
Southern Highlands Vacations from ¥141,003
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to ¥45,448 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
The Latest Southern Highlands Vacation Packages
Price found within the past 48 hours. Click for updated prices.

YEHS Hotel Sydney Harbour Suites
Sydney Central Business District
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Sydney (SYD)
8.2/10 Very Good! (2,207 reviews)
Excellent location, just few mins walk to QVB, Townhall & Darling Harbour, lots of restaurants nearby.
The room is a bit old, the towel rack had dropped in the washroom.
Dun expect the kitchen could be used as the pot & pan are rusty & other food wares are also dirty so I didn’t cook.
It’s still good value for money considered the location & room size.
Reviewed on Aug 10, 2025


Ovolo Woolloomooloo
Woolloomooloo
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Sydney (SYD)
9.4/10 Exceptional! (1,003 reviews)
The hotel was beautiful, but the common areas were open to the outside and cold. Lovely room, but the water pressure in the shower was very low. No free upgrade was offered. I was told one free bottle of wine per night with my VIP status. But I was given one cheap bottle of wine the first night and that was it - the wine was of such poor quality we did not ask for more. The staff was friendly and professional.
Reviewed on Aug 10, 2025

Sydney Harbour Hotel
The Rocks
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Sydney (SYD)
8.4/10 Very Good! (1,736 reviews)
An unexpected surprise when we arrived at the Sydney airport and immediately took the train to our hotel destination. Easy and close walk to hotel. Another surprise was the ship terminal was right across the street. A short walk later, the Sydney Opera House, shops and restaurants. Great location and convenient.
Reviewed on Aug 13, 2025

Furama Darling Harbour
Haymarket
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Sydney (SYD)
8.4/10 Very Good! (1,001 reviews)
Had a staycation in city with my kids and we loved the convenient of the hotel location. Friday night market and Sat we walked around for kids to play and eat.
Reviewed on Jul 22, 2025
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.
Find the Best Southern Highlands Vacation Packages
Southern Highlands Hotel Deals

Berrima Bakehouse Motel
19 Old Hume Highway, (entrance via Wingecarribee St), Berrima, NSW
The price is ¥14,913 per night from Aug 18 to Aug 19
¥14,913
¥16,404 total
Aug 18 - Aug 19
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"On a quick visit from Canberra, this was a great place to stay. Contactless check-in and check-out, good amenities, clean and tidy and quiet. Would happily stay here again!!"
Reviewed on Aug 10, 2025

Park Proxi Gibraltar Bowral
Boronia Street (off Centennial Road), Bowral, NSW
Fully refundableReserve now, pay when you stay
The price is ¥19,658 per night from Sep 3 to Sep 4
¥19,658
¥21,624 total
Sep 3 - Sep 4
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
"I loved our stay at Park Proxi. It worked for our family even though we aren't golfers. The room was spacious. Our toddler could walk"
Reviewed on Aug 13, 2025

Links House
17 Links Road, Burradoo, NSW
The price is ¥18,295 per night from Aug 25 to Aug 26
¥18,295
¥20,374 total
Aug 25 - Aug 26
includes taxes & fees
8.8/10 Excellent! (721 reviews)
"Enjoyed our stay, friendly staff and the breakfast was excellent"
Reviewed on Aug 8, 2025
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.
What to do in Southern Highlands

Guided Don Bradman Cricket Tour From Sydney
¥24,146
per adult
Frequently asked questions
Other vacations you might like
Expedia's Latest Trends
Hotels
Flights
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.