A tall monument with a golden statue on top, surrounded by trees and a clear blue sky.

South Side Holidays from NZ$3,943

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$2,400 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

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

The Latest South Side Holiday Packages

Price found within the past 48 hours. Click for updated prices.
  • 18 Oct - 24 Oct

    Chelsea rooms + Flight

    Manhattan
    6 nights
    2.0 star property
    8.2/10 - Very good (27 reviews)
    Return Auckland (AKL) - New York (JFK)
    AKL - JFKDirect JFK - AKLDirect
    NZ$4,160
    NZ$3,943
    per traveller
    found 1 day ago
    Chelsea rooms
  • 18 Oct - 24 Oct

    Holiday Inn Manhattan 6th Ave - Chelsea by IHG + Flight

    Manhattan
    6 nights
    3.0 star property
    8.2/10 - Very good (1,067 reviews)
    "We enjoyed our stay. The room was perfect for our short stay in NYC. The beds were firm but felt really good after walking around all day. Other than the water pressure not being great and the door to the bathroom hard to close and open, it was just what we needed."
    Reviewed July 27, 2026
    Return Auckland (AKL) - New York (JFK)
    AKL - JFKDirect JFK - AKLDirect
    NZ$4,377
    NZ$4,036
    per traveller
    found 1 day ago
    Holiday Inn Manhattan 6th Ave - Chelsea by IHG
  • 18 Oct - 24 Oct

    Sonesta Simply Suites Jersey City + Flight

    Downtown Jersey City
    6 nights
    2.5 star property
    8.8/10 - Excellent (1,014 reviews)
    "The room was filthy. The floors didn’t appear to be vacuumed. I found crumbs and food. The sheets had stains on them. The bathtub/shower was grimy. The kitchen smelled like sewer. I wouldn’t stay again."
    Reviewed July 27, 2026
    Return Auckland (AKL) - New York (JFK)
    AKL - JFKDirect JFK - AKLDirect
    NZ$3,978
    NZ$3,965
    per traveller
    found 1 day ago
    Sonesta Simply Suites Jersey City

Discover the most popular places to visit in South Side

South Side Hotel Deals

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 South Side holiday package cost?

From as low as NZ$3,943, you can custom build your South Side holiday package. Simply combine flights, hotels and car rentals and we'll reward you with discounts.

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

One of the easiest ways to save dollars (and time) is to bundle your bookings with Expedia. Flights, hotels, rental cars and activities — we've got everything you need. Choose the combination that suits you and watch your savings grow. We know a package deal is never one-size-fits-all. That's why we offer over 550 airlines and 1 000 000 hotels across the globe, which lets you customize your South Side adventure.

Where should I stay in South Side?

A trip to South Side isn't complete without paying a visit to Montefiore Mount Vernon Hospital, St. Pauls Church National Historic Site and Willsons Woods Park. Spend your evenings close to these popular attractions and make sightseeing easy.

What are the top hotels in South Side?

Modern And Quiet Getaway is one of South Side's top properties. Secure a room here and you'll be able to rest easy knowing you're in excellent hands.

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

It's hard to pick the best time for airfares, but we usually say the earlier, the better. Many international flights on Expedia become available up to a year in advance. If you're booking last minute, fear not. Low prices appear from time to time just weeks before departure dates.

What does an Expedia South Side travel package include?

From hotels and flights to rental cars, Expedia can help you create a South Side package that's right for you. Holidaying for a week or longer? Give some thought to a flight, rental car and hotel bundle. If you can only manage a quick getaway, a hotel and flight deal could be what you're after. Tours and activities can be added after you've booked. Our holiday packages make it a breeze to save and plan.

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

Booking all the parts of your trip together is one of the best ways to save. Bundle your car rentals, airfares and hotels into one little package. But you're not limited to hotels. Expedia has all types of properties, including holiday homes such as beachfront villas and short-term homes. Your choices are almost endless!

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

Expedia offers access to more than 550 partner airlines worldwide, so you certainly can. Just select your favourite carrier and put together your ideal South Side getaway.

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

Don't worry if you're rethinking your South Side holiday package — you can cancel or change your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We realise your circumstances can suddenly change, so head to our Customer Service Portal if that happens. When you're ready to make changes, we'll be here to help.

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