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.
Coastal 2-bed Apartment Near Beach
Dee Why
Price was CA $3,306, price is now CA $2,891 per person
CA $2,891
per person
Dec 9 - Dec 12
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Sydney (SYD)
8/10 Very good! (1 review)
pROPERTY QUALITY WAS VERY GOOD
KEY COULD NOT BE ACCESSED ON ARRIVAL....WAITING IN COLD
aGENT DID NOT RESPOND TO CORRESPONDENCE RE QUERIES ON PROPERTY
Reviewed on Jun 17, 2026
YEHS Hotel Sydney CBD
Sydney Central Business District
Price was CA $4,910, price is now CA $4,232 per person
CA $4,232
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Sydney (SYD)
8.2/10 Very good! (1,005 reviews)
Stayed one night and was perfect for attending an event at Tik Tok Stadium. Close to George Street, which in turn was close to shopping and food places.
Reviewed on Nov 1, 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
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.
Southern Highlands Hotel Deals
Berrima Bakehouse Motel
19 Old Hume Highway Berrima NSW
The price is CA $147 per night from Nov 6 to Nov 7
CA $147
CA $162 total
Nov 6 - Nov 7
includes taxes & fees
The Gibraltar
Boronia Street (off Centennial Road) Bowral NSW
Fully refundableReserve now, pay when you stay
The price is CA $241 per night from Nov 2 to Nov 3
CA $241
CA $265 total
Nov 2 - Nov 3
includes taxes & fees
8.4/10 Very good! (1,000 reviews)
"Very comfortable stay. Friendly staff."
Reviewed on Oct 26, 2026
Moss Vale Holiday Park
43/53 Willow Drive Moss Vale NSW
The price is CA $122 per night from Nov 22 to Nov 23
CA $122
CA $122 total
Nov 22 - Nov 23
includes taxes & fees
8.8/10 Excellent! (86 reviews)
"Quite clean and comfortable very helpful will come back"
Reviewed on Oct 31, 2026
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.
Stay near popular Southern Highlands attractions
What to do in Southern Highlands
Personalised wine tour experience in the beautiful NSW Southern Highlands
CA $241
per adult
Sydney Wine Tasting & Southern Highlands with Pick up & drop off
CA $447
per adult
Frequently asked questions
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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.
