Vacation rentals in Greencastle

4.93 out of 5 average rating, 105 reviews

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

Covered Bridge Cabin (on Big Walnut Creek)

Retreat and renew in this charming one-room cabin 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 picture window, inflatable single mattress, small TV, writer's desk, AC, fans and baseboard heat, kitchenette, toilet, sink, outdoor shower (before first frost), small porch, grill, and a fire pit. (No wifi in cabin.) Simple and beautiful.

4.97 out of 5 average rating, 202 reviews

The exterior of Namaste Lofts is shown, highlighting the red brick façade and large windows with green awnings. Nearby sidewalk seating is visible, along with surrounding storefronts, creating a vibrant downtown atmosphere.

Loft in Greencastle

NAMASTE Lofts - Downtown Greencastle!

Looking for peace and serenity in the heart of downtown Greencastle, welcome to Namaste Lofts! We provide 2 distinctively designed lofts that exude a sense of calmnessin the bustling downtown. Each unit reflects the architectural features from the 1800’s, but the eclectic design with a mix of urban & modern furnishings makes the lofts a one of a kind place to stay. Located on the north side of Greencastle’s downtown square, you are walking distance to all entertainment, and DePauw University.

4.91 out of 5 average rating, 149 reviews

A modern kitchen space is featured, showcasing an island with bar stool seating. Nearby, a decorative wall art piece adds color. A glass bookshelf displays various items, complemented by a dining table against the wall. Warm light enhances the inviting atmosphere.

Loft in Greencastle

Courthouse Square Loft

At the intersection of DePauw University and historic downtown Greencastle! Recently renovated, our spacious and modern Loft is located above Scoops Ice Cream Shop and overlooks Greencastle’s Courthouse Square Historic District. You’ll be just steps away from many fantastic restaurants, boutiques, and charming shops. Come and enjoy scenic Putnam County all throughout the year! We are a short walk from the DePauw campus and close to many covered bridges. Turkey Run State Park is a short drive.

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, 124 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.

Guesthouse in Crawfordsville

The living area is furnished with a comfortable brown pull-out sofa and two chairs. A wooden coffee table sits in front, accompanied by a decorative area rug. Natural light enters through a window, with light curtains enhancing the cozy feel of the space.

4.96 out of 5 average rating, 618 reviews

Mimi's Country Cottage

Quaint, quiet and cozy cottage set in a tranquil park like setting with all the amenities of home. Ten minutes to Shades State Park and twenty minutes to Turkey Run State Park. A great place to stay for the Covered Bridge Festival. 15 minutes to Wabash College, 25 minutes to DePauw University, 45 minutes to Purdue. We live on site and our back door is approximately 600 ft. from from the Airbnb. At this time we do not allow pets. We clean the cottage in accordance with CDC guidelines.

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.

4.93 out of 5 average rating, 106 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.

4.91 out of 5 average rating, 499 reviews

The living area features wooden walls and ceilings, complemented by large windows that allow natural light to illuminate the space. Two seating areas include a brown sofa adorned with cushions and a rust-colored recliner, alongside a coffee table. A dining area can be seen in the background.

Cabin in Martinsville

Grandpa's Cabin at Heidenreich Hollow

Grandpa’s Cabin at Heidenreich Hollow offers exclusive lodging on our hilly 5 acre wooded property. We offer a peaceful getaway from life while being right in the middle of both Indianapolis and Bloomington! Our quiet rustic cabin has a loft bedroom with stair access that includes a King size bed, 2 twin beds and an air mattress. We have a spacious bathroom and a fully equipped kitchen to help you feel at home. Search YouTube for Grandpas Cabin at Heidenreich Hollow for a video!.

4.78 out of 5 average rating, 134 reviews

The rustic barn is set against a vibrant sunrise sky, showcasing a mix of pink and orange hues. Lush green grass surrounds the barn, with farm equipment visible nearby. Trees and open fields fill the background, reflecting the charm of the rural landscape.

Barn in Rockville

The 1938 Barn

The 1938 Barn is located in the ❤ of Covered Bridge Country in Parke County. You will love the rustic charm of this converted hay barn built in 1938. Come relax by the camp fire or explore our many Covered Bridges and local State Parks. The farm also hosts Henry's Market, a market garden providing fresh meat and vegetables which makes summertime an excellent time to visit! Please note: There is NO WI-FI, NO CABLE. We have a selection of DVDs. Limited cell service, AT&T works best.

Superhost

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

4.94 out of 5 average rating, 224 reviews

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.

4.98 out of 5 average rating, 250 reviews

A single-story cabin is framed by lush greenery, showcasing natural wood siding and a welcoming front porch. The porch features seating arrangements and decorative elements, while the pathway leads to a gravel driveway, enhancing the serene ambiance of the surrounding woods.

Cabin in Carbon

Parke County Dream Cabin

Come experience the serenity of country living and get away from the daily grind of everyday life. Come fish in our five-acre lake (catch & release only), paddle-boat, kayak, or stroll through the woods. A covered porch and seating lakeside for relaxing. Located close to Mansfield and Bridgeton, 30 minutes from Turkey Run State Park, and only 30 minutes toTerre Haute or Greencastle. Come explore everything Parke County has to offer! KIDS WELCOME!

5 out of 5 average rating, 142 reviews

A cozy living area features a dark gray sofa adorned with yellow and patterned throw pillows. A television is mounted on the wall, with a wooden entertainment center below. A lamp stands beside the couch, and a potted plant is positioned near a window.

Loft in Spencer

Carriage House 1 bedroom loft suite w/ fireplace.

Keep it simple at this peaceful and centrally-located loft. Carriage House Guest Suite is located in a quiet neighborhood just five blocks from the courthouse square. Spencer's historic downtown offers the restored Tivoli theater, restaurants, art galleries & shops. Two miles from beautiful McCormick's Creek State Park and 3 miles to Owen Valley Winery. A convenient 20 miles to downtown Bloomington & Indiana University.

Popular amenities for Greencastle vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Greencastle

5 out of 5 average rating, 20 reviews

A spacious living room features a rounded gray sectional sofa facing a flat-screen TV on a wooden stand. Natural light enters through a window, with a view of greenery. A wall with rustic wood paneling adds texture, complemented by a clock and plants.

Guesthouse in Rockville

Raccoon Lake Retreat

Superhost

A charming green two-story structure is viewed from the street, featuring a covered porch and decorative gables. A large tree is positioned in front, providing shade. A parking area with a vehicle is visible in the foreground, along with a walkway leading toward the entrance.

Apartment in Greencastle

4.8 out of 5 average rating, 10 reviews

The Carriage House

The exterior of a charming house is depicted, featuring light-colored siding and multiple gabled roofs. A landscaped path lined with flower pots leads to the entrance, surrounded by lush green grass and vibrant shrubs, creating a welcoming appearance in the daylight.

4.96 out of 5 average rating, 50 reviews

Major Dunbar Home

4.99 out of 5 average rating, 75 reviews

A comfortable living area is highlighted by hardwood floors and wooden beam ceilings. A cozy sofa is positioned opposite a media console, which houses a television. Natural light enters through a window, complementing the soft tones of the furnishings and decor.

Home in Danville

The Cozy Cottage II

A two-story brick home is visible, featuring a symmetrical façade with a centered entrance. Two white chairs are positioned on the front porch, and well-maintained shrubbery surrounds the entryway. A manicured lawn adds to the home's appeal, complemented by small garden beds with diverse foliage.

4.98 out of 5 average rating, 61 reviews

Greencastle Retreat:Hot Tub Haven & Fireside Charm

5 out of 5 average rating, 7 reviews

The living area features a comfortable gray sofa, accent chair, and modern desk under a ceiling fan. A smart TV sits on a stylish stand next to an electric fireplace. Large windows provide natural light and views of the peaceful street outside.

Apartment in Plainfield

Marvelous 1 Bedroom Main Street Retreat

4.8 out of 5 average rating, 35 reviews

The front porch features a set of wicker chairs and a black chair, inviting relaxation. Steps lead to a well-maintained pathway, bordered by greenery, while the house's white exterior is complemented by a gray roof. A large yard is visible beyond the porch.

Home in Bridgeton

Grandma Mitchell’s House

The exterior of the home is captured from above, featuring a red metal roof and a surrounding expansive lawn. Towering trees provide a natural boundary, and gravel pathways border the manicured yard, enhancing the serene setting.