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Holiday Homes in Greencastle

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Featured Holiday Homes in Greencastle

Spacious 4-bedroom house in Serene Country Setting - sleeps up to 11

9.4 out of 10, Exceptional, (3)
"This property was perfect for our large group. The drscription was accurate, the propery was clean, easy to find, and the host was responsive. "
The price is AU$694
includes taxes & fees
2 Dec - 3 Dec
Spacious 4-bedroom house in Serene Country Setting - sleeps up to 11

Cute, pet-friendly home in quiet neighborhood. Close to state parks & downtown.

2.0 star property
9.8 out of 10, Exceptional, (10)
"Very clean and comfortable. Property owner communicated well, we will be back."
Cute, pet-friendly home in quiet neighborhood. Close to state parks & downtown.

Quaint century-old home just minutes from Turkey Run & Shades State Park

9.2 out of 10, Wonderful, (21)
"This is a cozy little home in a small town within a nine minute drive of Turkey Run State park, and nine miles from Shades State Park and Rockville ( which has some quaint specialty and antique stores). The host has it well stocked (above and beyond what most VRBO hosts do) with snacks, condiments, and a coffe bar! Stacie was very responsive to all my texts and questions throughout our stay. It suited my sister and I well for our stay."
Quaint century-old home just minutes from Turkey Run & Shades State Park

This home is located in beautiful Parke County, a rustic and charming setting.

10.0 out of 10, Exceptional, (78)
"Thank you for the beautiful stay!! "
This home is located in beautiful Parke County, a rustic and charming setting.

Creekside cottage with hot tub and fishing

10.0 out of 10, Exceptional, (7)
"Stayed here so we woud be close to a gamily wedding. Very nice and vlean highly recommend."
Creekside cottage with hot tub and fishing

The Rosedale House

2.0 star property
10.0 out of 10, Exceptional, (2)
"Brian was great at quickly responding to questions. House just as advertised. Very clean. Hot tub and fire pit with wood available but we didn’t use. (May want to add night stand lamps in bedrooms and reading light in living room, as there is mostly just ceiling lights) very close to Bridgeton, primary location of Covered Bridge Festival. "
The price is AU$457
includes taxes & fees
3 Dec - 4 Dec
The Rosedale House

4 Mi to Dtwn: Danville Home w/ Patio & Yard

4 Mi to Dtwn: Danville Home w/ Patio & Yard

A Cozy, relaxing hideaway! 1/2 a mile from Billie Creek Covered Bridge.

10.0 out of 10, Exceptional, (50)
"We really enjoyed out stay. Place is immaculate and comfortable. Loved the covered outside deck and so did our Scottie dog! Wish we could have stayed longer. Will definitely look forward to staying there again. Thank you Bob and Joanne!"
The price is AU$380
includes taxes & fees
2 Dec - 3 Dec
A Cozy, relaxing hideaway! 1/2 a mile from Billie Creek Covered Bridge.

The Getaway House with Hot Tub and Pool. Pet Friendly

9.4 out of 10, Exceptional, (9)
"We had a great stay. Nice quiet location , all the amenities you would need in a stay no matter what time of year. Tony and Lisa were great hosts . .W W"
The Getaway House with Hot Tub and Pool. Pet Friendly

1840 Homestead

10.0 out of 10, Exceptional, (37)
"Overall a 10/10.We loved this little homestead house.everything was clean,neat,and very homie.The big surprise for us though was only a few steps away outside.We was not expecting this wonderfull warm ,soothing,relaxer.It really made our5 hour drive from southern Michigan worth the arrival,to ease our anxiety from the long drive.A perfect end to a long day.We recommend this property.And will love to stay again more than one night next time."
The price is AU$426
includes taxes & fees
9 Dec - 10 Dec
1840 Homestead

Home in Brazil

10.0 out of 10, Exceptional, (8)
"Clean and comfortable, great communication with owner "
The price is AU$182
includes taxes & fees
8 Dec - 9 Dec
Home in Brazil

Bridge-view Family Suite

10.0 out of 10, Exceptional, (2)
"Beautiful property and beautiful accommodations! "
Bridge-view Family Suite

Quiet retreat nestled in the woods.

The price is AU$692
includes taxes & fees
1 Dec - 2 Dec
Quiet retreat nestled in the woods.

Sugar Creek Escape at Turkey Run

10.0 out of 10, Exceptional, (62)
"Better than a 5 star hotel!"
Sugar Creek Escape at Turkey Run

Lake house w/seasonal pool and boat storage.

9.8 out of 10, Exceptional, (24)
"The house was clean, comfortable, and charming!"
Lake house w/seasonal pool and boat storage.

Events Welcome! Exclusive 65-Acre Gated Estate w/ Indoor Pool & Private Lake

10.0 out of 10, Exceptional, (5)
"Beautiful home but the property is where it is at. Absolutely gorgeous. We really appreciate the extra towels and comfy beds. Kids had a blast in the bunk room with some AM cartoons while the adults shook over hangovers. Pool super cool. Only drawback is there were some lights we did not know how to turn on. Didn't ask though, property manager was great keeping us informed and answering questions. thinking about coming back next year!"
The price is AU$1,745
includes taxes & fees
2 Dec - 3 Dec
Events Welcome! Exclusive 65-Acre Gated Estate w/ Indoor Pool & Private Lake

Amazing Spacious Luxury Home - Sleeps Up To 16!

8.8 out of 10, Excellent, (12)
"Stayed here"
Amazing Spacious Luxury Home - Sleeps Up To 16!

Millstone retreat

9.8 out of 10, Exceptional, (75)
"This was a fantastic place to stay. We were in town for a concert and there was plenty of room for 3 adults and a teen. This property is beautiful. We loved feeding the ducks!! It’s very quiet there also. The inside of the home is dated but didn’t bother us a bit!! It was very cozy and welcoming. "
The price is AU$704
includes taxes & fees
1 Dec - 2 Dec
Millstone retreat

Perfect spot! Martinsville's Beautiful Leaves, IU Football to Indy nightlife!

10.0 out of 10, Exceptional, (4)
"Nice little place for our short stay to go to an IU game. Slept 4 adults with no issues."
The price is AU$530
includes taxes & fees
4 Dec - 5 Dec
Perfect spot! Martinsville's Beautiful Leaves, IU Football to Indy nightlife!

Huge Main Bedroom with En-suite Close proximity to Rose Hulman

10.0 out of 10, Exceptional, (11)
"Great for our family! Everyone enjoyed the property"
Huge Main Bedroom with En-suite Close proximity to Rose Hulman
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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Other property types in Greencastle

Charming Greencastle Home < 1 Mi to DePauw!

10.0 out of 10, Exceptional, (11)
"Property was clean and nice, just wish it had a dining table, but would definitely stay there again!"
Charming Greencastle Home < 1 Mi to DePauw!

The Major Dunbar Home

10.0 out of 10, Exceptional, (2)
"I booked this property for the groomsman party of my friend’s wedding and it was great. There was plenty of space for us all to be comfortable and get ready for the wedding. The wedding venue, Owl Ridge, was only 5 minutes away. A coffee shop was also in walking distance. Communication with the host was very efficient and simple. It was a great weekend"
The Major Dunbar Home

Charming Greencastle Home < 1 Mi to Depauw!

3.0 star property
Charming Greencastle Home < 1 Mi to Depauw!
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.