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 quaint one-room cabin nestled in a lush green forest, featuring a welcoming front porch with two blue chairs and a small table. The wooden structure is complemented by natural surroundings and has steps leading up to the entrance, creating a rustic yet inviting appearance.
Cabin in Bainbridge
4.93 out of 5 average rating, 105 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, 204 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.

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, 149 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, 126 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, 153 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
Home in Greencastle
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.

Guest favourite
Apartment in Mooresville
4.83 out of 5 average rating, 218 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.

Guest favourite
The cabin's open kitchen is highlighted by wood-paneled walls, showcasing a spacious countertop and essential appliances. Large windows invite natural light and offer views of the surrounding woods. A dining area with wooden chairs and a table complements the rustic atmosphere.
Cabin in Martinsville
4.91 out of 5 average rating, 502 reviews

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!.

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, 134 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.

Guest favourite
A view of the dining area is presented, featuring a wooden table set in the center beneath a pendant light. The floor is adorned with a patterned rug, surrounded by windows that allow for natural light. A sideboard can be seen against the wall.
Home in Farmersburg
4.9 out of 5 average rating, 115 reviews

The Main Street Retreat-NO CLEANING FEES

Enjoy your time to simply get away or as a must need sleep over due to travel or work. Only 14 miles south of I70. A Dollar General Store, Subway and Gas Station are nearby. Ten minute drive south to Sullivan for Walmart, restaurants, and grocery stores. Fifteen minute drive north to Terre Haute for all the city attractions. County and State Parks are near by as well. Located in a great neighborhood on main street with privacy. Maximum of only four adults allowed per reservation.

Top Guest favourite
A spacious great room is featured, equipped with a comfortable black sofa and a wooden coffee table. A kitchenette is visible with modern appliances, and a curved bar area with stools provides additional seating. Recessed lighting and a ceiling fan illuminate the area.
Villa in Spencer
4.94 out of 5 average rating, 110 reviews

Bridge-View Suite at Cataract Falls

Welcome to Cataract Falls Lodge at the entrance to the Cataract Falls State Recreation Area. A one minute walk from the lodge and you will be standing on the overlook of the most spectacular waterfall in the Midwest. The lodge has three private suits that can be rented individually or combination thereof. This unit, Bridge-View, sleeps 4 offering one bedroom, a great room with attached kitchenette, full bathroom and personal outdoor space overlooking the entrance to the park.

Top Guest favourite
Home in Brazil
4.93 out of 5 average rating, 363 reviews

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.

Popular amenities for Greencastle holiday rentals

When is the best time to visit Greencastle?

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Avg. price$237 AUD$265 AUD$267 AUD$256 AUD$281 AUD$267 AUD$230 AUD$246 AUD$265 AUD$263 AUD$261 AUD$233 AUD
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Frequently Asked Questions

  • Do house rentals in Greencastle have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Greencastle. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Greencastle?

    Greencastle has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Greencastle?

    Experience the best of Greencastle with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Greencastle have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Greencastle. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Greencastle have a kitchen?

    Absolutely! We offer over 20 house rentals with a kitchen in Greencastle. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Greencastle?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with air conditioning, over 20 homes with free parking, over 20 homes with wifi, over 20 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there house rentals with a dedicated workspace in Greencastle?

    Yes! Work meets play with ease at over 10 house rentals in Greencastle featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Greencastle have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Greencastle. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Greencastle

  • Total holiday rentals

    Explore 50 holiday rentals in Greencastle

  • Nightly prices starting at

    Greencastle holiday rentals start at $70 AUD per night before taxes and fees

  • Verified guest reviews

    Over 2,660 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Greencastle holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi 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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