Holiday rentals in Jackson

Elevated Wilderness | Mindful Retreat | 2 Kings

Executive Forest Sanctuary/2 King Beds, Hot Tub & Trails Escape to an architectural masterpiece set on 40 private, wooded acres. Designed for professionals, couples, and active adults seeking a high-end nature reset, Cabin Porch Paradise balances complete seclusion with proximity to Southern Indiana’s best destinations. Whether you are unwinding in the spa amenities, working remotely via high-speed fiber, or exploring the surrounding lakes and state parks, this is your ultimate ridgetop retreat.

Greenhouse Flat

The Greenhouse Flat This Zen hangout is part retreat, part cool-factor overload. You’ll find a space made for relaxing & unwinding. Features include: • Pool table for friendly competition • Kitchenette for snacks, drinks, and late-night cravings • Full bath with Jacuzzi tub • Custom steel shower with ipe wood floor • Deep soaking hot tub inside an actual greenhouse (yes, really) It’s calm. It’s cozy. It’s a little indulgent. Perfect for adults looking to unplug and soak it all in — literally.

Cheerful two bedroom Farmhouse with free parking

Your family will be located in a lovely Bloomington rural setting that is less than 10 miles from Indiana University and less than 5 miles from beautiful 10,750 acre Lake Monroe. You will be able to unwind on the front porch swing, relax on the spacious back deck or warm your hands and feet by the fire pit provided. If you are a foody you are within 10 to 15 minutes from the many Bloomington restaurants or if you prefer the cooking option there is a full kitchen for your culinary creativity.

2b/2b Home in Columbus

Located just minutes from downtown Columbus, this home is perfect for solo travelers and families alike. This historic home has been updated and has all the modern amenities that one would need, including a full kitchen with dishwasher, two full bathrooms, and washer & dryer. It is a short drive to Cummins, Columbus Regional Health, Dunn Stadium, The Commons, Mill Race Park, The Miller House & Garden, Zaharakos (a historic ice cream parlor with soda fountain), and Columbus Municipal Airport.

Treetop Adventure Seekers

From the drive up a 1 lane private road, to a spiral staircase to the treetop loft, this space offers seclusion & convenience with a side of adventure. A unique hillside tri-level, surrounded by 85 foot trees. Guest have full access to the main level & loft. Owner occupies the downstairs studio with private access. Enjoy a dreamy night's sleep in the loft’s queen bed or in the main level king bed. A bike’s ride away from the Park, Music Center, Hard Truth Hills & downtown Nashville.

Cozy Oaks-Dog-Friendly Barndo Retreat

Rustic-modern 3-bedroom, 2-bath barndominium on 4 acres, just minutes from Brown County State Park. Family and dog-friendly with a relaxing hot tub, cozy fire pit, and plenty of outdoor space to enjoy. Perfect for family getaways, multi-generational trips, or a peaceful retreat with friends and furry companions. We’re thrilled to welcome your pups to Cozy Oaks! We love hosting well-behaved dogs and want your whole family—four-legged members included—to feel right at home.

A Stone's Throw in Little Nashville, IN

Located in Brown County just over a mile north (or "A Stone's Throw") of the quaint Village of Nashville, IN. Your home away from home is in a quiet rural neighborhood where you are just minutes from shopping, restaurants, art galleries, music venues and all kinds of outdoor activities. The owner lives full time in the upper level with her service dog Jessie but you will probably never see her unless they are out in the yard playing fetch or working in the garden.

Red Cedar Log Cabin | Romantic + Hot Tub

Cozy, secluded, and full of charm, Red Cedar Log Cabin is the perfect Brown County getaway for couples. Soak in the private hot tub, unwind by the wood-burning fireplace, and enjoy the peaceful wooded setting. With rustic character, modern comforts, and easy access to Nashville, trails, shops, and local dining, this cabin is made for quiet mornings, cozy nights, and unforgettable weekend escapes. Book your stay and experience Brown County at its coziest.

Modern Nashville Home in the Woods

Welcome to Plāhaus — a modern retreat tucked into the woods of Brown County. #1 Most-wishlisted Airbnb in Indiana per Airbnb Designed for solitude, relaxation, and connection with nature, Plāhaus blends modern architecture with peaceful surroundings. Take in the views from the balcony, gather around the firepit, or explore nearby Nashville’s shops and restaurants. Perfect for romantic getaways, family escapes, or simply recharging from everyday life.

Cozy Home - You'll Love This Place + Garage

Conveniently located across from Lincoln Park Ball Diamonds & Hamilton Ice Center, and just blocks from Columbus Regional Hospital & Nexus Park. Close to restaurants and local activities. This comfortable, welcoming home is in a safe neighborhood and well-stocked with everything you might need. As a frequent traveler myself, I’ve done my best to think of all the essentials so you can relax and enjoy your stay.

Brown County Wonderland

Located between Columbus and Nashville Indiana, this airbnb includes all the fun things the outdoors has to offer. This entails a basketball court with two goals, pickle ball courts, hot tub, a stocked pond, hiking trails, and a private workout gym. 1 King Bed 2 Twin beds This airnbnb has its own entrance! It is NOT the entire house! If you stay longer then 4 days you may have access to the washer and dryer!

JET Away

JET Away to a beautiful brand new cabin in the country. The cabin is a wonderful escape for family, friends, or couples. We have WiFi, cable, and a fire pit. Enjoy the fall foliage in the months of October-November. This location is close to Brown County State Park which has horseback riding, zip line, & paintball. 10.8 miles away from Nashville with shopping & restaurants. Come enjoy a peaceful stay with us.