Southwest Vacations from $305

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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.
Ambridge Inn

Ambridge Inn

3 out of 5
Price was $398, price is now $305 per person
$305
per person
Feb 25 - Mar 1
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8/10 Very Good! (96 reviews)
Friendly staff. Clean room

Reviewed on Nov 28, 2025

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $732, price is now $492 per person
$492
per person
Feb 25 - Mar 1
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.2/10 Very Good! (3,142 reviews)
Didn’t have breakfast but I’m sure it would’ve been delicious! Great location, walkable to everything you need from the Acrisure Stadium to area dining & shopping!

Reviewed on Jan 19, 2026

Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
East Liberty
Price was $446, price is now $324 per person
$324
per person
Feb 25 - Mar 1
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8/10 Very Good! (1,003 reviews)
Staff was extremely kind, friendly and helpful! The space was clean and beautiful! The breakfast was delicious!

Reviewed on Jan 11, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was $651, price is now $487 per person
$487
per person
Apr 2 - Apr 5
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
7.6/10 Good! (37 reviews)
Kitchen was fully equipped with everything you would need. The rooms were clean and spacious, beautiful building and friendly staff. Parking is what you would expect in a downtown area but was very easy and the attendant was great.

Reviewed on Jan 14, 2026

DoubleTree by Hilton Pittsburgh - Cranberry

DoubleTree by Hilton Pittsburgh - Cranberry

4 out of 5
Price was $615, price is now $468 per person
$468
per person
Feb 25 - Mar 1
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.8/10 Excellent! (913 reviews)
Awesome and helpful front desk staff!

Reviewed on Jan 5, 2026

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Discover the most popular places to visit in Southwest

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

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

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
$101 nightly
The price is $113 total per night from Feb 8 to Feb 9
$113 total
Feb 8 - Feb 9
Total with taxes and fees
9/10 Wonderful! (1,004 reviews)
It was very nice, stayed in the Timber Suite. Highly recommend this place!

Reviewed on Jan 12, 2026

Log Cabin Lodge & Suites
Slopeside Hotel by Seven Springs Resort

Slopeside Hotel by Seven Springs Resort

4.5 out of 5
777 Water Wheel Dr Champion PA
$179 nightly
The price is $199 total per night from Feb 16 to Feb 17
$199 total
Feb 16 - Feb 17
Total with taxes and fees
8.6/10 Excellent! (392 reviews)
Great staff and the room was very nice.

Reviewed on Jan 16, 2026

Slopeside Hotel by Seven Springs Resort
Hampton Inn & Suites North Huntingdon-Irwin

Hampton Inn & Suites North Huntingdon-Irwin

2.5 out of 5
8441 Country Club Drive Irwin PA
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $131 total per night from Feb 1 to Feb 2
$131 total
Feb 1 - Feb 2
Total with taxes and fees
9.2/10 Wonderful! (959 reviews)
Clean room

Reviewed on Jan 16, 2026

Hampton Inn & Suites North Huntingdon-Irwin
See all 697 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 $305 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.