Greencastle Holidays

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    Save up to S$1,300 when you book a flight and hotel together*

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Top 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 S$175 per night from 16 Nov to 17 Nov
S$175
16 Nov - 17 Nov
includes taxes & fees
Inn at DePauw
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 S$106 per night from 15 Nov to 16 Nov
S$106
15 Nov - 16 Nov
includes taxes & fees
Days Inn by Wyndham Cloverdale Greencastle
Best Western Plus Covered Bridge Inn

Best Western Plus Covered Bridge Inn

2.5 out of 5
3882 N State Road 59 Brazil IN
Fully refundableReserve now, pay when you stay
The price is S$117 per night from 26 Nov to 27 Nov
S$117
26 Nov - 27 Nov
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"Have stayed here twice and plan ti return next month. Everything was wonderful"

Reviewed on 8 Nov, 2026

Best Western Plus Covered Bridge Inn
See all 194 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

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 holiday package cost?
You'll find cheap prices on Expedia for your Greencastle getaway. However, a range of factors like the hotel choice, length of stay and season will determine how much your holiday to Greencastle costs.
What are the cheapest months to go to Greencastle?
You're likely to find reduced prices and greater availability in January, March and August. Explore our cheap Greencastle holiday packages and you could get some great off-season discounts.
How many days is enough for Greencastle?
Typically, a handful of days is enough to explore the major attractions during your Greencastle holiday. However, if you want to have more time to kick back or take day trips, think about extending your trip.
Is it worth booking a holiday package to Greencastle?
Well known for its walking trails, hiking and festivals, a Greencastle holiday is a hit with all kinds of travellers. Be sure to check out leading sights like DePauw Nature Park and Putnam County Fairgrounds, and consider renting some wheels for day trips to discover even more.
How to find the best Greencastle package deals?
Begin your search for a Greencastle package deal by entering your destination and travel dates under our "Packages" tab. Then apply some filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Greencastle package deal right away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Greencastle getaway off to a flying start.
Is it cheaper to book a Greencastle holiday as a package?
An Expedia holiday package could land you considerable savings when compared to arranging flights and stays separately. Better still, you can customise your Greencastle escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a holiday package to Greencastle?
Land amazing discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for an impromptu Greencastle adventure.
How to plan a trip to Greencastle?

  1. Pick your travel dates: The things you plan to do in Greencastle and your preferred season will help you decide when to go.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and dining out to activities and flights. Your hotel will probably be the largest expense during your trip to Greencastle.
  3. Decide your trip length: Consider how much time you'd like to spend discovering Greencastle. Plan your days so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  4. Bundle your airfare and accommodation: Once you've nailed down your travel dates and duration, book the ideal Greencastle holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.