Holiday rentals in Stilesville

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

Walker Getaway | A-Frame•Hot Tub•Decks•Lake•Hiking

Escape to Walker Getaway, an updated A-frame cabin on 5 private wooded acres w a creek, hot tub, fire pit and multi-level decks. Located across from Walker Boat Ramp and only 5 minutes from Raccoon Lake Beach. Use the provided Indiana State Park pass to explore nearby Turkey Run and Shades. Fully stocked and family-friendly, it’s perfect for couples, friends, or families looking to relax, recharge, and explore Parke County. Walker Getaway is where modern comfort meets Indiana’s natural beauty.

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.

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.

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.

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.

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.

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.

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.

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!

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.

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.