Holiday houses in Greencastle

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Top-rated holiday rentals in Greencastle

Guests agree: these stays are highly rated for location, cleanliness and more.

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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
4.93 out of 5 average rating, 104 reviews

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.

Guest favourite
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
4.97 out of 5 average rating, 201 reviews

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.

Guest favourite
Guest suite in Mooresville
4.91 out of 5 average rating, 318 reviews

A room with view - great location

This room is a good value. It is close enough to Indianapolis yet peaceful, clean, quiet, and private. We are: 7.1 miles (10 minutes) from Indianapolis international airport. 18 miles (26 minutes) from downtown Indianapolis, 17miles (20 min drive) from Indianapolis convention center and Lucas stadium. 35 miles (52 minutes) from Indiana University in Bloomington. ~3 miles from I-70. If interested in booking please answer our pre booking questions found at the beginning of the house rules.

Top Guest favourite
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
4.91 out of 5 average rating, 146 reviews

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.

Top Guest favourite
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.
Home in Greencastle
4.98 out of 5 average rating, 119 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.

Top Guest favourite
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
4.97 out of 5 average rating, 144 reviews

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. ☺️

Guest favourite
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
4.78 out of 5 average rating, 126 reviews

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.

Top Guest favourite
An open concept living space featuring a kitchen island with seating and a cozy seating area. Large windows provide ample natural light, with views of the surrounding woods. Warm wood flooring enhances the inviting atmosphere, while a door leads to a private area.
Guesthouse in Crawfordsville
5 out of 5 average rating, 149 reviews

Red House Guesthouse

Relaxing guesthouse in peaceful country setting with local deer herd visiting frequently. Close to Shades and Turkey Run State Park and Wabash College. Great location for Covered Bridge Festival, and wedding venues. We live on site with our 2 chocolate Labradors. The guesthouse has a private entrance and private outdoor deck facing the woods. Entire living space is handicapped accessible including large bathroom with walk in shower. Cleaning is in accordance with CDC guidelines.

Top Guest favourite
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
4.98 out of 5 average rating, 243 reviews

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!

Top Guest favourite
The studio features a combined living and sleeping area. A spacious bed is positioned near a wall with wooden cabinetry. A modern kitchen with stainless steel appliances is visible alongside comfortable seating arrangements. Warm wood tones and a well-lit environment create a welcoming atmosphere.
Loft in Greencastle
5 out of 5 average rating, 34 reviews

The Historic Boulders Circa 1910

Within walking distance to DePauw University and Downtown Greencastle in a park like setting on the historic Boulders property. Second floor private studio with an upscale kitchen with full set of appliances, queen size bed with power motion base, private bath, designated office area, WIFI, streaming video, 75 inch flat screen TV, central heat and AC, with access to outdoor patio and dining area with gas grill grill. Off street private parking

Top Guest favourite
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
5 out of 5 average rating, 140 reviews

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.

Top Guest favourite
The living area features a comfortable gray sofa and two armchairs, inviting relaxation. A round coffee table sits at the center, with a soft area rug underneath. The space is filled with natural light, complemented by warm lamps, while shelves in the background house decorative items.
Loft in Mooresville
5 out of 5 average rating, 386 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!

Popular amenities for Greencastle holiday rentals

When is the best time to visit Greencastle?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$294 NZD$329 NZD$331 NZD$317 NZD$348 NZD$331 NZD$268 NZD$296 NZD$329 NZD$334 NZD$357 NZD$286 NZD
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Quick stats about holiday rentals in Greencastle

  • Total holiday rentals

    Explore 40 holiday rentals in Greencastle

  • Nightly prices starting at

    Greencastle holiday rentals start at $87 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,450 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Greencastle holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Greencastle rentals

  • 4.9 Average rating

    Greencastle stays are highly rated by guests—averaging 4.9 out of 5!

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