A river with a rocky cliff and trees in the foreground.

South Side Holidays from £338

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*
  • Find the right fit

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

    Packages with flights are ATOL protected

The Latest South Side Holiday Packages

Price found within the past 48 hours. Click for updated prices.
  • 6 Oct - 10 Oct

    Western Executive Inn + Flight

    West End
    4 nights
    2.5 star property
    8.0/10 - Very good (354 reviews)
    "Nice place...no complaints...except breakfast would be nice"
    Reviewed July 16, 2026
    Return San Francisco (SFO) - Billings (BIL)
    SFO - BIL1 stop BIL - SFO1 stop
    £386
    £338
    per traveller
    found 8 hours ago
    Western Executive Inn
  • 6 Oct - 10 Oct

    Northern Hotel + Flight

    Downtown Billings
    4 nights
    4.0 star property
    9.6/10 - Exceptional (1,245 reviews)
    Return San Francisco (SFO) - Billings (BIL)
    SFO - BIL1 stop BIL - SFO1 stop
    £645
    £513
    per traveller
    found 8 hours ago
    Northern Hotel
  • 6 Oct - 10 Oct

    My Place Hotel - Billings, MT + Flight

    Southwest Corridor
    4 nights
    2.0 star property
    8.8/10 - Excellent (1,008 reviews)
    "Big room with kitchen, place was outdated but clean and spacious"
    Reviewed July 12, 2026
    Return San Francisco (SFO) - Billings (BIL)
    SFO - BIL1 stop BIL - SFO1 stop
    £483
    £422
    per traveller
    found 8 hours ago
    My Place Hotel - Billings, MT
  • 6 Oct - 10 Oct

    Country Inn & Suites by Radisson, Billings, MT + Flight

    Billings Heights
    4 nights
    3.0 star property
    8.4/10 - Very good (1,005 reviews)
    "Room waa veey clean and comfortable. Breakfast was decent. Hotel parking was tricky getting in and out but good parking lot"
    Reviewed July 11, 2026
    Return San Francisco (SFO) - Billings (BIL)
    SFO - BIL1 stop BIL - SFO1 stop
    £489
    £435
    per traveller
    found 8 hours ago
    Country Inn & Suites by Radisson, Billings, MT
  • 6 Oct - 10 Oct

    Baymont by Wyndham Billings + Flight

    West End
    4 nights
    2.5 star property
    6.2/10 - (1,001 reviews)
    "The room was clean and comfortable, staff was awesome. There were some damages to the room, holes in the bathroom doors and the toilet lid was cracked. Other than that was a great hotel."
    Reviewed July 15, 2026
    Return San Francisco (SFO) - Billings (BIL)
    SFO - BIL1 stop BIL - SFO1 stop
    £408
    £366
    per traveller
    found 8 hours ago
    Baymont by Wyndham Billings

Frequently Asked Questions

How much does a South Side travel package cost?

Explore the best of South Side from just £338. We offer a wonderful selection of rental cars, hotels and flights to suit your budget. Land even better deals when you add a few sightseeing activities to your package.

If I'm not able to travel, can I cancel my South Side travel package?

Because we understand life can be unpredictable, the answer is yes. For further details, visit our Customer Service Portal. But generally speaking, if you've made your booking in the last 24 hours, you may be able to cancel or change it free of charge. Your airline, hotel or car rental company may charge a fee if your booking is older than that.

How do I get a cheap travel package to South Side?

Think of all the amazing things you could do in South Side with extra cash in your wallet. Watch your savings stack up when you bundle your flights, hotels and other bookings into a South Side travel package. You have plenty of choice when you book with Expedia too. In fact, you can take your pick of over 550 air carriers and 1,000,000 hotels around the globe. Whether you're taking off with the whole family or flying solo, exploring South Side is better with a package.

Does Expedia offer Book Now, Pay Later South Side holidays?

Your bank balance shouldn't stop you from taking a holiday, so Expedia has come up with a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book an incredible getaway without hurting your hip pocket. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your break. Consider one of these flexible payment options:

  • Pay monthly holidays: Make your holiday dreams a reality sooner with Klarna's manageable monthly instalment plans. If paying just a small amount each month works for you, choose this option during the checkout process.
  • Pay in instalments holidays: Into the idea of paying down your holiday in multiple transactions? Then go for this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the total upfront) makes it easier to click that "book now" button, opt for a low deposit holiday payment plan with Klarna.

Where should I stay in South Side?

Stay where the action is. Many people like to book hotels in the vicinity of top attractions, like First Interstate Arena, MetraPark and Rocky Mountain College.

What are the top hotels in South Side?

If it's your first visit to South Side, reserve a room at Northern Hotel or Days Inn by Wyndham Billings. Both hotels will make you feel at home and are top options with lots of travellers.

How far in advance should I book my South Side holiday?

Travellers can normally look up international fares on Expedia within 12 months of the departure date. Booking at the last minute? With a bit of luck, it's still possible to nab an affordable ticket only weeks before your flight.

What does an Expedia South Side travel package include?

From hotels and flights to rental cars, Expedia can help you craft a South Side package that fits you. Heading away for a while? Check out a hotel, rental car and flight bundle. If you can only manage a quick getaway, an airfare and hotel deal could be what you're after. Experiences can also be added once you've made your booking. Our packages make it simple to save and plan.

What should I know before booking a South Side travel package?

You'll land excellent savings when you bundle your hotels, flights and rental cars into a travel package. Not just that, booking everything in one place just makes things easier. So why waste your money or time? Whether you're putting together a luxury romantic escape or a budget family adventure, browse our travel packages today.

Can I choose my airline with a South Side Expedia travel package?

With a travel package, you're the boss. Whether you're looking to fly to South Side in economy or business class, simply select from the available airline options. Expedia has access to over 550 partner airlines around the world.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.