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.

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 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).

12 Guest/Top Area /Families/Park

Welcome to our Family Airbnb 1- Great Location in residential neighborhood 2- 20 Min to Kentucky Derby Museum 3 - 20 Min to Louisville Mega Caverns 4- 15 Min Evan William Bourbon 5- 20 Min Churchill Down 6- Designed for 2 guests (3 Queen Bed, 1 double Bunk bed, 1 Queen Air Mattress) 7- Free Parking (2 Cars Inside and 2 Cars Outside) 8- Fully Equipped Kitchen 9- Fast Wi-Fi 10- Quiet and Safe Area 11- Private Patio 12-24/7 Available Host 13- 2 Smart TVs 14- Laundry In Unit

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.

"The Love Shack" Rustic Cabin Getaway

Cabin and/or camper spot, with 30 amp electric & hydrant water. Cabin has 1 full bed, bunk beds (max 4, bring your own linens, firm mattresses) equipped with AC/heat & mini fridge. Indiana's best keep secret - The Love Shack - nestled down a long lane in between 2 fields in rural Economy Indiana with pond & 3 acres to yourself. Started by my grandpa Tom Bond in 2000 and loved by all that visit. Follow us on social media. 2.5 miles to Cardinal greenway.

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

The Rickhouse ~ NULU ~ Bourbon Enthusiast’s Oasis!

Rickhouse: A structure designed to store and age distilled spirits. Sparked from a passion for fine spirits and the idea that a home can contain all the makings to craft the perfect cocktail, the Rickhouse was born. Featuring chesterfield leather seating, a vast collection of cocktail glasses, regulated 4-tier humidor and spirits-centric art, it strikes the perfect match of comfort and eccentricity. Cheers and enjoy The Rickhouse!