Vacation rentals in Chilo

The Cottage at Brianza Winery

Peaceful, country setting at Brianza Gardens and Winery. Lovely ranch 2 BR/1 B has all the comforts of home incl. W/D. Enjoy the scenic views and walking trails among the gardens and vineyards. Large GR/DR, eat/n/kit. The "Cottage" is adjacent to the "Bungalow", also listed on this site. The Bungalow is a 1BR, full kitchen apartment. If you need more space please book both properties. Sorry, no pets allowed or parties. Maximum occupancy is six people. $20 fee per person/per day over four people

The Bank House on Main - Walk Everywhere!

Come experience this unique Airbnb. In 1861, the Bank House was home to Bracken County’s first bank. This first 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

Buffalo Springs Distilling Company

It’s recently been brought to our attention about Airbnb scams! Please reserve with us or someone else that has a history! The Bourbon Trail The Buffalo Springs Distilling Company got it's start in 1868. It closed and it's warehouses were emptied out by the 1970's. This building is one of the last structures left on the site. This historic building was the main office and gatehouse for visitors to the distillery, so we can offer one Queen sized bedroom due to the size of the structure.

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!

Black Tie Affair - Eloquent Riverfront Experience

Welcome to A Black Tie Affair at Visions on the River - A Tiny Home community on the Riverside. This newly built home is #3 of 3 and set along the banks of the Ohio River, minutes away from the historic river town of New Richmond, OH and a 25-min drive to Downtown Cincy and Northern KY. This romantic space is perfect for anyone looking to retreat and reconnect with nature. With over 700 Five-Star happy guest reviews we are confident you will love it here! Take part in our adventure!

The Cottage at Asbury Meadow

Peaceful, relaxing private cottage that accommodates 4. (formerly the summer kitchen to the estate) Private bedroom with King Bed, living area offers single daybed and pullout trundle bed. Sitting on a quiet 10 acres next to the main house. No loud motorcycles or late night music. Short 12 min. drive to Augusta. For additional $16./person serving breakfast in main house, advance notice required when booking. Guests can shop in the "Silver Rabbit" gift shop for unique items.

KY’s #1 Wishlisted Stay-Treehouse and outdoor tubs

Escape to Kentucky’s 2026 most wishlisted Airbnb! A romantic treetop getaway with two outdoor tubs, twinkle lights, and a peaceful setting made for reconnecting. The treehouse features a large glass rolling garage door allowing stunning views of the sunset. The highlight is undoubtedly the double tubs overlooking the creek. ✔ Queen Bed ✔ Outdoor Deck with Seating ✔ Double Outdoor Bathtubs ✔ Outdoor Shower ✔ Composting Toilet ✔ Creek Access ✔ Indoor Cooking Station ✔ Hot Water

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.

☼ 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.

The York House at Catawba Farm

NEW RENOVATIONS FOR 2024! New Huge Primary Bedroom with En Suite!! Total of 2.5 bathrooms! Catawba farm is located at the actual site of the former town of Catawba. The town of Catawba in the late 1800’s had a blacksmith shop, general store, school, church, train station and pop. ~110. You will feel the history as you explore the 99 acre farm taking in the beautiful scenery or relaxing at the beautifully renovated farmhouse.

Quaint Cafe Loft with small town charm

Enjoy small town charm in a cozy, newly remodeled apartment that sits over top of a farm to table cafe. We've given thoughts to all the comforts of home, from the freshly roasted coffee (ask to see our roaster), to the fresh plants (take some cuttings home!) and comfortable outdoor cafe patio upstairs. Come downstairs for fresh baked cinnamon rolls or coffee or create yourself a dish in the fully equipped kitchen.