Greencastle Vacation Packages 2026 from $419

Greencastle flight + hotel vacation packages

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

Wyndham Gettysburg Hotel & Conference Center

$419

per person

Oct 11 - Oct 15

found 11 hours ago

Roundtrip flight included

Chicago (ORD) to Harrisburg (MDT)

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 gym and perks like free self parking.

Liberty Mountain Lodging by Vail Resorts

Save 100% on your flight

$419

per person

Oct 11 - Oct 15

found 11 hours ago

Roundtrip flight included

Chicago (ORD) to Harrisburg (MDT)

A golf course and an indoor pool are featured at this resort. There's a free ski shuttle, and ski passes and ski storage are available on site. Relax with a drink at one of the 3 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.

The Lodges at Gettysburg

$452

per person

Oct 11 - Oct 15

found 11 hours ago

Roundtrip flight included

Chicago (ORD) to Harrisburg (MDT)

This lodge features a restaurant, a gym, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, a terrace, and a grocery/convenience store are also on offer.

Hotel Gettysburg

Gettysburg Historic District

Save 100% on your flight

$511

per person

Oct 11 - Oct 15

found 11 hours ago

Roundtrip flight included

Chicago (ORD) to Harrisburg (MDT)

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

Allenberry Resort

$477

per person

Oct 22 - Oct 25

found 18 hours ago

Roundtrip flight included

Chicago (ORD) to Harrisburg (MDT)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. There's a bar/lounge on site, and a coffee shop and laundry facilities are also provided.

Top Greencastle hotels deals

Super 8 by Wyndham Greencastle

735 Buchanan Trl E Greencastle PA

Free Cancellation

Reserve now, pay when you stay

$71 nightly

$79 total

Sep 13 - Sep 14

Total with taxes and fees

Free self parking is available and the motel's front desk is staffed around-the-clock. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A business center, a library, and a hair salon are also on offer.

Holiday Inn Express Greencastle by IHG

50 Pine Dr Greencastle PA

Free Cancellation

$91 nightly

$101 total

Oct 11 - Oct 12

Total with taxes and fees

A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Hawthorn Extended Stay by Wyndham Chambersburg

1123 Lincoln Way East Chambersburg PA

Free Cancellation

Reserve now, pay when you stay

$72 nightly

$80 total

Oct 11 - Oct 12

Total with taxes and fees

This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Fairfield Inn & Suites by Marriott Hagerstown

89 ALL STAR COURT Hagerstown MD

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$113 total

Sep 20 - Sep 21

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy the free buffet breakfast each morning.

La Quinta Inn & Suites by Wyndham Chambersburg

199 Walker Rd Chambersburg PA

Free Cancellation

Reserve now, pay when you stay

$95 nightly

$106 total

Sep 27 - Sep 28

Total with taxes and fees

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.

Country Inn & Suites by Radisson, Chambersburg, PA

399 Beddington Blvd Chambersburg PA

Free Cancellation

$63 nightly

$70 total

Oct 11 - Oct 12

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the 24-hour business center, express check-out, and conference space. Enjoy the indoor pool and conveniences like a 24-hour front desk and laundry facilities.

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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

Greencastle Coffee Roasters

7.8/10 (14 reviews)

Enjoy an outing to Greencastle Coffee Roasters during your stay in Greencastle. Check out the shops and top-notch restaurants in this romantic area.

See properties

Frequently asked questions

How much are vacation packages to Greencastle?

Travelocity offers hotel and flight packages starting at an incredible $419. With such amazing deals, you'll be saying hello to Greencastle in no time.

How long should my Greencastle vacation be?

Around 3 nights is the average amount of time travelers vacation in Greencastle. But the perfect trip length comes down to how many magical memories you want to create. Why not stay a bit longer and discover some off-the-beaten-path gems?

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

It's difficult to beat Travelocity when it comes to piecing together your Greencastle package deal. There are at least 400 air carriers and 1,000,000 worldwide properties to select from. Lock in your trip now and get ready to tick another amazing place off your list.

Why should I purchase my Greencastle vacation bundle via Travelocity?

From amazing destinations to fun experiences, we have everything you need to satisfy your travel desires. Our 24/7 support will also ensure you're being well taken care of before, during and after your vacation. And don't stress if you notice a lower price on your reservation, we'll match it. That's our Price Match Guarantee.

Can I save money on my Greencastle car rental if I book it with a hotel or flight?

With a Greencastle vacation package, you can combine your hotel, flight and car bookings and save tons. If you'd love to explore the best of this fantastic region, why not make tracks to White House? This renowned sight is 70 mi from Greencastle. With your own wheels, you'll be there soon enough.

Which airport is best for Greencastle?

Many fly into Washington Dulles Intl. Airport (IAD), 60 mi south of downtown Greencastle. Others prefer Harrisburg Intl. Airport (MDT) (60 mi away from central Greencastle) or Blair County Airport (AOO) (45 mi away from central Greencastle).

What is there to do in Greencastle?

Greencastle Coffee Roasters deserves to be on your must-see list. After you've crossed off this leading attraction, simply stroll the streets of Greencastle and experience what makes this exciting destination tick.

Where should I stay when visiting Greencastle?

Many visitors opt to check in to the Holiday Inn Express Greencastle, an IHG Hotel. It's sure to be a good base for your Greencastle getaway.