Southern Highlands Holidays from NZ$1,358
Book a Hotel + Flight or Car together to unlock savings
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- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
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The Latest Southern Highlands Holiday Packages
- Stylish 2-bed House With Private Courtyard
10 Sept - 14 SeptStylish 2-bed House With Private Courtyard + Flight
Redfern4 nights2.5 star property10/10 - Exceptional (1 review)"Excellent place for us to use as a base for vivisting Sydney for a short holiday. 5-10min walk from Redfern railway station meaning it was easy to move around the city. "Reviewed May 5, 2026Return • Auckland (AKL) - Sydney (SYD)AKL - SYD • Direct SYD - AKL • Direct - YEHS Hotel Sydney CBD
22 Sept - 28 SeptYEHS Hotel Sydney CBD + Flight
Sydney Central Business District6 nights3.5 star property8.4/10 - Very good (1,004 reviews)Return • Auckland (AKL) - Sydney (SYD)AKL - SYD • Direct SYD - AKL • Direct - Thriving City Location, Dining hub Near CBD
6 Sept - 11 SeptThriving City Location, Dining hub Near CBD + Flight
Pyrmont5 nights2.5 star propertyReturn • Auckland (AKL) - Sydney (SYD)AKL - SYD • Direct SYD - AKL • Direct - Spacious Inner-city House With Balcony Views
3 Sept - 6 SeptSpacious Inner-city House With Balcony Views + Flight
Millers Point3 nights2.5 star property9.0/10 - Wonderful (2 reviews)"."Reviewed July 15, 2026Return • Auckland (AKL) - Sydney (SYD)AKL - SYD • Direct SYD - AKL • Direct - North-east Facing Modern 2-bed Apartment
10 Sept - 14 SeptNorth-east Facing Modern 2-bed Apartment + Flight
Freshwater4 nights2.5 star propertyReturn • Auckland (AKL) - Sydney (SYD)AKL - SYD • Direct SYD - AKL • Direct
Discover the most popular places to visit in Southern Highlands
What to do in Southern Highlands
Personalised wine tour experience in the beautiful NSW Southern Highlands
Sydney Wine Tasting & Southern Highlands with Pick up & drop off
Southern Highlands Hotel Deals
The Dormie House - On The Golf Course
The Dormie House - On The Golf Course
Frequently Asked Questions
How much does a Southern Highlands holiday package cost?
Get your credit card ready, because a getaway to Southern Highlands starts from an affordable NZ$1,358. When you bundle your flights, hotels and car rentals into a holiday package, you'll score great deals.
How do I get a cheap travel package to Southern Highlands?
Booking a Southern Highlands holiday package with Expedia is one of the easiest ways to save. We offer access to over 550 airlines and 1 000 000 properties across the globe. With such a fabulous range to pick from, you'll have no trouble creating your dream trip.
What are the top hotels in Southern Highlands?
Briars Country Lodge and Berida Hotel know how to make their guests feel at home in Bowral. If your itinerary also includes Mittagong, look up Mittagong Motel and Cabin - Mittagong Caravan Park. Both are popular with travellers.
How far in advance should I book my Southern Highlands holiday?
Earlier is always better. Airlines usually advertise flights up to a year prior to departure, and this is a great opportunity to land some rock-bottom prices. Boss just told you to use up some holiday time next month? No need to worry. Expedia are never short of fantastic deals to help you have the getaway of your dreams, at a price you can afford.
What does an Expedia Southern Highlands travel package include?
Much of that depends on you. You can choose from a variety of Southern Highlands packages, such as a flight, rental car and hotel. You can also book a flight with a hotel, or a flight and a rental car. Once you've made your booking, you can add on the fun stuff like activities and experiences. Whatever your perfect Southern Highlands break looks like, get set to save!
What should I know before booking a Southern Highlands travel package?
Bundling your bookings into a Southern Highlands holiday package is the most convenient way to organise your trip. Not only that, you'll save just for combining your hotels, flights and car rentals. Once you've booked, why not add on a day tour or an activity?
Can I choose my airline with a Southern Highlands Expedia holiday package?
You can, and with more than 550 airlines to select from globally, you're not short on choice. Take a look at the available options and find out which airline fits your needs and budget.
If I'm not able to travel, can I cancel my Southern Highlands holiday package?
Yes you can, and we'll help you every step of the way. You may be able to change or cancel your Southern Highlands holiday package at no cost within 24 hours of booking. But you may incur a fee from your hotel, airline or car rental company if your booking is older than that. If life throws you a curveball, visit our Customer Service Portal for further information.