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
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 out of 5 average rating, 57 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
Cabin in Unionville
5 out of 5 average rating, 209 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 dining area features a round wooden table surrounded by transparent chairs, complemented by plush white seat covers. A modern chandelier hangs from the ceiling, illuminating the space. The room showcases a combination of hardwood flooring and black accent walls, with large sliding glass doors leading outdoors.
Home in Greencastle
4.98 out of 5 average rating, 106 reviews

Modern 4 Bed Home On Golf Course Close To Campus +

4 bedroom, 2 bath-master w/shower guest ba w/tub & shower ranch home w/ 5th hole of the golf course as your view & literally steps from patio! Minutes from campus, restaurants & shopping. Quiet established neighborhood. (1) King bdrm, (2) bdrms w/full bed and (1) office/bedroom w/fold down couch. -Blackout curtains -Wifi -Spacious family room w/smart 75 in TV -Close to everything Outdoor patio w/furniture to enjoy the golf course views. Depauw themed basement w/ sauna, pool & poker tables

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
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, 107 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

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, 125 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, 76 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
The kitchen area features a central wooden island with seating and ample natural light coming through multiple windows, showcasing views of the surrounding greenery. A modern refrigerator and stove are present, along with decorative elements that add character to the room.
Bungalow in Plainfield
4.94 out of 5 average rating, 90 reviews

Modern Bungalow-Near Airport/Indianapolis

Relax, escape the kids, step up your business travel, or "work from home" in this modern private bungalow with a luxurious touch. Enjoy a nice evening on the private dock or porch while listening to the crickets and bullfrogs. Have a night out at one of our favorite spots and retreat back to your quiet private oasis while you sleep in comfort on our 1000 count, 100% Egyptian cotton sheets. Conveniently located 10-15 minutes from the airport and 20-25 minutes from downtown Indianapolis.

Guest favourite
Cabin in Poland
4.98 out of 5 average rating, 44 reviews

Cozy Lofted Cabin (#3) at Cataract Lake Getaway

This new cabin on a private road is a serene setting perfectly blending rustic charm and modern comfort. Only a half-mile from Cataract Lake, quick and easy access to boating, fishing, kayaking, etc. awaits! Numerous nearby attractions are sure to provide great experiences (Cataract Falls, C Bar C Event Center, Exotic Feline Rescue Center, state parks, brewery/winery, local shops/eateries, etc.) And of course, simply enjoying time in and around the cabin itself is a fulfilling getaway!

Top guest favourite
The entrance to the cabin features a covered porch with rustic wooden supports and decorative string lights. A welcoming outdoor seating area is visible in the background, surrounded by lush greenery and shaded by nearby trees. The path is lined with stones and small plants.
Cabin in Unionville
5 out of 5 average rating, 504 reviews

Cozy Cabin Close to University 1

The Red Rabbit Inn is located just 15 mins from the Indiana University campus and just 20 mins from Nashville, IN , this architecturally designed cabin features the works of local artisans. Beautifully landscaped on a secluded, wooded pond, this cabin includes a loft bedroom with KING bed, bath, full kitchen, gas fireplace, TV & Wifi, with your own private deck, outdoor hot tub, fire pit area & gas grill. Cabin sleeps 2 guests. Located near Lake Lemon, in a beautiful serene setting.

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, 114 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 sweet-smelling poplar walls, the cabin offers a full bed by a picture window, small TV, writer's desk/library, AC, 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 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 out of 5 average rating, 523 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.

Popular amenities for Stilesville holiday rentals

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