Holiday rentals in Chilo

Top Shelf Loft on Main St.

Have a top shelf experience at our Airbnb on Main Street, dating back to 1861. This 2nd floor apartment offers modern amenities & views of downtown Augusta from the balcony, including its mural & the river. Ideal for up to 4 guests, it includes a king bed, a queen Murphy bed in the open living area, and a full bathroom. A short walk to the Beehive, Augusta Pub, Carota's Pizzeria, Tabletop Traditions & the General Store. 2.2 mi-Soli Tree wedding venue, 0.5 mi-Distillery, 1.2 mi-Baker Bird Winery

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.

The Cabin at 114 Main Street with Hot Tub

Experience Augusta, KY in this charming 1800s log cabin just a block from the Ohio River! Walk to local pubs, shops, and wineries—plus a stop on the B-Line Bourbon Trail. Sleeps upstairs; not ideal for young kids or mobility concerns due to open stairs. Expect live music and occasional train noise. Pet- and motorcycle-friendly with hot tub and fire pit included (not refundable).

Hilltop Retreat at Wendt’s Wildlife Adventure

Take it easy at this unique and tranquil getaway. Newly remodeled home on a 125 acre farm that is home to Kentucky’s newest wildlife park & Daniel Boone’s last home in Kentucky. Expansive views, and a visit to Wendt’s Wildlife Adventure (open seasonally), which is owned & operated by your hosts, are sure to give you just the right amount of rest & adventure that you are seeking.