Vacation rentals in Greencastle

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Top-rated vacation rentals in Greencastle

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

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Guest favorite
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, 202 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 favorite
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 favorite
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, 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.

Top guest favorite
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, 149 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 favorite
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.
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.

Top guest favorite
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, 113 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.

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, 223 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.

Guest favorite
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.
Home in Greencastle
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.

Top guest favorite
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, 249 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 favorite
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, 142 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 favorite
Loft in Mooresville
5 out of 5 average rating, 394 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!

Top guest favorite
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.
Home in Greencastle
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.

Popular amenities for Greencastle vacation rentals

When is the best time to visit Greencastle?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR2,852 ZARR3,189 ZARR3,206 ZARR3,071 ZARR3,375 ZARR3,206 ZARR2,767 ZARR2,953 ZARR3,189 ZARR3,240 ZARR3,459 ZARR2,767 ZAR
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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 wifi, over 20 homes with a kitchen, over 20 homes with free parking, over 20 homes with air conditioning, 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 vacation rentals in Greencastle

  • Total vacation rentals

    Explore 40 vacation rentals in Greencastle

  • Nightly prices starting at

    Greencastle vacation rentals start at R844 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 2,450 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Greencastle vacation 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!

  1. Airbnb
  2. United States
  3. Indiana
  4. Putnam County
  5. Greencastle