Southwest Vacations from $489

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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 Washington Meadow Lands Casino Area

DoubleTree by Hilton Washington Meadow Lands Casino Area

4 out of 5
Price was $638, price is now $489 per person
$489
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Pittsburgh (PIT)
7.8/10 Good! (825 reviews)
This is a fine hotel, for the price, but there's nothing exceptional about it. It's definitely dated and they are doing an upgrade but they really should have shutdown while they do it. We were awakened by hammering right below our bed at 8 am. Overall, it's good enough but don't expect a lot. The outdoor pool is decent though.

Reviewed on Jul 10, 2025

TRYP by Wyndham Pittsburgh/Lawrenceville

TRYP by Wyndham Pittsburgh/Lawrenceville

3 out of 5
Lawrenceville
Save 100% on your flight
Price was $1,075, price is now $815 per person
$815
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Pittsburgh (PIT)
8.6/10 Excellent! (894 reviews)
Very cute, swanky hotel. Just didn’t have fridge or microwave in the room.

Reviewed on Aug 30, 2025

Melwood Suites Unit 107 Studio

Melwood Suites Unit 107 Studio

2 out of 5
Oakland
Save 100% on your flight
Price was $645, price is now $489 per person
$489
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
9.6/10 Exceptional! (30 reviews)
Elegant place with everything organized extremely well!

Reviewed on Jul 25, 2025

TownePlace Suites by Marriott Pittsburgh Cranberry Township

TownePlace Suites by Marriott Pittsburgh Cranberry Township

3 out of 5
Price was $787, price is now $605 per person
$605
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Pittsburgh (PIT)
9.2/10 Wonderful! (405 reviews)
The building is in good shape. One piece of furniture in our room was in poor shape but the rest of the room was fine and our stay was good. The breakfast is basic but sufficient.

Reviewed on Aug 17, 2025

Hampton Inn Pittsburgh/Monroeville

Hampton Inn Pittsburgh/Monroeville

2.5 out of 5
Price was $783, price is now $611 per person
$611
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Pittsburgh (PIT)
8/10 Very Good! (1,062 reviews)
Attached Restaurant great staff

Reviewed on Aug 29, 2025

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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
$92 nightly
The price is $102 total per night from Sep 25 to Sep 26
$102 total
Sep 25 - Sep 26
Total with taxes and fees
Log Cabin Lodge & Suites
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
$128 nightly
The price is $142 total per night from Sep 30 to Oct 1
$142 total
Sep 30 - Oct 1
Total with taxes and fees
Hampton Inn & Suites North Huntingdon-Irwin
Red Roof Inn Greensburg

Red Roof Inn Greensburg

2 out of 5
111 Sheraton Dr Rt 30, Greensburg, PA
Fully refundableReserve now, pay when you stay
$82 nightly
The price is $92 total per night from Sep 8 to Sep 9
$92 total
Sep 8 - Sep 9
Total with taxes and fees
Red Roof Inn Greensburg
See all 637 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.

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Frequently asked questions

How much does a Southwest vacation package cost?
Offering excellent value package deals from $489 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.