Greencastle Vacations

Book a Hotel + Flight together to unlock savings

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  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place

Find the Best Greencastle Vacation Packages

Greencastle Hotel Deals

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 SARĀ 540 per night from Jul 19 to Jul 20
SARĀ 540
SARĀ 605 total
19 Jul - 20 Jul
includes taxes & fees
9.4/10 Exceptional! (311 reviews)
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Reviewed on 25 June 2026

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

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

Greencastle IN
The price is SARĀ 473 per night from Jul 19 to Jul 20
SARĀ 473
SARĀ 967 total
19 Jul - 20 Jul
includes taxes & fees
9.6/10 Exceptional! (55 reviews)
"Everything was tidy. The Wifi wasn't working, She came over to troubleshoot. worked with support to no success; However, By the next morning the internet was back and then we commence watching FIFA and playing on the laptops we brought. I love the place. Loved the Hot Tub, the "indoor" Porch was ..."

Reviewed on 15 July 2026

2-bedroom vacation home minutes away from Greencastle and Depauw campus
Days Inn by Wyndham Cloverdale Greencastle

Days Inn by Wyndham Cloverdale Greencastle

2 out of 5
1031 N. Main St. Cloverdale IN
Fully refundableReserve now, pay when you stay
The price is SARĀ 281 per night from Jul 20 to Jul 21
SARĀ 281
SARĀ 315 total
20 Jul - 21 Jul
includes taxes & fees
Days Inn by Wyndham Cloverdale Greencastle
See all 186 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.

Stay near popular Greencastle attractions

Skeins of yarn in various colors hanging in a store.
Photo by Sig
Open Photo by Sig

Putnam County Fairgrounds

8.2/10 (31 reviews)
The Putnam County Fairgrounds hosts Indiana's cherished agricultural showcase featuring livestock exhibitions, community events, local culture, and traditional competitions each July, complete with regional food vendors.
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Frequently asked questions

How much does a Greencastle vacation package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a vacation to Greencastle costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Greencastle?
You can usually find reduced prices and greater availability in January, March and August. Browse our cheap Greencastle vacation packages and you could land some great off-season deals.
How to find the best Greencastle package deals?
Finding a cheap Greencastle package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, add a few filters and browse what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Greencastle package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Greencastle vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and accommodations separately. Better still, you can tailor your Greencastle escape to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Greencastle?
If you're considering a spur-of-the-moment Greencastle trip, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Greencastle?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to visit Greencastle.
  2. Set your budget: Consider costs like food, flights and transportation when working out how much to put aside for your trip to Greencastle. Then, select a hotel that matches your budget, whether that's an affordable option or a lavish getaway.
  3. Set the duration of your trip: Start by listing all the sights and activities you want to experience in Greencastle. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a customized Greencastle vacation package.