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Cottage holiday rentals in Southern Indiana

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Top-rated cottage rentals in Southern Indiana

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Guest favourite
Cottage in Hudson
4.95 out of 5 average rating, 125 reviews

Hot Tub, Large game area, Ready for the holidays!

Cozy 3 bed 2 bath home nestled right along the banks of Rough River with little boat traffic. A community boat ramp is conveniently located behind house and the main lake is only a 15 min boat ride away. Only a short drive to the beaches of Rough River State Park. Plenty of sleeping area with King and Queen bedrooms and a Bunk room with 5 twin beds. The oversized garage will store a boat or kayaks while you visit. Enjoy a game of ping pong, pool or cozy up by the firepit!! Perfect for fishing!!

Top Guest favourite
The image shows a well-kept lawn leading to a tranquil, reflective pond. A simple single-story house is positioned to the left, with a driveway visible. Lush green trees surround the area, creating a serene atmosphere.
Cottage in Brookville
4.98 out of 5 average rating, 102 reviews

Secluded Wooded Getaway w/ 2BR 2BA + Private Lake

Enjoy a weekend getaway at this cozy homestead nestled on 40 acres of wooded land with biking, hiking, walking trails and its very own stocked private lake & pedal boat. Take a break and relax on the dock or by the fire pit as you & your family & friends go off the grid... take a short drive to the quaint downtown Brookville, go experience the beautiful Brookville Lake & golf course, even check out the Wolf Habitat & Canoe Rental location right down the road. This is just the escape you need!

Top Guest favourite
The charming yellow cottage features a covered front porch with two black chairs, inviting relaxation. Neatly trimmed hedges line the walkway, leading up to the front door, which is adorned with a decorative wreath. A spacious lawn and a clear blue sky enhance the warm appearance.
Cottage in Bardstown
4.99 out of 5 average rating, 444 reviews

The Cottage Circa 1898 Downtown Location

Charming 1800's cottage listed on the National Register of Historic Places in Bardstown. Voted Most Beautiful Small Town in America. Walking distance from downtown shopping, nightlife, dining, and local attractions. Located along the Kentucky Bourbon Trail. I love Bardstown and wanted my cottage to look and feel like what is best about the town- historical charm mixed with modern amenities. Clean, cozy and comfortable; it is a space that I hope you find enjoyable while visiting Bardstown.

Top Guest favourite
An exterior view of a modern studio is presented, showcasing a dark exterior surrounded by lush greenery. Two bright red chairs are positioned at the entrance beside twin planters, and a statue is seen on the ground. Trash bins are discreetly placed to the side.
Cottage in Bloomington
4.97 out of 5 average rating, 270 reviews

Relaxing Retreat in the Woods

Relaxing retreat on 16 acres of woods , minutes from shopping, restaurants, Lake Monroe and the I.U. stadium--a 13 minute drive for basketball and football fans. Fire pit, grill, hammock, board games, kitchenette, CD, record player. No cable /television. Cell phone service and internet available if sometimes a bit spotty. The studio is in the woods so you may see or encounter wildlife including deer, opossums, raccoons, snakes, bobcats, coyotes and birds. Owner lives on property.

Guest favourite
Cottage in Madison
4.86 out of 5 average rating, 170 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 favourite
The exterior of a renovated two-story home is featured, showcasing a distinct architectural design with exposed beams. Large windows allow natural light to enter, while a welcoming front door is framed by decorative lighting fixtures. A concrete pathway leads to the entrance.
Cottage in Owensboro
4.97 out of 5 average rating, 159 reviews

The Woodford Retreat Cottage

Take it easy at this unique getaway.. Completely renovated 2,000 sq ft home with a beautiful river view, 3 bedrooms, 2 family rooms, 2 full bathrooms, fully stocked kitchen. The back yard is fenced with a deck, patio table and glider. This property is located a few blocks from the Owensboro Convention Center, Bluegrass museum, and multiple downtown restaurants. This property adjoins English park. Excellent rental for a weekend of downtown adventures or just enjoying the river view.

Top Guest favourite
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, 140 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 favourite
A light and airy living area features a gray sofa adorned with an orange throw pillow. A large area rug integrates various colors and patterns. Two armchairs and a plush ottoman provide additional seating, while a TV console holds a collection of books. Natural light filters in through the windows.
Cottage in Dry Ridge
4.99 out of 5 average rating, 322 reviews

Stylish Bluegrass Cottage 7 min to Ark - Fire Pit!

Built in 1954, stylish Bluegrass Cottage has been recently renovated and modernized for your comfort and is located 7 minutes from the Ark, and 37 minutes from the Creation Museum!  Centrally located - 2 minutes away from Walmart and multiple restaurants, but still has plenty of privacy with a privacy fenced back yard, and your own propane fire pit! You'll enjoy access through the back gate to the local park with a walking path around the lake, perfect for evening strolls!

Top Guest favourite
A wooden deck leads to the entrance of the cottage, surrounded by lush greenery. A concrete patio features a circular table with benches, providing a shaded outdoor space. The natural setting creates a serene environment, with trees framing the view.
Cottage in Hodgenville
4.98 out of 5 average rating, 238 reviews

Basil Cottage on the Creek

The Basil (baz-el) cottage is the perfect get-a-way where you can sit on the back porch sipping coffee while overlooking the babbling creek- get back in touch with nature for a much needed break from the stress of every day life. It may be a much needed romantic weekend, a mid- way point as you tour the bourbon trail, visiting Lincoln's childhood home or just a place of your own while in town to visit family, no matter what brings you to our cottage- you will love it here.

Top Guest favourite
The front exterior of the vibrant yellow cottage is framed by a white picket fence. A welcoming red door is centered beneath the front porch, which is supported by white columns. Lush green grass lays in the yard, with two hanging planters on either side of the door.
Cottage in New Harmony
4.99 out of 5 average rating, 108 reviews

Honeycomb Hideaway

Welcome to Honeycomb Hideaway, a vibrant yellow cottage nestled in the heart of historic New Harmony, Indiana. Our cozy one-bedroom retreat offers a peaceful and exciting escape, just steps away from Murphy Park, fantastic restaurants, and captivating tourist activities. Immerse yourself in New Harmony's rich heritage, exploring charming streets, unique shops, and art galleries. Indulge in local cuisine or embark on outdoor adventures in parks and walking trails.

Top Guest favourite
A comfortable living room is presented with a light grey sectional couch and a white coffee table atop a soft area rug. A flat-screen television is positioned on a wooden stand. Natural light enters through the window with blinds, enhancing the calm atmosphere.
Cottage in Terre Haute
4.97 out of 5 average rating, 112 reviews

Lyndsay's Cottage

This unique place has a style all its own. This house is fully furnished with nicely refinished hardwood floors. There are two bedrooms with queen sized beds and plenty of storage and room darkening blinds. There is a Washer & Dryer downstairs and a game room for the kids. Couch in living room is able to pull out into bed and there is a futon in the game room downstairs. Backyard is fully fenced. Close to Union Hospital, ISU and many local restaurants and shops.

Guest favourite
A cozy kitchen area is highlighted, featuring dark cabinetry and modern stainless appliances. A large island made of reclaimed wood with stools for four sits in the foreground. Light streams in through a window, complementing the rustic decor and butcher block counters.
Cottage in Madison
4.9 out of 5 average rating, 199 reviews

Cozy Farmhouse Retreat in Historic District

Located in the Historic District in Madison! Lisa and Richard co-own and co-host this recently updated cottage. Welcome to our cozy, chic Farmhouse Retreat. It is one block from Main Street, featuring so many charming shops, restaurants, and historic buildings for which Madison is famous. Only three blocks from the mighty Ohio and a short five-minute drive to Clifty Falls State Park. We fell in love with Madison and know you will, too.

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