Holiday houses in Jackson County

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.

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.

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.

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.

Stay above a coffee shop @ The Urban Perk!

This stylish place to stay is perfect for group trips. Centrally located in the commercial historic district with a coffee shop downstairs! This apartment is walking distance from shops and restaurants downtown. The building was renovated in 2022, but the historic charm remains!