Smoking-friendly holiday rentals in Southern Indiana

Artistic 3 Bed Apartment 4 Creatives

Welcome to this smoking space in Indianapolis designed 4 creatives. This space is minutes from downtown and located above CityDump Records (A Hip-Hop Recording Studio). Enjoy the art, outside fire pit/grill, full kitchen, jetted tub, 3 Beds, and Tv's in every room. This listing IS NOT for light sleepers. Music can be heard from studios below. Miles to: 3 - TCU Amphitheater 2 - Lucas Oil / Convention center. 2.3 - Gainbridge Fieldhouse 4 - Indy 500 6 - Airport Blocks from IndyGo bus route 24

Walk To Maker’s Mark | Wagon Wheel Barndominium

🏆 Voted one of the Top “5 Unique Stays in Marion County, Kentucky” – January 30, 2026. Welcome to the Wagon Wheel Barndominium, a private barndominium just steps from Maker’s Mark on the Bourbon Trail. If you’re looking to relax and kick back at a remote place on the Bourbon Trail with friends you’ve found your space! This unique rustic Barndominium on 8 acres along Hardins Creek sleeps 6 comfortably. Relax with multiple outdoor seating areas to enjoy creek views, Makers cropland, and wildlife.

Huge cabin near Mammoth Cave Nolin Lake Sleeps 16

Hillybilly Hill-ton! HUGE cabin at Nolin Lake. Sleeps up to 16 people. 5 porches, western saloon, large hot tub, firepit, arcade area, luxurious decor & amenities. Huge kitchen w/ frig, ice machine, stove, dishwasher, microwave, coffee bar, gas grill & blackstone. 2 outdoor showers. 2 washer & dryers. 6 flat screen TV's, games & more. 5 min to Nolin Lake Wax area & 20 min to Mammoth Cave. RV connection & plenty of room to park lake toys. Perfect place for family reunions & retreats.

Mod Lodge Family & Pet Friendly EV Charger Hot Tub

This is an Apartment /Mother in law suite that is connected to my home. You have a separate Front and Back door. One bedroom, Full kitchen, queen bed, and queen sofa bed in the livingroom. Driveway Parking. Backyard and Sun porch are shared spaces that includes a huge in-ground pool, beautiful screened in sun porch, outdoor dining, fire pit, hot tub, and the backyard is fully fenced in. The pool is closed, will reopen Early April. Laundry and Ev Charger can be used upon request for a fee.

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

The Hidden Shroom

The Hidden Shroom is nestled in the woods in a quite neighborhood within walking distance of Nashville. The space is pet friendly with a fenced in yard. Two bedrooms, one bath, full kitchen, outdoor patio with a hot tub & two person sauna. The apartment is in a finished basement with a private exterior entrance. Downtown Nashville is about a 15 minute walk and Hard Truth Hills, The north entrance to the Brown County State Park and the Brown County Music Center are all just a short drive away.

Bluegrass Country Cottage

Enjoy a quaint, private, quiet & charming little place to call your own, on a small, working (seasonal) Thoroughbred horse farm. Green acreage, lovely scenes and sunsets. Located in horse country, between historic Winstar Farm and Lane's End Farm, just a short drive to small town USA, Versailles; historic Midway; and to the nearby City of Lexington, home of the Kentucky Wildcats, Horse Capital of the World, Bourbon Country & so much more. Pets allowed (2 max), well behaved, pet fee applies.

YOUnique 3+ bedroom, spa/hot tub, huge deck

Our place is close to Indiana University, IU athletics, I-69/37 to Indianapolis, great views, family-friendly activities, nightlife, restaurants and dining. You’ll love our place because of the privacy - and the friendly neighbors (us), the beautiful outdoor space, the kitchen/great room, the hardwood floors, and the volleyball court and large yard. Our place is good for couples, solo adventurers, business travelers, families (with kids), big groups, and furry friends (pets - but no cats).

Guthrie Meadows Yellow Door Glamping Cabin

Easy access to the cabin with parking in front of the cabin for easy unloading. Our cabins have AC/Heat and MINI FRIDGE! The cabin is heated by an electric fireplace and cooled by an in wall air conditioner. Queen bed with fitted with mattress cover and fitted sheet. Blankets and pillows are provided by you. A dry sink are in each cabin as well as a mini fridge and coffee maker are provided. Fire pit is just outside the cabin along with private picnic table.

Swans Nest

If you are looking for a place to get away from the stresses of life this is it. You can fish on our 10 acres lake, walk thru the woods or just relax on the porch swing. Only 5 minutes from the nearest town, 30 minutes from Terre Haute and 40 minutes from Indy. Front porch faces a walnut tree grove and back porch faces 10 acre lake. At least 3 State Parks are within 20 miles of this property. Also super close to the Parke County Covered Bridge Festival.

Downtown Penthouse Loft- Free Parking & Elevator

A warm, comfortable downtown loft with garage parking — ideal for work trips, longer stays, or a quiet city escape. It’s a true city loft — open, airy, and easy to live in while still being right in the middle of everything. Located in a historic downtown building, the condo sits on a quiet residential floor, making it a calm, comfortable place to come back to after a day out. Secure garage parking and elevator access make coming and going simple

Luxury home in the heart of Indy

Relax in this luxury home, high-end family residence situated in the rejuvenated Bates Hendricks district of downtown Indianapolis. This is the same location where the HGTV show "Good Bones". Cheap Ubers or Lyfts anywhere downtown 1.6 miles from Convention Center, Lucas Oil, Pacers Stadium Countless restaurants and entertainment in Fountain Square, Mass Ave, and Downtown 1 Gig internet and Free Keurig Coffee A Two car garage and street parking