Penn Vacations from $290

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Your Penn Vacation

Organizing your next big getaway is a cinch with a Penn vacation package. The neighborhood of South Greensburg, which is great for dining, makes a good launchpad to discover the delights of this unique city. Make your trip to Penn even more fulfilling by going sightseeing. Seton Hill University, The Palace Theatre and Westmoreland Museum of American Art are some of the major attractions you'll want to explore. A couple of quick clicks is all it takes to put together the perfect Penn vacation on Expedia.

The Latest Penn vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
East Liberty
Save 100% on your flight
Price was $453, price is now $290 per person
$290
per person
Nov 15 - Nov 17
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Pittsburgh (PIT)
8.2/10 Very Good! (1,006 reviews)
Changed rooms 3 times as TV wasn’t working. Coffee machine not working. Easy to walk to restaurants. Quiet.

Reviewed on Aug 24, 2025

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $595, price is now $384 per person
$384
per person
Nov 15 - Nov 17
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Pittsburgh (PIT)
8.2/10 Very Good! (3,005 reviews)
I liked the location, very walkable area. The hotel itself has had updates. They need to add USB ports. A TV channel guide might be nice. But the staff is excellent. ALL very helpful, informative, and accommodating. I was there on a very busy weekend and

Reviewed on Sep 2, 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $574, price is now $391 per person
$391
per person
Nov 15 - Nov 17
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Pittsburgh (PIT)
8.4/10 Very Good! (1,345 reviews)
Great dog friendly location. Nice room

Reviewed on Aug 30, 2025

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $632, price is now $450 per person
$450
per person
Nov 15 - Nov 17
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Pittsburgh (PIT)
8.6/10 Excellent! (1,003 reviews)
The property was great the and the sfaff were awesome.

Reviewed on Aug 17, 2025

Kimpton Hotel Monaco Pittsburgh by IHG

Kimpton Hotel Monaco Pittsburgh by IHG

4.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $904, price is now $677 per person
$677
per person
Nov 15 - Nov 17
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Pittsburgh (PIT)
9.4/10 Exceptional! (1,214 reviews)
This was our first time in Pittsburgh and our stay at the Hotel Monaco was pleasant.

Reviewed on Sep 1, 2025

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Penn Hotel Deals

Courtyard by Marriott Pittsburgh University Center

Courtyard by Marriott Pittsburgh University Center

3.5 out of 5
100 Lytton Avenue, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $158 total per night from Sep 4 to Sep 5
$158 total
Sep 4 - Sep 5
Total with taxes and fees
Courtyard by Marriott Pittsburgh University Center
Hampton Inn Pittsburgh/Monroeville

Hampton Inn Pittsburgh/Monroeville

2.5 out of 5
3000 Mosside Blvd, Monroeville, PA
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $115 total per night from Sep 21 to Sep 22
$115 total
Sep 21 - Sep 22
Total with taxes and fees
Hampton Inn Pittsburgh/Monroeville
Hyatt House Pittsburgh/Bloomfield/Shadyside

Hyatt House Pittsburgh/Bloomfield/Shadyside

3 out of 5
5335 Baum Blvd, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $181 total per night from Sep 28 to Sep 29
$181 total
Sep 28 - Sep 29
Total with taxes and fees
Hyatt House Pittsburgh/Bloomfield/Shadyside
See all 702 properties in Penn
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.

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Frequently asked questions

How much does a Penn vacation package cost?
You'll find cheap prices from $290 on Expedia for your Penn escape. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Penn costs.
What are the cheapest months to go to Penn?
You can usually find lower rates and better availability in November, December and January. Explore our cheap Penn vacation packages and you could get some excellent off-season deals.
How many days is enough for Penn?
Usually, a handful of days is enough to see the main attractions during your Penn vacation. However, if you prefer to have some time to rest or go on day tours, think about extending your trip.
How to find the best Penn package deals?
Finding a cheap Penn package deal is easy with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can tailor your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most affordable Penn package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Penn vacation as a package?
An Expedia vacation package could land you great savings when compared to booking stays and flights individually. Better still, you can customize your Penn getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Penn?
If you have your Penn vacation dates confirmed, book as early as you can to grab some fantastic deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are great for impromptu escapes.
Does Expedia offer Book Now, Pay Later Penn vacation packages?
Your Penn trip is meant to be an escape from your daily routine, not a reason for money-related stress. So to allow you a little more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.