Book Holiday Homes in Greencastle

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Featured Holiday Homes in Greencastle

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

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

2 out of 5
Rockville
With a stay at this vacation home in Rockville, you'll be within a 5-minute drive of 1883 Train Depot and Billie Creek Village.
Cute, pet-friendly home in quiet neighborhood. Close to state parks & downtown.
A Cozy, relaxing hideaway! 1/2 a mile from Billie Creek Covered Bridge.

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

Rockville
The price is AU$496 per night from 16 Apr to 17 Apr
AU$496
includes taxes & fees
16 Apr - 17 Apr
A stay at this vacation home places you in the heart of Rockville, within a 5-minute drive of Billie Creek Village and 1883 Train Depot.
A Cozy, relaxing hideaway! 1/2 a mile from Billie Creek Covered Bridge.
Country Hideaway but close to town

Country Hideaway but close to town

Greencastle
The price is AU$532 per night from 16 May to 17 May
AU$532
includes taxes & fees
16 May - 17 May
Located in Greencastle, this vacation home is in a rural location, a 4-minute drive from Deer Creek Fish and Wildlife Area and 8 minutes from Scott Hamilton ...
Country Hideaway but close to town
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4 Mi to Dtwn: Danville Home w/ Patio & Yard

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

Danville
Located in Danville, this vacation home is within a 15-minute drive of Splash Island and Regal Shiloh Crossing.
4 Mi to Dtwn: Danville Home w/ Patio & Yard
Millstone retreat

Millstone retreat

Coatesville
The price is AU$736 per night from 16 May to 17 May
AU$736
includes taxes & fees
16 May - 17 May
With a stay at this vacation home in Coatesville, you'll be 29.1 mi (46.9 km) from Indianapolis Motor Speedway and 31.3 mi (50.4 km) from Indiana Convention ...
Millstone retreat
Artesian Spring house!  2 Bed, 2 bath, equipped kitchen and laundry.

Artesian Spring house! 2 Bed, 2 bath, equipped kitchen and laundry.

Spencer
The price is AU$175 per night from 18 Apr to 19 Apr
AU$175
includes taxes & fees
18 Apr - 19 Apr
Located in Spencer, this vacation home is a 3-minute drive from McCormick's Creek State Park and 6 minutes from Owen County Heritage and Culture Center.
Artesian Spring house! 2 Bed, 2 bath, equipped kitchen and laundry.
Bridge-view at Cataract Falls Lodge

Bridge-view at Cataract Falls Lodge

Spencer
Located in Spencer, this vacation home is in a rural location, within a 15-minute drive of Cataract Falls and Duck Island.
Bridge-view at Cataract Falls Lodge
1840 Homestead

1840 Homestead

Jamestown
The price is AU$450 per night from 23 Apr to 24 Apr
AU$450
includes taxes & fees
23 Apr - 24 Apr
With a stay at this vacation home in Jamestown, you'll be 25.4 mi (40.9 km) from Indianapolis Motor Speedway and 31.3 mi (50.3 km) from Indiana Convention ...
1840 Homestead
Lake house w/seasonal pool and boat storage.

Lake house w/seasonal pool and boat storage.

Poland
Located in Poland, this vacation home is on a lake, a 1-minute drive from Ernie Pyle Island and 6 minutes from Lieber State Park.
Lake house w/seasonal pool and boat storage.
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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.

Greencastle Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Greencastle vacation homes are the perfect way for you to wing it.

Holiday houses in Greencastle let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Greencastle in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Greencastle adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Greencastle with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Greencastle vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Greencastle Holiday Homes essential information

Accommodation
54 Holiday Homes
Lowest Price
AU$175
Highest Price
AU$736
Popular accommodation
Cute, pet-friendly home in quiet neighborhood. Close to state parks & downtown., A Cozy, relaxing hideaway! 1/2 a mile from Billie Creek Covered Bridge., Country Hideaway but close to town, 4 Mi to Dtwn: Danville Home w/ Patio & Yard, Millstone retreat, Artesian Spring house! 2 Bed, 2 bath, equipped kitchen and laundry., Bridge-view at Cataract Falls Lodge, 1840 Homestead , Lake house w/seasonal pool and boat storage.

Top trending hotels in Greencastle

Inn at DePauw

Inn at DePauw

3.5 out of 5
2 West Seminary Street, Greencastle, IN
Fully refundableReserve now, pay when you stay
The price is AU$263 per night from 20 Apr to 21 Apr
AU$263
includes taxes & fees
20 Apr - 21 Apr
With a stay at Inn at DePauw in Greencastle, you'll be within a 5-minute walk of DePauw University and Roy O West Library.
Inn at DePauw
Country Hideaway but close to town

Country Hideaway but close to town

Greencastle
The price is AU$532 per night from 16 May to 17 May
AU$532
includes taxes & fees
16 May - 17 May
Located in Greencastle, this vacation home is in a rural location, a 4-minute drive from Deer Creek Fish and Wildlife Area and 8 minutes from Scott Hamilton ...
Country Hideaway but close to town
The Trillium House at DePauw - 4/5 BR 3.5 BA

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

Greencastle
The price is AU$614 per night from 29 Apr to 30 Apr
AU$614
includes taxes & fees
29 Apr - 30 Apr
With a stay at this vacation home in Greencastle, you'll be a 1-minute walk from DePauw University and 8 minutes by foot from Judson and Joyce Green Center for ...
The Trillium House at DePauw - 4/5 BR 3.5 BA
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Charming 3-bedroom farmhouse in marvelous Greencastle near DePauw University

Charming 3-bedroom farmhouse in marvelous Greencastle near DePauw University

2 out of 5
Greencastle
With a stay at this farm stay in Greencastle, you'll be a 4-minute walk from DePauw University and 6 minutes by foot from Mary Rogers Field Park.
Charming 3-bedroom farmhouse in marvelous Greencastle near DePauw University
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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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^Subject to availability and chosen travel dates.