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.
Bright Tamarama 2-bed With Balcony Water View

Bright Tamarama 2-bed With Balcony Water View

2.5 out of 5
Tamarama
Price was CA $2,864, price is now CA $2,221 per person
CA $2,221
per person
Aug 19 - Aug 24
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Sydney (SYD)
No reviews

YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

4 out of 5
Sydney Central Business District
Price was CA $2,696, price is now CA $2,300 per person
CA $2,300
per person
Aug 15 - Aug 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Sydney (SYD)
8.2/10 Very good! (2,811 reviews)
Spacious room, clean amenities, and friendly staff, all made my trip relaxing and memorable!

Reviewed on Jul 13, 2026

Spicers Potts Point

Spicers Potts Point

4.5 out of 5
Potts Point
Price was CA $2,750, price is now CA $2,484 per person
CA $2,484
per person
Aug 19 - Aug 24
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Sydney (SYD)
9.8/10 Exceptional! (155 reviews)
Class all the way and Phillip at reception was brilliant. The advice he gave regarding local restaurants was well received and accurate. The only disappointment was we had only one night there! We will be back!

Reviewed on Jun 8, 2026

The Langham, Sydney

The Langham, Sydney

5 out of 5
Millers Point
Price was CA $10,505, price is now CA $9,532 per person
CA $9,532
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Sydney (SYD)
9.6/10 Exceptional! (999 reviews)
The service at this Hotel is always first class!

Reviewed on Jul 12, 2026

Pullman Quay Grand Sydney Harbour

Pullman Quay Grand Sydney Harbour

5 out of 5
Sydney Central Business District
Price was CA $10,567, price is now CA $9,623 per person
CA $9,623
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Sydney (SYD)
9.2/10 Wonderful! (1,002 reviews)
Excellent staff.

Reviewed on Jul 2, 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
A white picket fence with a sign that reads "ENTRY" and an arrow pointing to the right.

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.

Find hotels in Moss Vale

Ready to book your vacation to Southern Highlands?

 

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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 $236 per night from Jul 23 to Jul 24
CA $236
CA $259 total
Jul 23 - Jul 24
includes taxes & fees
8.4/10 Very good! (1,004 reviews)
"Amazing experience. Staffs tried their best for what we asked, clean room and beautiful view. Dinner at Marilo restaurant was also satisfying. Would love to go back."

Reviewed on Jul 9, 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 Jul 27 to Jul 28
CA $147
CA $164 total
Jul 27 - Jul 28
includes taxes & fees
9.4/10 Exceptional! (1,007 reviews)
"Clean , warm and comfortable, excellent location"

Reviewed on Jul 13, 2026

Berrima Bakehouse Motel
Links House

Links House

4 out of 5
17 Links Road Burradoo NSW
Fully refundableReserve now, pay when you stay
The price is CA $205 per night from Aug 4 to Aug 5
CA $205
CA $227 total
Aug 4 - Aug 5
includes taxes & fees
9/10 Wonderful! (794 reviews)
"Links house has a very cosy vibe. The restaurant dining was superb and the complimentary breakfast was a lovely added bonus. Staff were very friendly and attentive. Thoroughly enjoyed our stay there."

Reviewed on Jul 12, 2026

Links House
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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Stay near popular Southern Highlands attractions

Bendooley Estate Book Barn

9.4/10 (334 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.
See properties

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
See all activities in Southern Highlands

Frequently asked questions

How much does a Southern Highlands vacation package cost?
Get your credit card ready, because a getaway to Southern Highlands starts from an affordable CA $2,221. When you bundle your flights, hotels and car rentals into a vacation package, you'll score great deals.
How do I get a cheap travel package to Southern Highlands?
Booking a Southern Highlands vacation package with Expedia is one of the easiest ways to save. We offer access to over 550 airlines and 1,000,000 properties across the globe. With such a fabulous range to pick from, you'll have no trouble creating your dream trip.
What are the top hotels in Southern Highlands?
Briars Country Lodge and Berida Hotel know how to make their guests feel at home in Bowral. If your itinerary also includes Mittagong, look up Mittagong Motel and Cabin - Mittagong Caravan Park. Both are popular with travelers.
How far in advance should I book my Southern Highlands vacation?
Earlier is always better. Airlines usually advertise flights up to a year prior to departure, and this is a great opportunity to land some rock-bottom prices. Boss just told you to use up some vacation time next month? No need to worry. Expedia are never short of fantastic deals to help you have the getaway of your dreams, at a price you can afford.
What does an Expedia Southern Highlands travel package include?
Much of that depends on you. You can choose from a variety of Southern Highlands packages, such as a flight, rental car and hotel. You can also book a flight with a hotel, or a flight and a rental car. Once you've made your booking, you can add on the fun stuff like activities and experiences. Whatever your perfect Southern Highlands break looks like, get set to save!
What should I know before booking a Southern Highlands travel package?
Bundling your bookings into a Southern Highlands vacation package is the most convenient way to organize your trip. Not only that, you'll save just for combining your hotels, flights and car rentals. Once you've booked, why not add on a day tour or an activity?
Can I choose my airline with a Southern Highlands Expedia vacation package?
You can, and with more than 550 airlines to select from globally, you're not short on choice. Take a look at the available options and find out which airline fits your needs and budget.
If I'm not able to travel, can I cancel my Southern Highlands vacation package?
Yes you can, and we'll help you every step of the way. You may be able to change or cancel your Southern Highlands vacation package at no cost within 24 hours of booking. But you may incur a fee from your hotel, airline or car rental company if your booking is older than that. If life throws you a curveball, visit our Customer Service Portal for further information.

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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.