Southwest Vacations from $625

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Your Southwest Vacation

Planning your next exciting adventure is a walk in the park with a Southwest vacation package. The neighborhood of South Greensburg, which is great for dining, makes a superb base to uncover the marvels of this vibrant city. Every trip to Southwest needs a well-designed itinerary. Fill yours with major attractions like Duncan House at Polymath Park Resort, Mount Pleasant Glass Museum and Greendance Winery. Whatever your travel plans or budget, organizing a tailored Southwest vacation is simple with Expedia.

The Latest Southwest vacation packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Pittsburgh - Green Tree

DoubleTree by Hilton Pittsburgh - Green Tree

4 out of 5
Price was $721, price is now $625 per person
$625
per person
Dec 30 - Jan 3
found 6 hours ago
Roundtrip flight included
Houston (IAH) to Pittsburgh (PIT)
8.8/10 Excellent! (1,271 reviews)

Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was $1,286, price is now $858 per person
$858
per person
Nov 26 - Nov 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
8/10 Very Good! (339 reviews)
The building and unit were very clean and the unit we stayed seemed newly renovated with new furniture. Very spacious and had everything we needed.

Reviewed on Oct 26, 2026

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was $1,096, price is now $939 per person
$939
per person
Jan 13 - Jan 17
found 24 hours ago
Roundtrip flight included
Houston (HOU) to Pittsburgh (PIT)
8.6/10 Excellent! (1,001 reviews)
My go to hotel when I’m in Pittsburgh. Easy to get to, parking garage right below the hotel, and great location with a ton of places within walking distance.

Reviewed on Oct 25, 2026

Omni William Penn Hotel

Omni William Penn Hotel

4 out of 5
Downtown Pittsburgh
Price was $1,017, price is now $880 per person
$880
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
9.2/10 Wonderful! (2,009 reviews)
Our first time stay and everything was excellent, including the food. Our Ambassador was very helpful and accomodating.

Reviewed on Oct 26, 2026

Etage Executive Living

Etage Executive Living

3.5 out of 5
Downtown Pittsburgh
Price was $1,078, price is now $933 per person
$933
per person
Dec 30 - Jan 3
found 6 hours ago
Roundtrip flight included
Houston (IAH) to Pittsburgh (PIT)
9.2/10 Wonderful! (1,909 reviews)
Great location parking room and view!

Reviewed on Oct 26, 2026

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Southwest Hotel Deals

Log Cabin Lodge & Suites

Log Cabin Lodge & Suites

2 out of 5
288 Route 711 Jones Mills PA
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $102 total per night from Nov 16 to Nov 17
$102 total
Nov 16 - Nov 17
Total with taxes and fees
9/10 Wonderful! (1,004 reviews)
"The hotel was clean and it was dog friendly. We were given a handicapped room however and with the big tub in the living room the room was small for 2 adults and a full size dog."

Reviewed on Oct 26, 2026

Log Cabin Lodge & Suites
Slopeside Hotel, A Vail Resorts Property

Slopeside Hotel, A Vail Resorts Property

4.5 out of 5
777 Water Wheel Dr Champion PA
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $204 total per night from Nov 2 to Nov 3
$204 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (532 reviews)
"Room was clean and comfortable. Great view. Plenty of shops and activities to enjoy."

Reviewed on Oct 24, 2026

Slopeside Hotel, A Vail Resorts Property
Super 8 by Wyndham New Stanton

Super 8 by Wyndham New Stanton

2 out of 5
103 Bair Blvd New Stanton PA
Fully refundableReserve now, pay when you stay
$65 nightly
The price is $73 total per night from Nov 1 to Nov 2
$73 total
Nov 1 - Nov 2
Total with taxes and fees
Super 8 by Wyndham New Stanton
See all 724 properties in Southwest
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.

Find the Best Southwest Vacation Packages

Southwest Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Arnold Palmer Regional Airport (LBE)
Top Sights
Greendance Winery, Mulberry Hill Golf Course and Mount Pleasant Glass Museum

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Frequently asked questions

How much does a Southwest vacation package cost?
Offering excellent value package deals from $625 on Expedia, you'll be surprised at how little a vacation to Southwest costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Southwest?
You're likely to find reduced prices and greater availability in November, December and January. Browse our cheap Southwest vacation packages and you could land some great off-season deals.
How many days is enough for Southwest?
Generally, a handful of days is enough to see the major sights during your Southwest vacation. However, if you want to have more time to chill out or take day trips, think about extending your trip.
How to find the best Southwest package deals?
Bagging a cheap Southwest package deal is a cinch with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a couple of filters and browse what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to view the most wallet-friendly Southwest package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Southwest vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging accommodations and flights individually. Better still, you can customize your Southwest escape to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Southwest?
If you're planning a spontaneous Southwest trip, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can score terrific deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Southwest vacation packages?
If you're like us, you love discovering new places but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Southwest trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.