Your Greencastle Vacation

Skip the stress of planning your next epic adventure with a Greencastle vacation package. Whether you're in town for its cuisine, history, art or other highlights, there's a never-ending supply of new experiences to be had. Make your trip to Greencastle even more fun and exciting by including some sightseeing. DePauw University, Putnam County Fairgrounds and Lincoln Park Speedway are some of the big attractions worth exploring. Expedia is here to help you escape your daily routine. Tailor your vacation to Greencastle to suit your travel style, whatever that may be.

Top Greencastle Vacation Deals

Price found within the past 48 hours. Click for updated prices.

Baymont by Wyndham Indianapolis South

CA $1,297

per person

Jul 31 - Aug 4

found 16 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Indianapolis (IND)

7.4/10 Good! (790 reviews)

The front desk staff was so wonderful. I was only there for a night and didn’t do or need a lot. But the gal that checked me in was so sweet. The room was good - giggled at the lack of clock anywhere in the room. Overall would stay again.

Reviewed on Jun 24, 2026

Home2 Suites by Hilton Indianapolis Downtown

Downtown Indianapolis

CA $2,192

per person

Jul 31 - Aug 4

found 16 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Indianapolis (IND)

8.8/10 Excellent! (1,009 reviews)

The breakfast this morning was good. The location of the hotel is great. We went to a basketball game downtown. Staff was friendly Valet service is really well run. They do a great job.

Reviewed on Jun 23, 2026

Motel 6 Indianapolis, IN - Southport

CA $1,625

per person

Jul 31 - Aug 4

found 16 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Indianapolis (IND)

6.6/10 (1,002 reviews)

Not the greatest, but I had no issues.

Reviewed on Jun 9, 2026

Candlewood Suites Indianapolis Northwest by IHG

CA $1,361

per person

Jul 31 - Aug 4

found 16 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Indianapolis (IND)

7.8/10 Good! (389 reviews)

They are in the middle of renovations, so things weren't in the best condition, but the rooms were spacious and had all the amenities that we needed.

Reviewed on Apr 8, 2026

Delta Hotels by Marriott Indianapolis Airport

CA $1,668

per person

Jul 31 - Aug 4

found 16 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Indianapolis (IND)

8.8/10 Excellent! (804 reviews)

I expected more for a delta hotel partnered with Marriott honestly. It was okay, nothing spectacular.

Reviewed on Jun 23, 2026

Ready to book your vacation to Greencastle?

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Greencastle Hotel Deals

Inn at DePauw

2 West Seminary Street Greencastle IN

Fully refundableReserve now, pay when you stay

CA $205

CA $229 total

Jun 28 - Jun 29

includes taxes & fees

9.4/10 Exceptional! (309 reviews)

"We absolutely loved it here! The Inn made our experience visitingDePauw perfect! We would definitely stay here again."

Reviewed on Jun 15, 2026

2-bedroom vacation home minutes away from Greencastle and Depauw campus

Greencastle IN

CA $179

CA $365 total

Jul 9 - Jul 10

includes taxes & fees

9.6/10 Exceptional! (53 reviews)

"We were very pleased with our stay. The peaceful, quiet setting was perfect for a relaxing after a busy day. Our host was awesome. Responded very quickly to any of our questions and so accommodating. We had everything we needed in the kitchen. Very well supplied. A perfect place that meet all our ..."

Reviewed on Jun 5, 2026

A Country Retreat at Airy Knob Farm

Greencastle IN

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See all 187 properties in Greencastle

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.