Vacation rentals in Jackson County

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Top-rated vacation rentals in Jackson County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Superhost

The two-story log cabin is nestled among trees, featuring a front porch with two rocking chairs. A grassy area surrounds the cabin, complemented by wooden lattice details along the base and large windows that invite natural light.

Cabin in Bedford

4.83 out of 5 average rating, 63 reviews

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.

A serene bedroom features a spacious bed with a light-colored duvet and matching pillows. Soft sunlight filters through sheer curtains, illuminating the room. A framed picture rests on a bedside table, while decorative wall art enhances the calming atmosphere.

Guesthouse in Seymour

4.5 out of 5 average rating, 12 reviews

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!

Cabin in Norman

New place to stay

Moto Supreme - Group-Ready Cabins on Trails!

Moto Supreme: a one-of-a-kind 174-acre getaway. 3 cabins, 13 beds, sleeps ~20. Two cabins w/ kitchens & full baths; central bar cabin w/ neon-lit lounge & half bath. Trails for motorsports, hiking & biking, plus fire pit, grill, & picnic tables. This place has been the best off-roading in the midwest for 30 years. Now completely private! Knobstone Trail runs through property; near Hoosier Forest & Lake Monroe. Perfect for reunions, events, or holidays. Featured on YouTube—search Moto Supreme.

Top guest favorite

A single-story brick house is presented with a wide concrete driveway leading to a garage on the left. Porches feature two sets of steps and classic black shutters on several windows, surrounded by a small lawn and mature trees in the background.

Home in Seymour

4.88 out of 5 average rating, 82 reviews

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.

Top guest favorite

A serene cabin is nestled among lush green trees, featuring a sloped roof and large front windows. The welcoming front porch is flanked by a gravel pathway, leading to an entry door. A wooden fence encloses the property, enhancing the sense of privacy.

Home in Vallonia

4.98 out of 5 average rating, 46 reviews

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.

Top guest favorite

A charming cabin exterior is showcased with a green metal roof and wooden log siding. Soft lighting highlights the entrance, adorned with nature-inspired decorations and plants. The paved driveway leads to the front door, creating an inviting approach amidst the natural surroundings.

Cabin in Salem

5 out of 5 average rating, 16 reviews

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.

Top guest favorite

A modern kitchen features a central island with a double sink and seating for four. Light wood cabinetry is complemented by white appliances. Exposed brick walls add texture, while decorative plants bring a touch of greenery. Warm lighting is provided by pendant lights overhead.

Apartment in Seymour

5 out of 5 average rating, 72 reviews

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.

Guest favorite

A living area features a dark blue sofa adorned with two yellow pillows, paired with a reclining chair. The space is illuminated by natural light through a large window, and a kitchen area is visible in the background, containing a white stove.

Apartment in Seymour

5 out of 5 average rating, 8 reviews

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.

Superhost

A charming two-story house is visible, featuring a front porch and a set of steps leading to the entrance. The yard is covered with fallen leaves, and large windows allow natural light to brighten the space.

Home in Seymour

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.

Guest favorite

A wooden cabin is seen next to a serene lake, surrounded by lush green trees. The water reflects the calm landscape, and a wooden dock extends from the bank, offering access to the lake.

Cabin in Medora

4.94 out of 5 average rating, 124 reviews

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.

Top guest favorite

A modern camper is displayed in a green outdoor setting. Large windows allow natural light to enter, while a small covered porch invites relaxation. Steps lead to the entrance, surrounded by neatly trimmed shrubs and a gravel path, highlighting the rustic charm of the space.

Camper/RV in Brownstown

4.83 out of 5 average rating, 23 reviews

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.

Guest favorite

An outdoor fire pit area features six black Adirondack chairs arranged around a central fire pit. The setting includes a backdrop of gently rolling hills and a covered porch area, illuminated by warm evening light under a colorful sky at sunset.

Home in Vallonia

5 out of 5 average rating, 8 reviews

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.