Vacation rentals in Jennings County

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Top-rated vacation rentals in Jennings County

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Top guest favorite

A landscaped courtyard is surrounded by a wooden fence, featuring vibrant flowers in shades of red, yellow, and white. A cozy seating area is visible on the stone patio, with a small table and chairs positioned in front of the flower bed.

Home in Vernon

5 out of 5 average rating, 41 reviews

Charming Historic Retreat Home

Encounter small-town hospitality and charm in this historic 1840s home in the quaint Town of Vernon. Our two-story brick home has all the modern amenities with a spacious central living room, cozy kitchen, private downstairs bedroom with sitting area and half-bath, and two upstairs bedrooms. Spend a relaxed evening around the courtyard firepit, or have some fun playing board games at the hand-crafted coffee table. Only a short walk to two restaurants, the town park, and the Muscatatuck River.

Top guest favorite

An exterior view of the reconstructed stone schoolhouse is shown, featuring a peaked roof and a large entry door. Two potted plants flank the entrance. A leafy tree provides shade on a grassy area, with open fields visible in the background under a clear blue sky.

Home in Versailles

4.95 out of 5 average rating, 154 reviews

School Days

Sharpen your pencils and reminisce about your childhood school days in this beautifully reconstructed schoolhouse. Built in 1879, this gorgeous property is situated just minutes from local coffee shops, locally owned restaurants, antique shops and the second largest State Park in Indiana. Be entertained with live music, museums, and other attractions by visiting three conveniently located cities. Come enjoy the modern amenities as well as the historical features this schoolhouse has to offer.

Superhost

Two patterned armchairs with a mix of textured fabrics are positioned facing a vibrant painting of a nature scene, framed in an ornate gold frame. The artwork depicts a serene landscape with a building beside a stream, set against a backdrop of trees.

Townhouse in Columbus

4.87 out of 5 average rating, 288 reviews

Walkable Cozy Downtown Studio (FREE Bikes to use)

Eat a relaxing breakfast with a view of 5 architectural monuments from the front porch or stroll to the numerous restaurants, coffee shops, or bakeries before you explore Columbus. Walk to everything from this stunning fully furnished private apartment in downtown Columbus with FREE off street parking. This remodeled cozy studio, originally built in 1865, features a stocked kitchenette, queen bed with linens, tub shower with linens, 50 inch smart tv with Netflix, and Wi-Fi. Bikes available

Guest favorite

A wooden deck overlooks a lush, green landscape with trees and a winding path. A metal planter sits on the deck, offering a space for gardening. Dappled sunlight filters through the leaves, creating a serene outdoor setting.

Cottage in Madison

4.86 out of 5 average rating, 162 reviews

Cozy Cottage downtown *Pets*Trails*firepit*Clean

Sue’s Cottage is a quaint two bedroom cottage with a porch over looking the Heritage Trail of Madison. It is perfect for pets. It is a home to many species of birds and wildlife. Relax on the deck bird watching or stroll through the heritage trail & scenic railroad tracks surrounding the cottage, which leads to the river walk. We are walking distance to all historic Madison offers. We are less than a mile from Clifty Park. A portion of each stay is donated to local charity.

Top guest favorite

A yurt is shown surrounded by expansive green grass under a clear blue sky. Contrails from passing aircraft create intersecting lines overhead, while sunlight shines brightly behind the structure, enhancing the tranquil outdoor setting.

Yurt in Madison

4.96 out of 5 average rating, 225 reviews

Madison's only Yurt experience!!!

You'll love this unique and romantic escape in the hills of southern Indiana! Located just 20 minutes from beautiful downtown Madison and Vevay. Enjoy the countryside in your very own yurt. Come relax after a hard day of shopping in downtown Madison or after a late night at Belterra casino. You will love the warm inviting boho style of decor while enjoy the beautiful sunsets from the deck. The stars look so close you could touch them from the grassy hillsides of this enchanting property.

Top guest favorite

A welcoming living area is centered around a wooden coffee table adorned with decorative items. Two comfortable sofas, equipped with cushions, invite relaxation. Natural light filters through windows, and a rustic ladder leans against the wall. A glimpse of the kitchen area can be seen in the background.

Cottage in Sunman

4.99 out of 5 average rating, 136 reviews

Phil’s Place, a comfy country cottage with hot-tub

You have found your secluded getaway from it all! Enjoy all the comforts of home in a quaint country setting. Extra amenities include a hot tub and a bottle of local wine to enjoy! Centrally located, visitors can easily explore all the Tri-state area has to offer, like Perfect North Slopes, Creation museum, antique markets, casinos, and festivals like Friendship muzzleloader shoot, Freudenfest, and Happy Valley Bluegrass. There are 3 wineries and 2 breweries all within 30 minutes!

Top guest favorite

The cabin exterior is softly illuminated by string lights, creating a warm ambiance. Wood siding complements the design, while tall windows enhance the visual appeal. A small patio area with chairs invites relaxation in the tranquil wooded setting.

Cabin in Madison

4.98 out of 5 average rating, 507 reviews

Cabin on the Ridge: The Sequel

Welcome to the area's first new construction short term rental tailored for you, the guest. This contemporary cabin is nestled in the woods right in the heart of Amish country. This is the perfect destination for those who want to getaway yet enjoy the unique beauty of Historic Downtown Madison (25 minutes) recognized as "The prettiest small town in the Midwest" or chase waterfalls at Clifty Falls State Park (25 minutes). •Fast wifi •Roku TV •Keurig (K-Cups Available)

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, 9 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.

Top guest favorite

An indoor pool area is showcased with a bright sky and floor-to-ceiling windows offering scenic views of the surrounding hills. The pool is surrounded by tiled flooring and potted plants, creating a serene setting. Skylights enhance the natural light within the space.

Apartment in Madison

4.99 out of 5 average rating, 156 reviews

The Treehouse - Hot Tub - Indoor Pool Get Away!

The Treehouse is a perfect retreat! It is secluded by the hills surrounding Madison. Complete privacy, yet 5 minutes from downtown, or hilltop. Year-round views of the beautiful hills of Kentucky. Winter views of the Ohio River and downtown. The house has stunning ceilings made from coastal cedar off an island near Vancouver, British Columbia and beautiful skylights in the studio and indoor pool area. This is an Adults only property. 2-night min.

Guest favorite

A modern living space features a black sofa positioned next to a wooden sliding door. A round white dining table with four chairs is set against a light-colored wall. Natural light fills the room, complemented by a textured area rug and a wooden bowl of fruit on the kitchen counter.

Apartment in Columbus

4.95 out of 5 average rating, 149 reviews

Cozy 1-Bedroom Retreat ~ New Remodel, Fast Wi-Fi

***** Most reviewed SUPERHOST in Columbus ***** Easy check-in with our guest portal—access codes, Wi-Fi, parking, and directions all in one place. Business guests can also download invoices hassle-free. Discover the perfect blend of comfort and convenience in this newly renovated 1-bedroom unit. Sleep soundly with a white noise machine. Ideal for both short and extended visits, enjoy a relaxing retreat within walking to Columbus's downtown charm.

Guest favorite

Home in Columbus

4.93 out of 5 average rating, 184 reviews

Reflections of Home

Kick back and enjoy all the amenities of home in this adorable, and conveniently located duplex situated in a quiet neighborhood. This duplex unit is located within minutes of architecturally diverse Columbus neighborhoods, close to Lincoln Park ball diamonds, biking and people trails are within a mile. The area has a wide variety of local dining favorites and is also 30 minutes from Brown County state park and Nashville.

Top guest favorite

A single-story home is shown, featuring a welcoming front porch with wooden benches. The yard is green and well-kept, with low shrubs and a stone pathway leading to the entrance. Trees provide shade, and the surrounding neighborhood is visible in the background.

Home in Columbus

4.95 out of 5 average rating, 546 reviews

Cozy Home - You'll Love This Place

Conveniently located across from Lincoln Park Ball Diamonds & Hamilton Ice Center, and just blocks from Columbus Regional Hospital & Nexus Park. Close to restaurants and local activities. This comfortable, welcoming home is in a safe neighborhood and well-stocked with everything you might need. As a frequent traveler myself, I’ve done my best to think of all the essentials so you can relax and enjoy your stay.