Holiday houses in Underwood

Patio Home Charlestown State Park & River Ridge

Welcome to your 5 star super host home away from home! This spacious patio home sleeps 7 guests & includes free parking for 2 vehicles, 2 full baths & a fully equipped kitchen. Located in a quiet, relaxing neighborhood just 20 min from the Louis Muhammad Ali Int’l Airport, min from Charlestown State Park & River Ridge Commerce Center. Perfect for professionals & contractors. It’s the perfect place to relax while enjoying the comfort & privacy of your own home with fast Wi-Fi & cozy furnishings.

The Log Cabin at StoneLedge

Please note the Log Cabin is a private home BUT the entire cabin is not avaliable for use when booking 4 guest or less. Nestled on an expansive 80 acre horse farm the log cabin is the perfect escape. Hike the 30+ acres of woods that boast a creek and waterfall. Relax on the cozy front porch while enjoying the sounds of nature. The Log Cabin is 10 minutes off of I71 exit 22. Less than 3 minutes to Ashbourne Farm & approximately 10 minutes to Hermitage Farm. ***PLEASE READ THE ENTIRE LISTING

Comfort de Casa

Our cozy home, set in a quiet neighborhood with safe streets for walking/running, is just a 15-minute drive from Louisville. With a full kitchen, dining room, and spacious living room, this three-bedroom home is great for families or couples to stay comfortably! The full house is available for guest use, except for a few locked closets. Enjoy the new four-seasons room and deck!! House rules: —No more than three vehicles —No parking on street! —Quiet hours: 10 pm-8 am —No parties/ extra guests

Anjuna House - a Scandi riverfront forest getaway

Welcome to the enchanting retreat of "Anjuna," nestled among a sprawling forest in the heart of southern Indiana. This modern 4-bedroom, 3 bathroom luxury cabin features 14' floor-to-ceiling windows, and 1000+ sqft deck! Outside there are 12 acres of forest to explore, an outdoor shower and a tranquil river which meanders through the property. Anjuna is near Knobstone trail, Marengo Cave, and the bourbon trail in Louisville. Bring family, friends or just yourself to relax or explore at Anjuna!

Canton Cottage- Modern Farmhouse 2 Bedroom

The Canton Cottage Built in 1901, this freshly remodeled two bedroom home is the perfect place to lay your head down after a long day. Located only 4 minutes from wal-mart and the rest of amenities that Salem has to offer. This home features new appliances, a workspace, two full beds, one queen bed, a sectional couch, and a quiet country setting to relax in. We have ordered new windows and are waiting on them to be installed. In the mean time 2 of our windows are cracked but sealed off.

Atoka Farms

If you are looking to get away in seclusion and be with Mother Nature, this is the home. Very quiet, with a running creek beside the home. Walking distance to the Ohio river, two outdoor decks, one with a grill. A car port, full kitchen, two full baths, paved driveway, trees all around. The home sits between two hill ridges surrounded by 180 acres. It is a park like setting. 30 minutes from Gene Snyder and I-71 (Louisville). Historic Lagrange Ky and Madison In, are a must see and close by.

Close to Louisville~Hot Tub~Fire Pit~Game Room

Welcome to Stone Creek, a private 3 acre estate conveniently located minutes to Louisville, KY. This is the Ultimate Getaway! Upon entering the premises, you will find a custom iron security gate requiring coded access. Stone Creek boasts 2500+ sq ft of luxury living space complete with a full kitchen, laundry, and office. Guests will have full use of the grounds including the hot tub, fire pit, and the numerous covered decks & patios. Perfect romantic getaway or multi person retreat.

Enchanting Lakeside Cabin in 50 Acres of Gardens!

Escape to the Lakeside Cabin at Hollyhock Gardens, a secluded retreat where cozy cabin charm meets lake views. Nestled on 50 private acres, this lakeside cabin is ideal for romantic getaways, family vacations, or relaxing nature retreats. Enjoy wooded walking trails, open fields, and two covered porches overlooking the land. Inside, unwind with a hot soaking tub, in-unit laundry, and a fully equipped space. Just 21 miles from downtown Louisville, it’s a serene escape with easy access.

The Cottage by the Woods

This small but newly renovated Cottage by the Woods offers a peaceful country alternative to an airbnb stay. The cottage is lightly decorated for seasonal transitions. It is located 15 minutes from downtown Madison, IN. A partial wrap around deck allows for a tranquil cup of coffee while bird watching. Free WiFi and Roku TV is provided along with other small amenities including various flavored coffee's for your morning cup of joe and a waffle making station.

Charming Tiny House In Scottsburg

Welcome to your perfect little getaway in the heart of Scottsburg! This cozy, tiny house offers comfort, style, and convenience—just two blocks from the historic town square with local shops, cafés, and restaurants. Step outside and enjoy your own patio, or take a short walk to the square and explore all that downtown Scottsburg has to offer. Perfect for solo travelers, couples, or anyone looking to experience small-town charm from a cozy home base.

My Old Kentucky Dome

An elevated camping “glamping” experience. This brand-new one of a kind geodesic dome is located on a private road that leads you to an overlook featuring one of the most beautiful countryside views in Kentucky. While this getaway experience is nestled deep in the woods, it is also a close drive to all the conveniences you can imagine. This is an off the grid outdoor experience with a ½ mile gravel road including a steep hill. AWD or 4WD advised.

Riverfront Cottage

Wake up to peaceful Ohio River views at this charming 2-bed, 1 bath waterfront cottage, where mornings start with coffee on the screened porch and evenings end watching the sunset over the water. With private dock access, cozy indoor spaces, and a quiet setting just 25 minutes from downtown Louisville, this home is perfect for couples, small families, or anyone looking to unplug and relax by the river.