Southern Highlands Holidays from NZ$1,796

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The Latest Southern Highlands Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Spacious 3-bed With Alfresco Dining by Amenities

Spacious 3-bed With Alfresco Dining by Amenities

2 out of 5
Kingsford
Save 100% on your flight
Price was NZ$2,816, price is now NZ$1,796 per person
NZ$1,796
per person
23 Apr - 28 Apr
found 1 day ago
Return flight included
Auckland (AKL) to Sydney (SYD)
No reviews
Spacious Inner-city House With Balcony Views

Spacious Inner-city House With Balcony Views

2.5 out of 5
Millers Point
Save 100% on your flight
Price was NZ$8,679, price is now NZ$5,149 per person
NZ$5,149
per person
23 Apr - 30 Apr
found 1 day ago
Return direct flight included
Kerikeri (KKE) to Sydney (SYD)
No reviews
Quaint 3-bed Heritage Home in the Heart of Sydney

Quaint 3-bed Heritage Home in the Heart of Sydney

2.5 out of 5
Millers Point
Save 100% on your flight
Price was NZ$4,436, price is now NZ$2,718 per person
NZ$2,718
per person
25 May - 31 May
found 1 day ago
Return direct flight included
Wellington (WLG) to Sydney (SYD)
No reviews
Traditional 2-bed Terrace House in Millers Point

Traditional 2-bed Terrace House in Millers Point

2.5 out of 5
Millers Point
Save 100% on your flight
Price was NZ$5,007, price is now NZ$3,246 per person
NZ$3,246
per person
23 Apr - 30 Apr
found 1 day ago
Return direct flight included
Kerikeri (KKE) to Sydney (SYD)
No reviews
Harbourside - Unforgettable Destination

Harbourside - Unforgettable Destination

2.5 out of 5
McMahons Point
Save 100% on your flight
Price was NZ$4,324, price is now NZ$2,836 per person
NZ$2,836
per person
23 Apr - 30 Apr
found 1 day ago
Return direct flight included
Kerikeri (KKE) to Sydney (SYD)
No reviews

Our guide on where to stay in Southern Highlands

Find the best Southern Highlands areas and neighborhoods for the activities you enjoy most. Learn more about Southern Highlands
white fence with pink flowers nature photography

Moss Vale

1 out of top 10 points of interest in this area

Moss Vale is noteworthy for its golf courses, and you can make a stop at top attractions like Moss Vale Golf Club and Leighton Gardens.

Find hotels in Moss Vale

Southern Highlands Holiday

Our pick of the best Southern Highlands Hotel Deals

Park Proxi Gibraltar Bowral

Park Proxi Gibraltar Bowral

4 out of 5
Boronia Street (off Centennial Road) Bowral NSW
Fully refundableReserve now, pay when you stay
The price is NZ$266 per night from 12 Apr to 13 Apr
NZ$266
12 Apr - 13 Apr
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
Modern and clean room and bathroom. Staff were friendly and accommodating. Kids loved the indoor heated pool on a cold and rainy day

Reviewed on 10 Mar 2026

Park Proxi Gibraltar Bowral
Berrima Bakehouse Motel

Berrima Bakehouse Motel

3.5 out of 5
19 Old Hume Highway Berrima NSW
The price is NZ$202 per night from 7 Apr to 8 Apr
NZ$202
7 Apr - 8 Apr
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
Central place to stay in Berrima

Reviewed on 17 Mar 2026

Berrima Bakehouse Motel
Berida Hotel

Berida Hotel

4 out of 5
6 David Street Bowral NSW
The price is NZ$314 per night from 24 Mar to 25 Mar
NZ$314
24 Mar - 25 Mar
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
Excellent location, spacious room and comfortable bed. I was on the ground floor opposite the conference room which was being used, it was very noisy especially early in the morning. Limited room service was a bit disappointing but there is a restaurant onsite. Hotel is very dark with a medieval ...

Reviewed on 20 Mar 2026

Berida Hotel
See all 1,605 properties in Southern Highlands
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.

Discover the most popular places to visit in Southern Highlands

Bendooley Estate Book Barn

4.5/5(71 reviews)

Enjoy an outing to Bendooley Estate Book Barn during your stay in Bowral. Amble around this relaxing area's picturesque gardens and enjoy its top-notch restaurants.

Bendooley Estate Book Barn

Centennial Vineyards

4.5/5(39 reviews)

You can enjoy a tasting or tour at Centennial Vineyards during your travels to Bowral. Amble around this relaxing area's picturesque gardens and enjoy its top-notch restaurants.

Centennial Vineyards

Destination Southern Highlands

4.5/5(20 reviews)

Destination Southern Highlands is just one of the places to see in Mittagong, so why not enjoy the other things to explore during your travels? Amble around this relaxing area's picturesque gardens and enjoy its top-notch restaurants.

Destination Southern Highlands

What to do in Southern Highlands

Highland Vines

Personalised wine tour experience in the beautiful NSW Southern Highlands

NZ$291
per adult
Personalised wine tour experience in the beautiful NSW Southern Highlands
Sydney Wine Tasting & Southern Highlands with Pick up & drop off

Sydney Wine Tasting & Southern Highlands with Pick up & drop off

NZ$469
per adult
Sydney Wine Tasting & Southern Highlands with Pick up & drop off
See all activities in Southern Highlands

Frequently asked questions

Can I cancel my flight booking to Southern Highlands due to COVID-19?
Our Customer Service Portal is your one-stop shop for almost every travel question, including about flight cancellations and changes related to COVID-19. For more peace of mind, look over the terms and conditions of your preferred carrier before reserving your tickets.
What's the best way to find cheap flights to Southern Highlands that have flexible change policies?
It's as easy as counting 1-2-3 with Expedia. Step 1: Enter your preferred travel dates and click "Search." Step 2: Check the "No change fee" box underneath the "Flexible change policies" filter on the left-hand side of your screen. Step 3. Reserve your cheap and flexible ticket to Southern Highlands.
What are some of the general tips for travellers to Southern Highlands during the COVID-19 outbreak?
The COVID-19 pandemic has triggered major changes to the way we travel. If you're planning an escape to Southern Highlands, the following tips will help you navigate the "new normal:"
  • Research what, if any, restrictions or rules apply to both your destination and origin. You may not be able to travel depending on local circumstances, so don't forget to check government advisories before booking.
  • When you go through airport checkpoints, keep your face mask on. You will be asked to briefly lower it to verify your identity. Passengers who refuse to wear a mask may face civil penalties and may also be escorted from the building.
  • To reduce the risk of cross-contamination, position your boarding pass on the reader yourself and then hold it up for inspection. Do not hand your pass directly to a TSA agent.
  • You are now allowed to take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on baggage. You'll have to remove it for X-ray screening.
  • Empty your personal items from your pocket, like your keys, phone and wallet, and place them in your carry-on rather than the bins. This will reduce handling during the screening process.
  • Transport your food items in a clear plastic bag and also place them in a screening bin. Keeping your food separate from your carry-on makes it less likely that a TSA agent will need to open your bag for inspection.

Which airlines fly to Southern Highlands?
Secure your airfare with Virgin Australia and then start piecing together your Southern Highlands must-do list. This leading airline has 1976 flights every month to Kingsford Smith Intl. Airport (SYD), a main gateway.
How can I find cheap tickets to Southern Highlands?
In the last seven days, was the best price for a flight to Southern Highlands. If you want to save even more, book well in advance and be flexible with your travel dates. Search for your journey to Southern Highlands, then see prices for nearby days by clicking on our "flexible dates" link.
How much is a flight to Southern Highlands?
There were lots of cheap fares for the taking in the last seven days, with the cost of a return ticket to Southern Highlands varying between and . Many lucky holiday makers locked in one-way seats from () for as little as .
What are the most popular airports to fly into in Southern Highlands?
Book your flight to Kingsford Smith Intl. Airport (SYD) and experience everything that Southern Highlands has to offer. As the region's main point of entry, around 9355 flights land here every month.
When is the cheapest time to fly to Southern Highlands?
If you're not fixed on what day you jet off to Southern Highlands, try to leave early on in the week. The most affordable day to take off is normally Tuesday, closely followed by Monday. Saturday is typically the costliest day, with a lot of people preferring to fly on the weekend.
How much is a plane ticket to Southern Highlands?
In the last seven days, plane fares ranged between and . Scroll through our sensational deals to Southern Highlands, make a booking and get ready for your next fun holiday!
Which airlines with flights to Southern Highlands employ COVID-19 cleanliness policies?
As countries begin to lift travel restrictions, many airlines are now servicing flights with new strategies including social distancing and increased sanitization. Here's what some carriers are doing to ease the spread of COVID-19:
  • Qantas - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Virgin Australia - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Jetstar - this airline is known for providing passenger masks and cleaning with disinfectant.

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