
Holiday rentals in Greencastle
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Top-rated holiday rentals in Greencastle
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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.

Cozy Cabin Close to University 1
The Red Rabbit Inn is located just 15 mins from the Indiana University campus and just 20 mins from Nashville, IN , this architecturally designed cabin features the works of local artisans. Beautifully landscaped on a secluded, wooded pond, this cabin includes a loft bedroom with KING bed, bath, full kitchen, gas fireplace, satellite TV & Wifi, with your own private deck, outdoor hot tub, fire pit area & gas grill. Cabin sleeps 2 guests. Located near Lake Lemon, in a beautiful serene setting.

Waterfront getaway *cozy & peaceful*fishing*swings
Welcome to your peaceful lakeside getaway! This renovated boho-style cottage offers a quiet and laidback retreat. Featuring an open loft layout, a covered porch, and a large deck overlooking two small serene lakes, this home is designed for relaxation. Enjoy evenings under the Pergola with swings or gather around the hillside firepit for unforgettable nights. Its location also makes it easy for you to get around. You're just: 10 min to I-70 hwy 20 mins to the airport 30 mins to Indy Downtown

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.

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.

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. ☺️

There's No Place Like Dome!
Come enjoy fabulous Bloomington, IN from your own private paradise! The 1400 square-foot renovated dome home boasts panoramic wooded views and sits on 6 acres of a secluded, park-like setting only 17 min. from downtown. The dome sleeps 4 guests with an open, divided, (not fully private) loft with one full bed and one queen bed. There is one full bath, dining for six, island seating and a fully equipped kitchen. It also features a fireplace, laundry facilities and front and back decks.

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.

Treetop Honeymoon Suite at Treetop Retreat
Recently featured in Midwest Living’s “Best Romantic Getaways in Indiana,” The Treetop Suite sits atop one of the highest hills in Brown County and offers sweeping views. This airy loft includes a jetted spa tub, seasonal gas fireplace, full kitchen, and a king bed, an inviting place to relax, recharge, and “nest.” Floor-to-ceiling windows blur the line between indoors and nature, filling the space with light and beautiful hilltop scenery. A truly special, memorable retreat.

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.

Modern Nashville Home in the Woods
Welcome to Plāhaus - a modern home nestled in the woods of Brown County. Plāhaus is a space of solitude and relaxation for anyone wanting to enjoy the beauty of Brown County, without the typical log cabin decor. Enjoy the gorgeous view from the balcony, spend some time around the firepit, and venture into Nashville to check out the unique shops and restaurants. Come for a family getaway, a romantic retreat or simply to clear your mind from the everyday stresses.

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
Other great holiday rentals in Greencastle

Raccoon Lake Retreat

The Carriage House

1860’s Art House

The Trillium House at DePauw - 4/5 BR 3.5 BA

Indulgence at DePauw

The Pond House at Deer Creek Farms/ Greencastle

Creekside Cottage

The Studio - Moonstone on Walnut
When is the best time to visit Greencastle?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $216 SGD | $241 SGD | $243 SGD | $233 SGD | $255 SGD | $243 SGD | $210 SGD | $224 SGD | $241 SGD | $239 SGD | $238 SGD | $212 SGD |
| Avg. temp | -2°C | 0°C | 6°C | 12°C | 18°C | 23°C | 24°C | 24°C | 20°C | 13°C | 6°C | 1°C |
Frequently Asked Questions
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.
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 apartment rentals in Greencastle have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Greencastle. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Greencastle have a kitchen?
Absolutely! We offer over 30 house rentals with a kitchen in Greencastle. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Greencastle have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Greencastle. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Greencastle have free parking?
Absolutely! We offer over 10 apartment rentals with free parking in Greencastle. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Greencastle?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with wifi, over 10 homes with air conditioning, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
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 $64 SGD 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 & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
50 of Greencastle holiday rentals include wifi 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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- Lucas Oil Stadium
- Indianapolis Motor Speedway
- Indiana Convention Center
- Eagle Creek Park
- Indianapolis Zoo
- The Golf Club at Eagle Pointe
- Brown County State Park
- Gainbridge Fieldhouse
- Brickyard Crossing
- Indiana State Fairgrounds & Event Center
- McCormick's Creek State Park
- Oliver Winery
- Childrens Museum
- Grand Park Sports Campus
- Indianapolis Museum of Art
- Butler University
- Yellowwood State Forest
- White River State Park
- Garfield Park
- Indiana State Museum
- IUPUI Campus Center
- Fort Harrison State Park
- Indianapolis Canal Walk
- Monroe Lake




