House holiday rentals in Greencastle

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.

5 out of 5 average rating, 49 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!

A cozy bedroom features a dark wood bed with clean linens and two pillows. A lamp sits on a nightstand beside the bed. A window with dark curtains allows natural light to filter in, and framed art is displayed on the wall.

4.98 out of 5 average rating, 123 reviews

Castle 853 - We aim to be the cleanest!

Very Clean, stylish and up-to-date, Bedford Stone, single level home. Fully furnished, all linens, towels, cookware included. Coffee and snacks are there for your stay. We are a 3 minute drive to DePauw University, Crown Industrial Park, and the Historic Downtown full of Fine Dining, Craft Beer & Wine, Music. 300 feet from People's Pathway. Located in the heart of Covered Bridge country. 40 minutes from Indianapolis including the International Airport and the Indianapolis 500 raceway.

4.97 out of 5 average rating, 149 reviews

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

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. ☺️

A dining area is featured with a dark wooden table surrounded by six chairs. Natural light enters through two windows, illuminating the space. The kitchen is visible in the background, fitted with white cabinetry and modern appliances.

4.94 out of 5 average rating, 105 reviews

Peaceful Ctry Home 1 ac. Wlk to 3FatLabs. 3BR 2BA

Peaceful country home near 3 Fat Labs and Depauw University. Situated on beautiful and quiet 1 acre lot with fire pit. Relax on the back deck and enjoy view, visit Oakalla covered bridge or hike at nearby Depauw nature trails. Home has en suite master with King bed and open floor plan. Kids room with bunk, toys and pack n play. Bathtub in 2nd bathroom. Enjoy large selection of DVDs and games for kids and adults. Satellite TV and internet. Washer/dryer. Only 3.5 miles to Depauw.

4.94 out of 5 average rating, 223 reviews

A well-appointed kitchen features modern appliances, including a black refrigerator, with wooden cabinetry providing ample storage. A large island with bar stools invites casual dining. Natural light fills the space through multi-paned windows, enhancing the warm wood tones of the decor.

Home in Poland

Captain Bill's Guest House/seasonal swimming pool

Welcome to Captain Bill's Guest Lodge at Cagels Mill Lake! This gorgeous home offers modern amenities in a countryside setting. Perfect for bikers, boaters, fisherman, and anyone looking to enjoy lake life. Our guests are welcome to join us poolside at the main house. Our private pool is open only to us and our listed guests at our two Airbnb units. We're located seconds from the boat ramp and a short drive to Cataract Falls and Lieber State Park. Pool is seasonal.

A spacious living area is illuminated by recessed lighting, featuring a large gray sectional sofa adorned with decorative pillows. A round wooden coffee table is centered on a textured area rug, while a television stands on a light wood console. The open layout connects to a dining area with modern seating.

4.96 out of 5 average rating, 23 reviews

Modern Cottage In Town

Enjoy a comfortable and relaxing experience at this centrally-located home just 0.4 miles from Depauw's campus! 2 bed, 1 bath adorable home walking distance to downtown, campus, restaurants & shopping. Quiet established neighborhood. Features (1) King bdrm, (1) quen bdrm -Blackout curtains -Wifi -Spacious family room w/smart TV -Close to everything Outdoor patio w/furniture to enjoy the peace & quiet The space Modern cottage home with a minimalist aesthetic.

4.93 out of 5 average rating, 363 reviews

A single-story home is displayed, featuring a light-colored exterior with a red metal roof. A spacious porch, equipped with seating, is visible at the front. Surrounding grass is neatly maintained, and trees provide natural shade nearby.

Home in Brazil

Swans Nest

If you are looking for a place to get away from the stresses of life this is it. You can fish on our 10 acres lake, walk thru the woods or just relax on the porch swing. Only 5 minutes from the nearest town, 30 minutes from Terre Haute and 40 minutes from Indy. Front porch faces a walnut tree grove and back porch faces 10 acre lake. At least 3 State Parks are within 20 miles of this property. Also super close to the Parke County Covered Bridge Festival.

An open concept living area features high ceilings with large windows overlooking the lake. Sofas are positioned around a round coffee table on a textured rug. A dining table for eight is visible in the background, complemented by a modern kitchen equipped with new appliances.

4.96 out of 5 average rating, 128 reviews

Luxury Lake House: Stay French Lake

This bright and airy 4 bedroom home is a destination getaway perfect for your family, friends, or business retreat. With new furniture, appliances, and décor this retreat is the perfect getaway or staycation for your leisure or business needs. Nearby Attractions: Queen of Terre Haute Casino, Griffin Bike Park, Fowler Park, Laverne Gibson Cross Country Course, Rose Hulman, Indiana State University, and The Mill Concert Venue

The home features a charming facade with a gabled roof and symmetrical design. Two American flags are displayed on the front. A well-maintained lawn surrounds the house, complemented by neatly trimmed shrubs. A inviting walkway leads to the entrance, flanked by wooden chairs.

4.98 out of 5 average rating, 194 reviews

The Monon Belle

Welcome to The Monon Belle, located at 522 East Washington Street in Greencastle, Indiana, the home of DePauw University. This neo-classical home was built in 1920 just blocks from Greencastle's historic Courthouse District. Its location is within easy walking distance to all points on the DePauw campus. This is the ideal home to gather with friends and family members while visiting DePauw and Greencastle.

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.

5 out of 5 average rating, 9 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.

The living area features a cozy seating arrangement with upholstered chairs and a plush couch. A large painting of an elephant adorns the wall above a wooden fireplace. Natural light fills the room through double windows that are framed by patterned curtains.

5 out of 5 average rating, 47 reviews

1860’s Art House

This adorable historic Greencastle home was built in the 1860’s and still has many original features. This listing is for the first floor of the duplex, and it’s been updated with art from Indiana artists and local antique stores. Location is ideal- two blocks from DePauw’s campus and one block from the downtown square. Walking distance to bars, restaurants, and local shops.

4.99 out of 5 average rating, 201 reviews

The barn-style home is surrounded by lush greenery, showcasing a large, covered porch with multiple outdoor chairs. A well-maintained lawn extends in front of the home, and trees provide a natural backdrop, highlighting the tranquil setting.

Home in Marshall

Luxury Custom Built Amish Barn Home at Turkey Run.

Directly across the street from the Turkey Run State Park Campground, this beautiful newer barn home is centrally located to hiking, canoeing, horseback riding, etc. Hike your own trails in the 13 acres of wood and ravines on the property, or relax on the huge covered porch. Turkey Run State Park is less than one mile away. Discount given for weekly stays.

Popular amenities for house rentals in Greencastle

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.84 out of 5 average rating, 51 reviews

LuxeVilla-Pool-GameZone-Sleeps14-Kid|PetFriendly

4.98 out of 5 average rating, 81 reviews

A spacious hot tub is illuminated with colorful lights against a backdrop of dark woods, creating an inviting atmosphere. The cover is partially lifted, revealing clean, clear water ready for enjoyment.

Home in Rosedale

The Getaway House with Hot Tub and Pool

Home in Jamestown

New place to stay

Hilltop Manor | Hideaway Estate w/ Pool & Theater

5 out of 5 average rating, 14 reviews

A two-story home with a welcoming facade is set on a manicured lawn. The exterior features a mix of light and dark siding, a covered front porch, and decorative landscaping. A two-car garage is visible, and the driveway provides ample parking space.

Home in Danville

New beautifully furnished home.

A spacious white two-story home is set among lush greenery, showcasing a large front yard with well-maintained grass. A wrap-around porch with white railings invites relaxation, while the driveway leads to a garage on the right. Trees and shrubs add to the natural surroundings.

4.95 out of 5 average rating, 75 reviews

Peaceful country home & pool near DePauw

New place to stay

Deer Run Lodge/Indoor Pool/Hot Tub/Sauna

Weekly house rentals

A serene lakeside view captures still waters reflecting colorful autumn trees and neighboring homes. A grassy area with a wooden dock borders the lake, inviting moments of relaxation and connection with nature.

4.91 out of 5 average rating, 43 reviews

Healing Waters Lakehouse

4.92 out of 5 average rating, 37 reviews

The Forest House is characterized by its charming exterior, featuring a light-colored façade and a welcoming front porch. Lush green grass and well-maintained bushes surround the house, complemented by mature trees offering shade. The peaceful setting highlights the home's inviting nature.

Home in Brazil

Forest House: Your Cozy Retreat in Brazil, Indiana

4.96 out of 5 average rating, 76 reviews

The image shows a large lakehouse nestled in a wooded area, featuring a sloping ramp leading up to its entrance. A white lounge chair is positioned on the wooden deck, surrounded by greenery, suggesting a serene environment for relaxation.

Home in Cloverdale

7 Bedroom Lake House with miles of Wooded Trails

A welcoming living space features a large flat-screen television mounted on a dark media console. A cozy gray sofa and armchair are arranged around a wooden coffee table. Natural light filters through the window, illuminating a potted plant in the corner.

5 out of 5 average rating, 41 reviews

Lovely Bungalow

An open living area features a spacious sofa facing a coffee table, with a kitchen visible in the background. Light streams in through the windows, illuminating the wood floors. A dining table is positioned near the kitchen, creating a welcoming space.

4.94 out of 5 average rating, 16 reviews

Charming Retreat Near DePauw & Indy Hotspots

A spacious living area is presented with a light gray sofa, accompanied by a coffee table and floor lamp. A medium-sized television is mounted on a wooden cabinet. Natural light enters through a window, and framed art decorates the walls, creating a welcoming atmosphere.

4.95 out of 5 average rating, 37 reviews

Aikman Place (Not Troy's)

4.91 out of 5 average rating, 34 reviews

A spacious deck overlooks the serene lake, complemented by comfortable seating arrangements. Two lounge chairs sit facing the water, while a fire pit is situated in the center. Soft lighting is strung overhead, and surrounding trees add a touch of green to the tranquil setting.

Home in Rockville

Lakeside Paradise: Raccoon Lake

4.69 out of 5 average rating, 32 reviews

A serene view of a calm lake surrounded by dense greenery is presented. Steps made of wood lead down toward the water's edge, while reflections of the vibrant trees and sky are visible on the lake's surface.

Home in Martinsville

Lakefront- Nestled In Nirvana

Private house rentals

A cozy living area features an orange sofa paired with a dark armchair and a coffee table. A wall-mounted television is positioned across from the seating, complementing the warm tones of the space. Natural light enters through a window adorned with white trim.

4.96 out of 5 average rating, 80 reviews

Stylish Home Near Rose-Hulman and ISU

4.9 out of 5 average rating, 63 reviews

A cozy two-story house is nestled among vibrant fall foliage, reflecting on the calm lake surface. The exterior features a light-colored siding and a green metal roof, while a wooden deck provides access to the tranquil surroundings.

Home in Martinsville

Newly remodeled Cozy home on private lake

A welcoming living area showcases a neutral color palette with a combination of leather and fabric seating. A large area rug anchors the space, and natural light floods in through a window adorned with light drapes. Decorative elements include a coffee table and wall art.

4.98 out of 5 average rating, 84 reviews

4 Bedroom Home In Terre Haute. ISU, Rose Hulman

4.88 out of 5 average rating, 8 reviews

A welcoming exterior view of a single-story home is captured, featuring a neatly manicured lawn and landscaping. The driveway leads to a garage with multiple doors. The front door is framed by tidy shrubs and small trees, creating an inviting entrance under a blue sky.

Home in Avon

Luxury 3 bedroom house in Avon

A modern kitchen equipped with white cabinetry and stainless steel appliances is shown. Countertops provide ample workspace, and a door leading outside is visible at the end of the room. Natural light enters through a window, creating an inviting environment.

4.94 out of 5 average rating, 54 reviews

Modern Terre Haute Getaway

4.95 out of 5 average rating, 39 reviews

An indoor sauna space is presented, featuring wooden paneling and a slatted wooden floor. The walls are equipped with red light therapy panels, and buttons for control are visible. A glass door provides access to this serene retreat, enhancing relaxation options.

Home in Marshall

Stacie’s Mom’s with Infrared Sauna & Fire Pit

4.96 out of 5 average rating, 27 reviews

A spacious home is depicted with a brick exterior and a welcoming front porch. The property is surrounded by well-maintained grass, with mature trees in the background and a clear blue sky. Large windows accent the upper and lower levels, providing natural light.

Home in Mooresville

Spacious & Quiet, near airport/I-70, sleeps 11