Holiday houses 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 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, 110 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

ValueFamilyHospitality

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, 118 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, or find inspiration. With 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.

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Superhost

Apartment in Mooresville

4.82 out of 5 average rating, 237 reviews

Apartment near Indianapolis airport

This is one of 4 apartments in large house sitting on 2 acres in the small town of Mooresville. We are conveniently located 7.1 miles from Indianapolis International Airport 18 miles from downtown Indianapolis 17 miles from Indianapolis Convention Center 35 miles from Indiana University in Bloomington. This apartment is upstairs. This house is not suitable for children under 12. If interested in booking, please answer our pre-booking questions found at the beginning of House Rules.

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Top Guest favourite

Home in Coatesville

5.0 out of 5 average rating, 51 reviews

Peaceful, Stunning A-Frame Home near hiking trails

Welcome to our beautiful family-friendly home, located 35 min west of Indianapolis, 20 min from Depauw University, and 40 min from Turkey Run. Nestled in a safe and quiet neighborhood, our property offers the perfect blend of relaxation and accessibility to the some of the best hiking Indiana has to offer. As you come into this peaceful setting, enjoy the time on our front deck while watching the sunrise. We love hosting families with kids or groups of friends looking to disconnect.

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Top Guest favourite

Cabin in Unionville

5.0 out of 5 average rating, 218 reviews

Elevated Wilderness | Mindful Retreat | 2 Kings

Executive Forest Sanctuary/2 King Beds, Hot Tub & Trails Escape to an architectural masterpiece set on 40 wooded acres. Designed for professionals, couples, and active adults seeking a high-end nature reset, Cabin Porch Paradise balances 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 ridge top retreat.

ValueFamilyAccess

Top Guest favourite

A historic farmhouse with a large wrap-around screened-in porch is set against a backdrop of autumn leaves. A gravel pathway leads to the main entrance, and several white Adirondack chairs are positioned on the lawn, inviting guests to relax and enjoy the surroundings.

Home in Greencastle

5.0 out of 5 average rating, 38 reviews

Authentic Family Farmhouse on Pond / Greencastle

Family Farmhouse surrounded by woods & crop fields, an expansive lawn, pond, screened-in porch, fire pit and historic barn. 10 min. to downtown Greencastle & DePauw/35 min. to IND airport. Ideal for a multi-generational family or friends gathering for special events.Adjacent guesthouse can be reserved to sleep 4 more. Fishing poles, yard & board games provided. Children are welcome, but please send inquiry to hosts about safety concerns for little ones before reserving.

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Top Guest favourite

A lakefront house in warm golden tones is depicted among tall, leafy trees. The property features a two-car garage, a gravel driveway, and a prominent walkway leading to the entrance, with scenic views of the lake visible in the background.

Cabin in Rockville

4.99 out of 5 average rating, 101 reviews

Classic Lakefront Retreat on Raccoon Lake, USA

Your dream lakefront retreat on Raccoon Lake awaits! This 3,800 sqft lake house is screaming with character - exposed timber beams and serene views are just the beginning of what this mid-century vacation home has to offer. Enjoy traditional charm combined with modern amenities and conveniences like 1Gb fiber internet. This vacation home is lakefront, with private access to a private dock where guests can dock a boat. Parties not permitted. Registered guests only.

ValueFamilyOutdoor spaces

Guest favourite

A serene countryside landscape is captured at sunset, featuring a lush green field with round hay bales scattered throughout. The sun is setting, casting a warm glow over the expansive horizon, with trees lining the perimeter, providing a peaceful backdrop.

Farm stay in Danville

4.85 out of 5 average rating, 86 reviews

The Hobbit's Shire on 32 acres near Indianapolis

Welcome to our charming Hobbit’s Shire! Nestled in the countryside, this retreat offers a peaceful and relaxing getaway while still being located close to Indy!!! Enjoy our large backyard and sip your morning coffee on the patio while watching the sunrise or for a wonderful wine experience overlooking the backyard. Book your stay with us for a peaceful retreat or family getaway or an adventure filled vacation and create lasting memories.

ValueFamilyKitchen

Guest favourite

A spacious heated pool is surrounded by lounge chairs and umbrellas, set in a lush garden area. The inviting pool features a fountain, while the deck offers ample seating for relaxation. A cozy living space features comfortable seating, a flat-screen TV, and a dining table amid warm wood accents.

Home in Poland

4.94 out of 5 average rating, 140 reviews

Captain Bill’s Lake House Heated Salt Water Pool

Captain Bill’s Lake House. This majestic A-frame is at the entrance to the Cataract Lake boat ramp. The house will accommodate up to 7 guests, with three bedrooms and two full baths. All guests have full access to Captain Bill’s shared heated salt water pool and surrounding gardens. Boat parking is available on the property, inquire for details. Heated Salt Water Pool is seasonal beginning May 1, through September 30th.

LocationFamilyDecor

Top Guest favourite

Loft in Mooresville

5.0 out of 5 average rating, 443 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!

LocationValueQuiet

Top Guest favourite

A charming two-story house is depicted, featuring light grey siding and a welcoming front porch. The well-maintained garden displays vibrant flowers and lush green grass. Concrete steps lead to the entrance, framed by soft greenery. The cloudy sky adds a serene backdrop to the scene.

Home in Greencastle

5.0 out of 5 average rating, 17 reviews

Haven on Hanna

Welcome to Haven on Hanna — your home base for campus visits, alumni weekends, or quiet getaways in the heart of Greencastle. Just steps from DePauw University and downtown, this spacious 3-bedroom, 4-bath home blends historic character with sleek, modern finishes. Sip coffee on the back patio, stroll to events at DePauw, and experience the best of small-town comfort with big hospitality.

LocationFamilyKitchen

Top Guest favourite

A compact kitchenette is visible, featuring a stainless-steel refrigerator and microwave positioned above a counter with a coffee maker. Soft lighting from a lamp illuminates the nearby bedroom area, where a bed is dressed in neutral linens, enhancing the calming ambiance.

Apartment in Greencastle

4.99 out of 5 average rating, 415 reviews

Charming apartment on the edge of DePauw campus.

After traveling around the world ourselves we know what its like to have a peaceful place to land and unwind. This apartment was designed with that in mind. We have been hosted by some of the finest people around the world and we desire to return the favor to those traveling through our lovely hometown.

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