Southwest Holidays

  • Plan, book, travel with confidence

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Southwest Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
per person
17 Sept - 21 Sept
found 1 day ago
Return flight included
Boston (BOS) to Pittsburgh (PIT)
8.4/10 Very Good! (1,334 reviews)
Bike rental was fun. Friday night restaurant was closed at 9:45 pm when advertised to be open until 10.

Reviewed on 15 Aug, 2025

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
per person
17 Sept - 21 Sept
found 1 day ago
Return flight included
Boston (BOS) to Pittsburgh (PIT)
8.6/10 Excellent! (1,002 reviews)
Location, location, location. The property layout is super convenient with easy access to the convention center and local amenities. Like many properties, I felt the room was not as updated and fresh as the public areas were. Check-in was extremely fast and efficient. The value is in the proximity to the freeway and downtown life.

Reviewed on 22 Jun, 2025

Omni William Penn Hotel

Omni William Penn Hotel

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
per person
17 Sept - 21 Sept
found 1 day ago
Return flight included
Boston (BOS) to Pittsburgh (PIT)
9/10 Wonderful! (1,582 reviews)
Nice and great staff. Good location

Reviewed on 13 Aug, 2025

Fairmont Pittsburgh

Fairmont Pittsburgh

4.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
per person
17 Sept - 21 Sept
found 1 day ago
Return flight included
Boston (BOS) to Pittsburgh (PIT)
8.8/10 Excellent! (1,002 reviews)
Everything was great

Reviewed on 12 Aug, 2025

Sheraton Pittsburgh Hotel at Station Square

Sheraton Pittsburgh Hotel at Station Square

3.5 out of 5
South Shore
per person
17 Sept - 21 Sept
found 1 day ago
Return flight included
Boston (BOS) to Pittsburgh (PIT)
8.8/10 Excellent! (1,000 reviews)
They paid attention to what updates they implemented.

Reviewed on 15 Aug, 2025

Top hotels in Southwest

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
The price is S$150 per night from 19 Aug to 20 Aug
S$150
19 Aug - 20 Aug
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"We stay in the Jacuzzi room. Twice a year for a weekend stay. Its a relaxing stay."

Reviewed on 12 Aug, 2025

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
The price is S$162 per night from 1 Sept to 2 Sept
S$162
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (830 reviews)
Perfect place to sleep.
"Clean, new, friendly. Cold aC. Can't go wrong."

Reviewed on 14 Aug, 2025

Hampton Inn & Suites North Huntingdon-Irwin
The Inn at Mountainview

The Inn at Mountainview

2 out of 5
300 Scenery Lane, Greensburg, PA
Fully refundableReserve now, pay when you stay
7.8/10 Good! (1,001 reviews)
"Too much noise coming from the hallway..."

Reviewed on 14 Aug, 2025

Get rates
The Inn at Mountainview
See all 638 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.

Frequently asked questions

How much does a Southwest holiday package cost?
Offering excellent value package deals from S$680 on Expedia, you'll be surprised at how little a holiday to Southwest costs! Our packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Southwest?
You can typically find lower rates and greater availability in January, February and March. Take a look at our cheap Southwest holiday packages and you could land some great off-season deals.
How many days is enough for Southwest?
The ideal length for your Southwest holiday depends on what you'd like to do and see. Generally, a few days to a week will give you enough time to go to all the main sights and discover some hidden gems along the way.
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," "Traveller 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 travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Southwest holiday as a package?
An Expedia holiday package could land you great savings when compared to arranging accommodation and flights individually. Better still, you can customise 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 holiday 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.
How to plan a trip to Southwest?

  1. Choose your dates: What you'd like to do in Southwest and your favourite season will help you decide when to go.
  2. Work out your budget: Make sure you have enough money to cover everything from transportation and food to experiences and flights. Your hotel will likely be the largest expense during your trip to Southwest.
  3. Decide your trip length: Consider how long you'd like 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.
  4. Bundle your airfare and accommodation: After you've settled on your trip dates and duration, lock in the right Southwest holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.