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Greencastle Holiday Rentals

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Holiday Rentals in Greencastle

Holiday Home in Greencastle

9.6 out of 10, Exceptional, (40)
"Great place to stay and close to Greencastle! Fully stocked."
United States
Michael W.
The price is AU$392
includes taxes & fees
11 Dec - 12 Dec
2-bedroom vacation home minutes away from Greencastle and Depauw campus

Holiday Home in Greencastle

Modern 4BR Home on Golf Course + Sauna Close to Campus, Dining & Entertainment

Cottage in Greencastle

3.0 star property
Charming Greencastle Home < 1 Mi to Depauw!

Apartment in Greencastle

8.0 out of 10, Very good, (1)
"Towel bar feel off wall, had trouble with the TV. Host accommodating with pet and early checkin. "
United States
Amber O.
The price is AU$578
includes taxes & fees
7 Dec - 8 Dec
Charming 1BR Retreat Near DePauw University & Downtown Greencastle!

Holiday Home in Greencastle

10.0 out of 10, Exceptional, (7)
"Beautiful home, great location. Accommodating hosts. Five senior woman from 4 statesenjoyed a wonderful time of reminiscing their time spent together in high school. "
United States
Anonymous traveller
The Major Dunbar Home

Holiday Home in Greencastle

10.0 out of 10, Exceptional, (6)
"We couldn't ask for a better place to stay. Trillium House was absolutely perfect, even better than the pictures on line. The owners thought of every detail to make our stay as comfortable as possible and the house was spotless. The location was perfect for anyone visiting DePauw and easily walkable to town. We'll definitely be back!"
United States
molly c.
The Trillium House at DePauw - 4/5 BR 3.5 BA

Holiday Home in Terre Haute

10.0 out of 10, Exceptional, (4)
"It was perfect for our gathering!!When we needed help the response was perfect. Great job Kyle and team"
United States
Phillip W.
Barndominium! Pool, HotTub, Slide, Mini B-Ball Court/Nerf Arena, Theater, 2 Bars

Cabin in Spencer

9.8 out of 10, Exceptional, (6)
"Cute, clean little cabin near Mccormicks Creek State Park"
United States
Gina C.
The price is AU$130
includes taxes & fees
14 Dec - 15 Dec
Celtic Glen Farm Stay - Mini Log Cabin

Holiday Home in Coatesville

9.8 out of 10, Exceptional, (94)
"Millstone is a wonderful house. The pics on the site do it justice. We went to an event in Indianapolis, and we were close enough to make the drive easy while feeling far enough away to enjoy the peace and quiet.The kids loved the boats on the pond. Feed the ducks!"
United States
Gavin R.
The price is AU$621
includes taxes & fees
19 Dec - 20 Dec
Millstone retreat

Holiday Home in Rockville

2.0 star property
10.0 out of 10, Exceptional, (53)
"Nice location to everything "
United States
Brad B.
Cute, pet-friendly home in quiet neighborhood. Close to state parks & downtown.

Holiday Home in Terre Haute

10.0 out of 10, Exceptional, (1)
"Gorgeous house for our XC weekend in IN! The kitchen was extremely well stocked and perfect for cooking a full team dinner. The range was a little tricky at first, but once we found the burner diagram on the back of the top left cabinet, it was smooth sailing.All of the rooms were very clean, and the beds were comfortable. My crew especially loved the indoor pool, it was such a fun bonus!The WiFi was quite slow and wouldn’t load any streaming services for our movie night, though we were able to...
United States
Cana M.
The price is AU$2,257
includes taxes & fees
2 Jan - 3 Jan 2026
Deer Run Lodge/Indoor Pool/Hot Tub/Sauna

Holiday Home in Coatesville

9.6 out of 10, Exceptional, (13)
"The stay was wonderful and convenient to the Hendricks County Fairgrounds."
United States
Alyson M.
The price is AU$798
includes taxes & fees
8 Dec - 9 Dec
Life-Giving, Quiet retreat only 25 min west of Indpls. Peace, Pace, & Gratitude

Holiday Home in Marshall

10.0 out of 10, Exceptional, (7)
"This property was amazing!"
United States
Kate L.
Luxury Amish Built Barn Home at Turkey Run

Cabin in Martinsville

8.6 out of 10, Excellent, (19)
"Great stay!"
United States
Cameron S.
The price is AU$435
includes taxes & fees
8 Dec - 9 Dec
Hilltop Cabin, Lake, Hot tub

Apartment in Rosedale

10.0 out of 10, Exceptional, (184)
"We came to Rosedale to visit relatives, so not exactly a weekend getaway, but it was so nice to have this place all to ourselves. "
United States
Angel B.
The price is AU$343
includes taxes & fees
15 Dec - 16 Dec
Getaway in the country/Beautiful Parke County/Large hot tub and much more!

Holiday Home in Rockville

10.0 out of 10, Exceptional, (99)
"Loved the house, so cute. Conveniently located to Turkey Run State Park"
United States
Tonya F.
This home is located in beautiful Parke County, a rustic and charming setting.

Apartment in Waveland

9.8 out of 10, Exceptional, (49)
"Fantastic unique place. We were very comfortable and had fun exploring the games in the common area. "
United States
Tamara
Quaint Apartment - 10 Min from Turkey Run and Shades, Pet Friendly

Holiday Home in Brazil

10.0 out of 10, Exceptional, (18)
"Absolutely percent the nicest place to stay!! All new and very clean, property was gorgeous!! Would stay here again and again!!!"
United States
Jessica W.
Creekside cottage with hot tub and fishing

Cabin in Crawfordsville

10.0 out of 10, Exceptional, (2)
"Host was very friendly and accessible! Wonderful place to stay!"
United States
Holly R.
Cozy lakefront cabin with kayaks

Cabin in Bloomingdale

9.8 out of 10, Exceptional, (38)
"Beautiful view from cabin. Host communicated well."
United States
Julie P.
Treetops Cabin in the Woods!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Greencastle Hotel Reviews

Find out more about Greencastle

Everything you need to know about Greencastle holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Greencastle holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Greencastle holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Greencastle holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Greencastle. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Greencastle holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Greencastle holiday rentals we have selected for you start as low as AU$130 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Greencastle rentals

At Expedia, we put the best Greencastle holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Greencastle rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Greencastle holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Greencastle. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Greencastle?

Yes, there are holiday rentals in Greencastle close to Putnam County Fairgrounds, or you can select a more secluded option if you're looking for a relaxing stay. Greencastle is known for its university setting and restaurants. Make sure you have time to check out the festivals while you're in the area.

What are some of the best holiday rentals that Greencastle has to offer?

2-bedroom vacation home minutes away from Greencastle and Depauw campus: This highly rated holiday home rental in Greencastle is located in a rural location, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with 1 hot tub and a selection of books.

How many holiday rentals are there in Greencastle?

With 11 Expedia holiday rentals, you're guaranteed to find just the right place for your Greencastle stay.

What can I see and do in Greencastle?

Cultural attractions include Robe Ann Park Ampitheater and Judson and Joyce Green Center for the Performing Arts, whereas DePauw Nature Park and Old Quarry Lake are a couple of picturesque spots to enjoy the outdoors. While here, Putnam County Fairgrounds and Lincoln Park Speedway are other places worth a visit.

What are holiday rentals like in Greencastle?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Greencastle. Holiday rentals offer amenities like laundry facilities and kitchens so you'll have everything you need. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.