincinnati Music Hall
- Carter Caves State Resort Park
- Newport Aquarium
- East Fork State Park
- University of Cincinnati
- Duke Energy Convention Center
- Cincinnati Art Museum
- Heritage Bank Center
- Smale Riverfront Park
- Xavier University
- Paycor Stadium
- Hard Rock Casino Cincinnati
- TQL Stadium
- Contemporary Arts Center
- National Underground Railroad Freedom Center
- Eden Park
- Newport On The Levee
- Krohn Conservatory
- American Sign Museum
- Washington Park
- Findlay Market





