Greencastle Vacation Packages 2026 from $326

Greencastle flight + hotel vacation packages

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

Holiday Inn Express Hotel & Suites Greenwood by IHG

$326

per person

Nov 2 - Nov 5

found 15 hours ago

Roundtrip flight included

Orlando (MCO) to Indianapolis (IND)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Omni Severin Hotel

Downtown Indianapolis

$512

per person

Nov 2 - Nov 5

found 15 hours ago

Roundtrip flight included

Orlando (MCO) to Indianapolis (IND)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.

Hotel Indy, Indianapolis, a Tribute Portfolio Hotel

Downtown Indianapolis

$472

per person

Nov 2 - Nov 5

found 15 hours ago

Roundtrip flight included

Orlando (MCO) to Indianapolis (IND)

This hotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. Valet parking is offered and the front desk is staffed around-the-clock.

Embassy Suites by Hilton Indianapolis North

College Park

$364

per person

Nov 2 - Nov 5

found 15 hours ago

Roundtrip flight included

Orlando (MCO) to Indianapolis (IND)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.

Best Location 5 BD Spacious Family Home- Indianapolis IN

$1,227

per person

Nov 7 - Nov 9

found 1 day ago

Roundtrip non-stop flight included

Philadelphia (PHL) to Indianapolis (IND)

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and barbecue grills are also provided.

Top Greencastle hotels deals

Inn at DePauw

2 West Seminary Street Greencastle IN

$160 nightly

$179 total

Sep 13 - Sep 14

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a terrace, and a lobby fireplace are also offered.

Pet friendly

Parking included

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

Greencastle IN

$230 nightly

$258 total

Aug 26 - Aug 27

Total with taxes and fees

A hot tub is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.

Hot Tub

Kitchen

Cozy 1-Bedroom Retreat Near DePauw University & Downtown Greencastle!

Greencastle IN

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This apartment features laundry facilities.

Washer

Dryer

Secluded Cabin in the Woods, Private Nature Retreat Near Greencastle & I-70

Greencastle IN

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This cabin includes a garden and laundry facilities.

Kitchen

Washer

Days Inn by Wyndham Cloverdale Greencastle

1031 N. Main St. Cloverdale IN

Free Cancellation

Reserve now, pay when you stay

$75 nightly

$84 total

Aug 27 - Aug 28

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. A 24-hour gym and a computer station are also provided.

Breakfast included

Pet friendly

Best Western Plus Covered Bridge Inn

3882 N State Road 59 Brazil IN

Free Cancellation

Reserve now, pay when you stay

$85 nightly

$91 total

Sep 7 - Sep 8

Total with taxes and fees

This hotel features a gym and a seasonal outdoor pool. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Express check-out and a safe deposit box are also provided.

Pool

Breakfast included

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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.

Stay near popular Greencastle attractions

Putnam County Fairgrounds

8.2/10 (31 reviews)

Take the family on an outing to Putnam County Fairgrounds during your trip to Greencastle. Take in the festivals while you're in the area.

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Frequently asked questions

How much are vacation packages to Greencastle?

Travelocity offers hotel and flight vacation packages from just $326. With these kinds of savings, you'll be saying hello to Greencastle in a flash.

How long should my Greencastle vacation be?

Your Greencastle trip can be as long or as short as you want, but many people stay around 2 nights. In the mood to venture off the beaten path and uncover some lesser-known sights? Book a few extra nights and experience a different side of this place.

Where can I get the best vacation package deals for Greencastle?

It's difficult to beat Travelocity when it comes to finding your Greencastle package deal. There are at least 400 partner airlines and 1,000,000 worldwide properties to choose from. Book your vacation now and get ready to tick another place off your travel bucket list.

Why should I book my Greencastle vacation bundle via Travelocity?

We've got 24/7 customer support, excellent service and a Price Match Guarantee. Life's a big journey — and we have enticing destinations for you to journey to all around the world. Roam with us and your wallet will thank you for it.

Can I save on my Greencastle car rental if I bundle it with hotels and flights?

With a Greencastle vacation package, you can bundle your car, hotel and flight bookings and save a ton. When you're ready to discover the best of this impressive part of the world, why not start with Indianapolis Motor Speedway? This famous attraction is 35 mi from Greencastle. With your own rental car, you'll be there in a flash.

Which airport is best for Greencastle?

Indianapolis Intl. Airport (IND) is the top airport if you're flying to Greencastle. Once you get there, you'll find yourself 30 mi east of the center of town.

What is there to do in Greencastle?

While venturing off the beaten track is no doubt rewarding, you shouldn't ignore the popular sights that make a destination famous. DePauw University and DePauw Nature Park are just two of them in Greencastle.

Where should I stay when visiting Greencastle?

Many visitors choose to hit the hay at the Inn at DePauw. It's sure to be a good base for your Greencastle escape.