Holiday rentals in Winchester

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!

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

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.

Dani's Darling Den

Enjoy a cozy stay in a mid century boho retreat!. Located in Pleasant Ridge, this is a one bedroom efficiency apartment with a full bathroom (shower, no tub), wet bar, mini fridge, and microwave, toaster/oven/air fryer. One queen bed and an additional guest can sleep on the fold out couch. The space has a private entrance and free parking on a quiet street. Pet friendly and and fenced yard. Three minute walk to the park, 7 minute walk to the local entertainment district.

In the pines cabin

Make some memories at this unique and family-friendly place. Experience tiny house living in our little cabin. Enjoy beautiful Rocky Fork Lake, Amish countryside, hike and explore The Arc of Appalachia. Boat rental is just down the road at Bayside Bait and tackle. Our cabin has 2 full size beds upstairs in loft area as well as a comfy queen sofa that makes a decent bed also. There is a small table and chairs. There is also a larger refrigerator on covered back porch.

Adorable & Chic 2BR/2BA with Coffee Bar

This unique home has a style all its own, with ultra clean lines and a nordic flair. This charming house will delight up to four guests and boasts a fully stocked kitchen and 2 full baths. Everyone will leave feeling special. There are two queen size beds with luxurious finishes. The full coffee bar includes a Keurig, a drip coffee maker, coffee grinder, french press and also pour over equipment. This recent renovation has all new appliances and furniture.

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.

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.

☼ 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!

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.