Southern Highlands Holidays from AU$514

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Your Southern Highlands Holiday

When you're ready to discover someplace new and exciting in the world, satisfy your wanderlust with a customised holiday package to Southern Highlands. Noted for its rural countryside and spectacular views, it won't be long before you fall for the charms of this destination. Get your trip to Southern Highlands off to a memorable start by making Bowral the first stop. This city is a favourite with visitors from near and far. From the instant you book your Southern Highlands holiday to the second you come back home, Expedia has your back every step of the way.

The Latest Southern Highlands Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Charming Studio Apartment in the Heart of Sydney

Charming Studio Apartment in the Heart of Sydney

2.5 out of 5
Sydney Central Business District
Save 100% on your flight
Price was AU$851, price is now AU$514 per person
AU$514
per person
17 Mar - 20 Mar
found 1 day ago
Return flight included
Melbourne (MEL) to Sydney (SYD)
No reviews
YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

4 out of 5
Sydney Central Business District
Save 100% on your flight
Price was AU$1,790, price is now AU$976 per person
AU$976
per person
1 Apr - 8 Apr
found 1 day ago
Return flight included
Adelaide (ADL) to Sydney (SYD)
8.2/10 Very Good! (2,388 reviews)
Conveniently close to Darling Harbor. Friendly and helpful staff.

Reviewed on 21 Jan 2026

The Ultimo

The Ultimo

4 out of 5
Haymarket
Save 100% on your flight
Price was AU$1,321, price is now AU$724 per person
AU$724
per person
1 Apr - 8 Apr
found 1 day ago
Return flight included
Adelaide (ADL) to Sydney (SYD)
8.8/10 Excellent! (1,000 reviews)
Our stay at The Ultimo was great. Room was clean and comfortable, staff were friendly and the location is superb.

Reviewed on 15 Jan 2026

Bright 3-bed House With Garden,

Bright 3-bed House With Garden,

2.5 out of 5
Save 100% on your flight
Price was AU$2,336, price is now AU$1,321 per person
AU$1,321
per person
11 Mar - 18 Mar
found 1 day ago
Return flight included
Brisbane (BNE) to Sydney (SYD)
No reviews
Chic Urban Paddington Escape

Chic Urban Paddington Escape

2.5 out of 5
Paddington
Save 100% on your flight
Price was AU$872, price is now AU$524 per person
AU$524
per person
17 Mar - 20 Mar
found 1 day ago
Return flight included
Melbourne (MEL) 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
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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

Southern Highlands Essential Information

Language
English
Currency
Australian dollars
Closest Airport
Kingsford Smith Intl. Airport (SYD)
Top Sights
Corbett Gardens, Glow Worm Glen and Leighton Gardens

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 AU$221 per night from 15 Feb to 16 Feb
AU$221
15 Feb - 16 Feb
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
We had an amazing stay. The kids had thr best time at the pool.

Reviewed on 17 Jan 2026

Park Proxi Gibraltar Bowral
The Robertson Hotel

The Robertson Hotel

3.5 out of 5
1 Fountaindale Rd Robertson NSW
The price is AU$140 per night from 28 Jan to 29 Jan
AU$140
28 Jan - 29 Jan
includes taxes & fees
7.8/10 Good! (353 reviews)
The Robertson Hotel is a sanctuary where the raveled sleeve can be knitted up again :) Beautiful surrounds, friendly, attentive staff, lovely breakfast. My only worry is that its gentle, historical charm will be lost in future development. Sydney needs this kind of retreat from its mass tourism ...

Reviewed on 14 Jan 2026

The Robertson Hotel
Berrima Bakehouse Motel

Berrima Bakehouse Motel

3.5 out of 5
19 Old Hume Highway Berrima NSW
The price is AU$165 per night from 27 Jan to 28 Jan
AU$165
27 Jan - 28 Jan
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
Clean & spacious room, great shower and supplies. Bed wasn’t the most comfortable.

Reviewed on 17 Jan 2026

Berrima Bakehouse Motel
See all 1,637 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.
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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 lively bars.

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 lively bars.

Centennial Vineyards

Moss Vale Golf Club

4/5(9 reviews)

Enjoy a round of golf in Bowral at Moss Vale Golf Club. Amble around this relaxing area's picturesque gardens and enjoy its lively bars.

Moss Vale Golf Club

What to do in Southern Highlands

Highland Vines

Personalised wine tour experience in the beautiful NSW Southern Highlands

AU$245
per adult
Personalised wine tour experience in the beautiful NSW Southern Highlands
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.