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 favorite
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, 59 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 favorite
An open living area features a gas fireplace framed by a rustic brick wall, with comfortable seating arranged around a wooden coffee table. Natural light illuminates the space, showcasing original hand-hewn beams on the ceiling and thoughtfully placed decorative pieces.
Farm stay in Hillsboro
4.98 out of 5 average rating, 101 reviews

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.

Top guest favorite
A spacious living area showcases a combination of original exposed brick and modern finishes. Light-colored hardwood flooring extends beneath a comfortable sofa and armchairs. A round dining table is set beside a wall-mounted television, while large windows are draped with soft curtains.
Apartment in Augusta
4.99 out of 5 average rating, 212 reviews

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

Guest favorite
Cabin in McDermott
4.86 out of 5 average rating, 505 reviews

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.

Guest favorite
Cabin in Peebles
4.93 out of 5 average rating, 196 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 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
4.96 out of 5 average rating, 141 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 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
4.97 out of 5 average rating, 134 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 spacious living area features rustic log walls, large windows allowing natural light, and wooden flooring. A cozy sectional sofa is positioned near a fireplace, while a dining area with a table and chairs is also present. Soft blue curtains complement the warm wood tones.
Cabin in West Union
4.95 out of 5 average rating, 146 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
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, 117 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 favorite
A single-story farmhouse is surrounded by vibrant autumn trees, showcasing shades of red and orange. A wooden deck is adorned with a green umbrella, while decorative pumpkins and potted plants are arranged at the entrance. A partly cloudy sky offers a serene backdrop.
Ranch in Blanchester
4.99 out of 5 average rating, 150 reviews

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.

Top guest favorite
The newly constructed barn-style property is viewed from above, surrounded by expansive green fields and dense forest. Gray gravel is present in the driveway area, with equipment housed under an overhang on one side of the structure.
Farm stay in Piketon
5 out of 5 average rating, 113 reviews

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!

Top guest favorite
A rustic cabin with a wooden exterior showcases a metal roof and a spacious front porch. The porch is bordered by vertical wooden railings and offers seating. Surrounding trees provide natural shade, enhancing the cabin's connection to its tranquil outdoor setting.
Cabin in Seaman
5 out of 5 average rating, 61 reviews

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

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