Holiday rentals in Stilesville

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Top-rated holiday rentals in Stilesville

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

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Top guest favourite
Cabin in Unionville
5.0 out of 5 average rating, 211 reviews

Elevated Wilderness | Mindful Retreat | 2 Kings

Executive Forest Sanctuary/2 King Beds, Hot Tub & Trails Escape to an architectural masterpiece set on 40 private, wooded acres. Designed for professionals, couples, and active adults seeking a high-end nature reset, Cabin Porch Paradise balances complete seclusion with proximity to Southern Indiana’s best destinations. Whether you are unwinding in the spa amenities, working remotely via high-speed fiber, or exploring the surrounding lakes and state parks, this is your ultimate ridgetop retreat.

Top guest favourite
A spacious modern structure is set against a clear blue sky, featuring a hip roof and large windows that allow natural light to fill the interior. The exterior is accented by stone pillars and a wide porch, surrounded by a grassy field.
Home in Greencastle
5.0 out of 5 average rating, 58 reviews

Quiet Country Retreat Near DePauw University

Discover the charm of Throttle Back Ranch, a brand-new (2023) home just minutes from Greencastle, DePauw University, Cataract Falls State Park, Putnam Park Road Course, and Cowpokes Arena. Racing enthusiasts will love our unique touch - a full-size race car mounted on the wall! Enjoy country living at its best, with a fully equipped kitchen, entertainment options, and an expansive covered porch for breathtaking sunset views. Feel free to reach out with questions. We can't wait to host you!

Top guest favourite
The entrance is accessed by a set of wooden stairs featuring a metal railing. A door with large windows is flanked by potted plants, providing a welcoming touch. Natural light filters through the greenery surrounding the entrance.
Guest suite in Indianapolis
4.99 out of 5 average rating, 108 reviews

A little secret hideaway

Keep it simple at this peaceful and centrally-located place. It’s close to everything, making it easy to plan your visit. It’s close to the airport, sporting events, and downtown. It’s up on the second level, but separate from the downstairs living. It has its own entrance and living space. 2.3 miles to Indianapolis airport 5.1 miles to Lucas Oil IRP 5.3 miles to Indianapolis Motor Speedway 8.3 miles to Lucas Oil Stadium 8.8 miles to Gainbridge Fieldhouse 8.8 miles to Indianapolis Downtown

Top guest favourite
A shaded porch area is visible, featuring several turquoise chairs arranged closely together along a concrete path. Lush greenery and blooming flowers frame the scene, offering a serene outdoor space conducive to relaxation.
Barn in Greencastle
4.92 out of 5 average rating, 65 reviews

Come Live The Barn Life In Town!

1 bed 1 bath unique red barn w/ sleeper couch + air mattress to accommodate up to 5 people! Experience the slow pace of the country life 3.6 miles from Depauw University. Imagine the peace & quiet from this location while roasting smore's in the chimenea from the front porch, but a quick 2.2 mile drive to all the restaurants and shopping! Features -Wifi -Washer/Dryer -Kitchenette -Coffee Bar -Walk In Shower (handicap accessible) -Air Mattress -Pull Out Sofa Bed -Walk In Closet -Keyless Entry

Top guest favourite
A charming one-room cabin features a wooden exterior with a green metal roof. Two blue chairs are placed on the small porch beside a door, which invites guests to enjoy the surrounding greenery in a tranquil setting.
Cabin in Bainbridge
4.94 out of 5 average rating, 115 reviews

Covered Bridge Cabin (on Big Walnut Creek)

Retreat and renew in this charming one-room cabin right by Big Walnut Creek and Baker's Camp Covered Bridge. Fish, kayak, or swim; hike or birdwatch in a nearby preserve; read, write, find inspiration. With its raw poplar walls, the cabin offers a full-sized bed by a picture window, small TV, writer's desk/library, air conditioning, fans, baseboard heat, kitchenette, toilet, sink, outdoor shower (before first frost), small porch, grill, and a fire pit. (No wifi in cabin!) Simple and beautiful.

Guest favourite
A wooden pathway leads from the cottage towards the water's edge, bordered by lush greenery. The peaceful lake is visible, framed by trees, creating a serene and natural setting. The pathway is designed with railings and is surrounded by grass and foliage.
Cabin in Monrovia
4.95 out of 5 average rating, 126 reviews

Waterfront getaway *cozy & peaceful*fishing*swings

Welcome to your peaceful lakeside getaway! This renovated boho-style cottage offers a quiet and laidback retreat. Featuring an open loft layout, a covered porch, and a large deck overlooking two small serene lakes, this home is designed for relaxation. Enjoy evenings under the Pergola with swings or gather around the hillside firepit for unforgettable nights. Its location also makes it easy for you to get around. You're just: 10 min to I-70 hwy 20 mins to the airport 30 mins to Indy Downtown

Guest favourite
A charming cabin exterior is framed by lush green trees, featuring a welcoming front porch with wooden railings and potted plants. The entryway is accentuated by a round window and vibrant red door, providing a cozy entry point to the retreat.
Guest house in Martinsville
4.97 out of 5 average rating, 77 reviews

Get away in the woods ! Fire pit, Game room

You will love this cozy private retreat a short drive away from bigger town amenities. Heading into Martinsville for some lunch (or candy!), checking out the beautiful landscape for some walking/hiking at Morgan-Monroe State Forest. Hunters Honey Farm 4.3 mi. Cedar Creek Winery, Brewery, Distillery 20 mi. Morgan Monroe State Forest 20 mi. Martinsville Candy Kitchen 15 mi. Art Sanctuary of Indiana 15 mi. TraderBakers Flea Market 15mi. sit by the fire pit and roast marshmallows, game room !!

Top guest favourite
An exterior view of the home is captured, featuring a light gray facade and metal roof. Colorful flowers and pumpkins decorate the landscaped garden, complemented by a bench positioned under a tree. Neatly arranged windows provide an inviting look to the property.
Home in Gosport
4.98 out of 5 average rating, 169 reviews

Maria’s Haven

Welcome to “Maria’s Haven”💕 A beautiful cozy home in the heart of a beautiful small town. This home belonged to my mother, Maria, who passed away in 2020 to breast cancer. This home was truly her “Haven”. Take a walk to the local diner, museum, Gosport playground, local shops, or to our delicious Amish bakery. We are also just a few miles from the popular “Hilltop” restaurant as well as McCormicks Creek State Park. Our mission is to make you feel like you never even left home. ☺️

Guest favourite
A modern home is positioned on a hillside, featuring a sleek black exterior and large windows that allow for ample natural light. A balcony extends from the structure, providing outdoor seating and a view of the surrounding trees.
Cabin in Nashville
5.0 out of 5 average rating, 524 reviews

Modern Nashville Home in the Woods

Welcome to Plāhaus — a modern retreat tucked into the woods of Brown County. #1 Most-wishlisted Airbnb in Indiana per Airbnb Designed for solitude, relaxation, and connection with nature, Plāhaus blends modern architecture with peaceful surroundings. Take in the views from the balcony, gather around the firepit, or explore nearby Nashville’s shops and restaurants. Perfect for romantic getaways, family escapes, or simply recharging from everyday life.

Top guest favourite
A well-maintained lawn features neatly trimmed grass and flowering plants, with a lantern hanging from a decorative hook. The log home is visible in the background, surrounded by lush greenery and framed by mature trees, offering a serene and inviting outdoor space.
Home in Center Point
4.98 out of 5 average rating, 231 reviews

Birdwatching and Covered Bridge at the Lynch Lodge

Pam and Mark Lynch will greet you to the country life at the Lynch Lodge. Located in the heart of Covered Bridge country. Pam, is a potter, graphic designer and artist and has a little pottery gallery on site should you care to visit. Mark is an engineer. If the quiet country sounds like what you are looking for, you will find it here. Located just 5 miles off I-70 south of Brazil. Easy access to all Covered Bridge Locations.

Top guest favourite
Loft in Mooresville
5.0 out of 5 average rating, 432 reviews

Loft Apartment: Beautiful Farm and Country Views

This beautiful, over the garage private apartment is located in a wooded area across from our 94 acre farm. A very peaceful setting to wind down and enjoy the nature around you. Conveniently located 15 minutes from the airport and 30 minutes from downtown Indianapolis. A work space is also available that overlooks this beautiful farm!! Also perfect for couples or small families to enjoy some time in the country!

Top guest favourite
Home in Morgantown
4.96 out of 5 average rating, 255 reviews

Relaxation Station | Pond + Hot Tub + Pet-Friendly

Escape to a private 13-acre forest retreat in Brown County! This pet-friendly woodland bungalow features a private hot tub, two stocked fishing ponds with walking trails, and a cozy fireplace. Tucked away in the secluded hills yet located just minutes from downtown Nashville and Brown County State Park, it is the perfect nature getaway for couples, outdoor lovers, and furry friends.

Popular amenities for Stilesville holiday rentals

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  4. Hendricks County
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