Southern Highlands Vacations from $1,372
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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 favorite 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.
The Latest Southern Highlands vacation packages
Price found within the past 48 hours. Click for updated prices.
25hours Hotel Sydney The Olympia
Paddington
Price was $1,698, price is now $1,423 per person
$1,423
per person
May 31 - Jun 5
found 20 hours ago
Roundtrip flight included
Los Angeles (LAX) to Sydney (SYD)
9.6/10 Exceptional! (34 reviews)
Perfect location for exploring Sydney. Nice design and good size room. Staff are very friendly. Decent cafe on premise and within easy access of nearby restaurants and bars. Really enjoyed my stay.
Reviewed on Mar 25, 2026
Wildlife Retreat at Taronga
Mosman
Price was $2,176, price is now $1,946 per person
$1,946
per person
Jul 14 - Jul 18
found 20 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sydney (SYD)
9.8/10 Exceptional! (881 reviews)
This was one of the best experiences during our trip to Sydney. Beautiful place and great cause. So worth it!
Reviewed on Apr 17, 2026
Furama Darling Harbour
Haymarket
Price was $1,848, price is now $1,656 per person
$1,656
per person
Jul 14 - Jul 18
found 20 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sydney (SYD)
8.4/10 Very Good! (1,004 reviews)
Brilliant location for accessing Chinatown, shopping options, and the light rail that connects to everything. Disappointed in the room servicing on the weekend but was able to get enough towels to see me through my stay. Will definitely stay there again but please do a better job servicing the rooms.
Reviewed on Apr 8, 2026
Rydges Sydney Airport Hotel
Mascot
Price was $1,860, price is now $1,673 per person
$1,673
per person
Jul 14 - Jul 18
found 20 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sydney (SYD)
8.8/10 Excellent! (3,109 reviews)
Great location - super easy
Reviewed on Apr 21, 2026
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See all available trips from Columbus to Southern Highlands
View all tripsWhere 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 Cecil Hoskins Nature Reserve.
Discover the most popular places to visit in Southern Highlands
Bendooley Estate Book Barn
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.
Centennial Vineyards
5/5(1 review)
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.
Moss Vale Golf Club
Enjoy a round of golf in Bowral at Moss Vale Golf Club. Amble around this quaint area's picturesque gardens and enjoy its lively bars.
What to do in Southern Highlands
Sydney Wine Tasting & Southern Highlands with Pick up & drop off
$326
per adult
Southern Highlands Hotel Deals
The Gibraltar
Boronia Street (off Centennial Road) Bowral NSW
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $158 total per night from May 12 to May 13
$158 total
May 12 - May 13
Total with taxes and fees
8.6/10 Excellent! (1,015 reviews)
Breakfast was a small buffet but everything was delicious. The staff in the restaurant were lovely, however they didn’t mention that everytime we asked for a coffee thinking it was part of the buffet breakfast that there were additional charges. The executive room itself was clean and had a beautiful ...
Reviewed on Apr 20, 2026
Berrima Bakehouse Motel
19 Old Hume Highway Berrima NSW
$110 nightly
The price is $120 total per night from Apr 26 to Apr 27
$120 total
Apr 26 - Apr 27
Total with taxes and fees
9.4/10 Exceptional! (1,014 reviews)
Room was spotless, bright & airy
Reviewed on Apr 19, 2026
Bundanoon Hotel
6-18 Erith Street Bundanoon NSW
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $98 total per night from Apr 22 to Apr 23
$98 total
Apr 22 - Apr 23
Total with taxes and fees
7.6/10 Good! (459 reviews)
The hotel had a lot of character. Very handy and a great restaurant.
Reviewed on Apr 17, 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.
Find the Best Southern Highlands Vacation Packages
Southern Highlands Essential Information
Language | English |
|---|---|
Currency | Australian dollars |
Closest Airport | Kingsford Smith Intl. Airport (SYD) |
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