Southwest Vacations from $362

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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.
Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Price was $460, price is now $362 per person
$362
per person
Jun 22 - Jun 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.2/10 Very Good! (3,551 reviews)
The room was clean and had a great view of the river!

Reviewed on May 23, 2026

Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was $695, price is now $526 per person
$526
per person
Jul 24 - Jul 26
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8/10 Very Good! (280 reviews)
This was a perfect arrangement for our short visit to Pittsburgh. Clean and functional.

Reviewed on May 20, 2026

Fairmont Pittsburgh

Fairmont Pittsburgh

4.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $1,133, price is now $858 per person
$858
per person
Jul 6 - Jul 10
found 14 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.8/10 Excellent! (1,003 reviews)
The room was beautiful and clean ! Very spacious and comfortable. The bathroom was very clean , very big and also bright ! Lighting was very good !

Reviewed on May 22, 2026

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was $501, price is now $388 per person
$388
per person
Jun 22 - Jun 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.4/10 Very Good! (1,492 reviews)
Convenient location w nice room.

Reviewed on May 19, 2026

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

4 out of 5
Downtown Pittsburgh
Price was $593, price is now $471 per person
$471
per person
Aug 14 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
8.2/10 Very Good! (1,066 reviews)
Hotel was clean and within waking distance to everything. We enjoyed our stay there.

Reviewed on May 22, 2026

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Discover the most popular places to visit in Southwest

Greendance Winery

4.5/5(7 reviews)

You can enjoy a tasting or tour at Greendance Winery during your travels to Mount Pleasant. You can seek out the hiking trails and campsites in this family-friendly area.

Greendance Winery

Mount Pleasant Glass Museum

You can study the exhibits at Mount Pleasant Glass Museum, a museum with a story of its own, during your trip to Mount Pleasant. Stroll along the riverfront in this family-friendly area, or seek out the hiking trails.

Mount Pleasant Glass Museum

Mulberry Hill Golf Course

Enjoy a round of golf in Mount Pleasant at Mulberry Hill Golf Course. Stroll along the riverfront or seek out the biking trails.

Mulberry Hill Golf Course

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
$98 nightly
The price is $109 total per night from May 26 to May 27
$109 total
May 26 - May 27
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
"I love stay there, rooms are very clean, the staff is great, the air conditioning is very comfortable! Nice quite place you can relax and just enjoy!!"

Reviewed on May 18, 2026

Log Cabin Lodge & Suites
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
$70 nightly
The price is $77 total per night from Jun 2 to Jun 3
$77 total
Jun 2 - Jun 3
Total with taxes and fees
8/10 Very Good! (1,001 reviews)
"I got in late. There was no issue checking in. The room was perfect. I slept hard and missed bfast. I will stay here again"

Reviewed on May 22, 2026

Super 8 by Wyndham New Stanton
Holiday Inn Express & Suites Belle Vernon by IHG

Holiday Inn Express & Suites Belle Vernon by IHG

2.5 out of 5
181 Finley Rd Belle Vernon PA
Fully refundable
$93 nightly
The price is $103 total per night from Jun 21 to Jun 22
$103 total
Jun 21 - Jun 22
Total with taxes and fees
Holiday Inn Express & Suites Belle Vernon by IHG
See all 696 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 $362 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.