Southwest Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Top Southwest Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Pittsburgh Marriott City Center
Downtown Pittsburgh
CA $1,061
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Pittsburgh (PIT)
8.2/10 Very good! (1,330 reviews)
Excellent t room…large with a king and pull out. More space than usual … clean… loved the deco feel… bar and restaurant great loved the location… walking distances to a lot of places!
Reviewed on Oct 3, 2026
The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
CA $1,266
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Pittsburgh (PIT)
8.6/10 Excellent! (1,000 reviews)
Great location. Super comfortabke pillows and bed.
Gym is fantastic.
Would return
Reviewed on Oct 3, 2026
Ready to book your vacation to Southwest?
Southwest Hotel Deals
Log Cabin Lodge & Suites
288 Route 711 Jones Mills PA
Fully refundableReserve now, pay when you stay
CA $149
CA $171 total
Oct 11 - Oct 12
includes taxes & fees
Holiday Inn Express Irwin (Pa Tpk Exit 67) by IHG
8400 Route 30 Irwin PA
Fully refundable
CA $158
CA $176 total
Nov 1 - Nov 2
includes taxes & fees
8.2/10 Very good! (681 reviews)
"Very comfortable beds, great breakfast with to go boxes available, fresh ground coffee. Overall excellent stay for a quick stopover."
Reviewed on Oct 2, 2026
Slopeside Hotel, A Vail Resorts Property
777 Water Wheel Dr Champion PA
Fully refundableReserve now, pay when you stay
CA $224
CA $276 total
Nov 3 - Nov 4
includes taxes & fees
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.
Frequently asked questions
How much does a Southwest vacation package cost?
Offering excellent value package deals from CA $1,061 on Expedia, you'll be pleasantly surprised at how much a vacation to Southwest costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Southwest?
January, February and March are great times to search for cheap Southwest vacation packages. Choosing to travel in less busy periods means you'll typically find lower prices on flights and accommodations.
How many days is enough for Southwest?
With a well-organized schedule, you can easily tick off the main Southwest attractions in a handful of days. But if you'd like to discover lesser-known spots or go on day trips, consider booking your Southwest vacation for longer.
How to find the best Southwest package deals?
Use Expedia's filters to find some unbeatable Southwest package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Southwest package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Southwest vacation as a package?
You can enjoy significant savings on your Southwest retreat by booking a personalized vacation package. Click on the "Package" heading, then enter your travel dates and destination to view the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Southwest?
If you're planning an impromptu Southwest vacation, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can score amazing deals on your hotels and flights by booking ahead.
How to plan a trip to Southwest?
- Choose the right time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to travel to Southwest.
- Budget wisely: As well as the cost of your hotel, you should consider other expenses too. These include flights, food and transportation. Also, set aside a little extra for unexpected costs that could crop up during your trip to Southwest.
- Work out your trip length: Consider how long you want to spend discovering Southwest. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
- Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a customized Southwest vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
