Southern Highlands Vacation Packages

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Your Southern Highlands Vacation

When you're ready to discover someplace new and exciting in the world, satisfy your wanderlust with a customized vacation 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 vacation to the second you come back home, Expedia has your back every step of the way.

Top Southern Highlands Vacation Deals

Price found within the past 48 hours. Click for updated prices.
YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

4 out of 5
Sydney Central Business District
Price was CA $2,934, price is now CA $2,563 per person
CA $2,563
per person
Jun 15 - Jun 20
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Sydney (SYD)
8.2/10 Very Good! (2,699 reviews)
Excellent location, good service. Room was mildly unclean and facilities were fine rather than pristine but for the price and the location we were extremely happy. We could easily access everything circular quay had to offer

Reviewed on May 1, 2026

Huge Harbour View Apartment In Historic Home

Huge Harbour View Apartment In Historic Home

2.5 out of 5
Cremorne
Price was CA $3,493, price is now CA $2,775 per person
CA $2,775
per person
Jun 15 - Jun 20
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Sydney (SYD)
No reviews
Explore Sydney From Stylish North Shore Apartment

Explore Sydney From Stylish North Shore Apartment

2.5 out of 5
Cremorne
Price was CA $3,034, price is now CA $2,571 per person
CA $2,571
per person
Jun 15 - Jun 20
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Sydney (SYD)
No reviews
The Old Clare by Ode Hotels

The Old Clare by Ode Hotels

4.5 out of 5
Chippendale
Price was CA $3,071, price is now CA $2,703 per person
CA $2,703
per person
Jun 15 - Jun 20
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Sydney (SYD)
9.2/10 Wonderful! (566 reviews)
There was absolutely no staff Visibility to help with luggage we had to lug our own luggage to our rooms which is unheard of / previous owners had bell staff to take your luggage from the car - foyer areas are very run down - whole hotel needs a revamp as it’s looking very stayed - it is such a shame as we have been here many times under the old owners and loved it every time - this time we have been left wanting - even the rooftop bar was empty which tells you something - this used to ALwAyS be pumping …. Do better to stay competitive

Reviewed on Feb 28, 2026

Ace Hotel Sydney

Ace Hotel Sydney

5 out of 5
Sydney Central Business District
Price was CA $3,138, price is now CA $2,807 per person
CA $2,807
per person
Jun 15 - Jun 20
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Sydney (SYD)
9.4/10 Exceptional! (908 reviews)
Really impressed with Ace Hotel Sydney. They’ve done a great job capturing that New York feel and bringing it into Sydney without it feeling forced. The location is a big win, right in a cool, lively part of the city with easy access to everything you’d want. Makes it a great base whether you’re here for work or a weekend. Rooms are well designed and stylish, though a little on the smaller side. That said, the bed was seriously comfortable, which more than makes up for it after a long day. Didn’t get a chance to try Kiln, which was a bit of a shame as I’ve heard great things, but gives me a reason to come back. What really stood out was the team, genuinely friendly, helpful, and made the whole stay feel easy. Would definitely stay again.

Reviewed on Apr 29, 2026

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

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Southern Highlands Hotel Deals

The Gibraltar

The Gibraltar

4 out of 5
Boronia Street (off Centennial Road) Bowral NSW
Fully refundableReserve now, pay when you stay
The price is CA $196 per night from May 25 to May 26
CA $196
CA $216 total
May 25 - May 26
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
Location was good, we walked into town for breakfast every day, which took 30 min. We ate at the bar twice, and was happy with the meal.

Reviewed on May 2, 2026

The Gibraltar
Berrima Bakehouse Motel

Berrima Bakehouse Motel

3.5 out of 5
19 Old Hume Highway Berrima NSW
The price is CA $147 per night from May 21 to May 22
CA $147
CA $164 total
May 21 - May 22
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
Beautiful setting by the river and so convenient.

Reviewed on Apr 29, 2026

Berrima Bakehouse Motel
Berida Hotel

Berida Hotel

4 out of 5
6 David Street Bowral NSW
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from May 18 to May 19
CA $208
CA $229 total
May 18 - May 19
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Small room - Pettit Double, but good bed and nice shower. Everything I needed really.

Reviewed on Apr 29, 2026

Berida Hotel
See all 1,624 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.
All Inclusive Vacations
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What to do in Southern Highlands

Highland Vines

Personalised wine tour experience in the beautiful NSW Southern Highlands

CA $240
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

CA $455
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 travelers 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 vacationers 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 vacation!
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.