Vacation rentals in Jackson County

Schitt’s Cabin

Experience the novelty and delight of rural living in a charming log cabin on a hill in the forest. Nicknamed “Schitt’s Cabin” because of the charm and Schitt’s Creek references, “The Cabin” is your favorite cabin away from home. As in Episode 5, Season 1 of Schitt’s Creek, you’ll be surprised in more ways than one by our charm and you’ll have the entire place to yourself— inside and out! The cabin is nestled on 6 acres of forests and sits remote atop a hill. Cell phone signal here is spotty.

Madison’s guest house

Built to show my daughter responsibilities and help traveling family with places to stay! Located close to popular restaurants such as Vat & barrel, brewskies, on the rox, poplar st. Rails, and many more! Almost everything in this guest house is brand new! It features wifi, Alexa, prime tv, and YouTube tv Digital keypad entry means you never have to even interact with anyone upon booking! We are also friendly and know the best hang outs and specials! Air queen bed available for living room!

Mellencamp boyhood home

Take it easy at this unique and tranquil getaway. It was a rental since 1979 and not many physical changes since that time. Authentic and vintage. to when John grew up there. The window in the basement is the same window he would sneak out of. The doors are the same doors he saw and used. Brand new beds, couches, TV. Appliances are not new but not vintage either. Kitchen cabinets are vintage. Same doors he used. Bathroom throne is brand new. sink and shower newer, new sewer to the street.

Hollow Creek Getaway

Relax with the whole family at this peaceful, secluded location. Enjoy access to over 2,000 acres of public land with hiking trails, mountain bike trails, scenic views, kayaking, fishing & hunting (in season). The cabin offers 3 bedrooms with 2 full bathrooms and 2 living areas on separate levels. Air hockey, fooseball indoors; front porch and back patio with grill and outdoor seating. Fire pit area for bonfires. Creek to fish and play in. Private setting with cabin 1/4 mile off the road.

Fox Den Retreat Cabin

No PETS ALLOWED of any Kind, relax in peace, at this unique and tranquil getaway. nature abounds with the flight of Hummingbirds, Butterflies, Birds and the peaceful and tranquil ambiance of a remote nature cabin. with plenty of places and things to do within 5 to 30 minutes of the cabin. Hike the Knob Stone trail all the way to Kentucky. Parks, Speedway, Drag Strip, Golf at Western Hills golf club. swim, Boat, fish at Delaney Park 5 minutes away, 10 minutes to Starve Hollow State Park.

Come downtown to the green haven

Enjoy a relaxing stroll through downtown, where great food, fantastic coffee, and friendly locals await. Our newly listed apartment is perfectly situated just steps away from some of Seymour’s best eateries, shops, and boutiques. Whether you’re craving a bite to eat, looking to browse unique stores, or simply want to soak in the charm of the neighborhood, everything is within easy walking distance. You’ll love the area and feel right at home during your stay. We can’t wait to host you.

Smalltown Living Apartment 1

Keep it simple at this peaceful and centrally located apartment in a safe area in the heart of Seymour, Indiana. The Smalltown Living apartment offers a quiet space to unwind. Kitchen furnished with everything needed to cook or take a short stroll to the downtown area to dine at one of the restaurants. Coffee shops, boutiques and more all conveniently located nearby. Free WiFi and Roku TV provided along with access to free laundry facility. Convenient free parking.

Centrally Located Home Downtown

Enjoy your stay in the heart of downtown Seymour! This home is perfect for anyone looking for a comfortable and convenient stay. Enjoy a cozy, quiet atmosphere while being just minutes from local restaurants, shops, and parks. For groups of 7-8 people: The couches shown in the photos will be replaced in early November to accommodate larger groups. A convertible sectional will be added to the living room to provide another queen-size sleeping option.

Seclusion at it's best! Private lake and cabin.

This remote location in south-central Indiana is perfect for someone looking for total seclusion. Make sure to grab your groceries on the way out. The 3 bedroom/2 bath cabin is situated in the middle of 370 private wooded acres on a 14 acre lake exclusively for your enjoyment. Bring your fishing gear or feel free to use ours. There are miles of trails and logging roads to roam and explore. Help yourself to hunt mushrooms while in season.

Cozy glamper with scenic pond

Welcome to Stout Hill Haven 🌅 Your storybook hideaway nestled next to a sparkling 2.25 acre pond. Our 2025 Timberwolf 20OG features a loft with a fireplace, a kitchenette, & room for 4. Sip coffee on the porch or roast marshmallows under the stars. Whether you’re listening to the frogs sing by the pond, watching sparks dance into the night, or simply curling up with your favorite book, this haven was made for wonder + sweet memories.

3BR/3BA Peaceful Retreat - Fire pit & Game room

HIGHLIGHTS: Cozy Indoor Fireplace Fire pit and outdoor seating/porch swing Fully stocked kitchen High-speed Wi-Fi and smart TVs Infinity game table Washer and Dryer 3 Full bathrooms Escape to serenity at this barndominium nestled in rolling hills, woods, and open fields in the heart of southern Indiana. This modern retreat offers the perfect getaway for families, couples, or small groups seeking privacy and adventure.

Spacious loft in downtown Seymour!

Everything you'll need and more. This is a large, quiet space right in downtown Seymour. And, guests have complete privacy. No one else lives here. This loft has more than 1400 square feet... and is perfect for up to four guests. Both beds have luxurious Serta iComfort memory foam mattresses. There's also a full kitchen and several restaurants within easy walking distance.