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 $2,841, price is now CA $2,417 per person
CA $2,417
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Sydney (SYD)
8.2/10 Very Good! (2,225 reviews)
Perfect location. Convenient walking distance to public transport, attractions, supermarkets and cafes. The room is generously spacious and equipped with a kitchenette, which allows one to have a proper breakfast in the room, and even dinner. A value for money stunner.

Reviewed on Aug. 19, 2025

YEHS Hotel Sydney CBD

YEHS Hotel Sydney CBD

3.5 out of 5
Sydney Central Business District
Price was CA $3,480, price is now CA $2,718 per person
CA $2,718
per person
Sep 29 - Oct 4
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Sydney (SYD)
8.2/10 Very Good! (1,000 reviews)
Small room, good for short stay, reasonable walk to L2/3 on George St.

Reviewed on Aug. 20, 2025

Ovolo Woolloomooloo

Ovolo Woolloomooloo

5 out of 5
Woolloomooloo
Price was CA $3,459, price is now CA $2,866 per person
CA $2,866
per person
Nov 12 - Nov 17
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Sydney (SYD)
9.2/10 Wonderful! (1,004 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

InterContinental Sydney Double Bay by IHG

InterContinental Sydney Double Bay by IHG

5 out of 5
Double Bay
Price was CA $3,094, price is now CA $2,577 per person
CA $2,577
per person
Nov 12 - Nov 17
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Sydney (SYD)
9/10 Wonderful! (581 reviews)
Loved every little details that was included in our stay. We also came for their winter dome dining experience and we were well taken care of. I would love to come back and enjoy their rooftop pool.

Reviewed on Aug. 16, 2025

Rydges Sydney Airport Hotel

Rydges Sydney Airport Hotel

4 out of 5
Mascot
Price was CA $3,010, price is now CA $2,587 per person
CA $2,587
per person
Nov 12 - Nov 17
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Sydney (SYD)
8.8/10 Excellent! (2,879 reviews)
Excellent accommodation, just walk across the road to the airport. Room was well set out, clean and quiet.

Reviewed on Aug. 20, 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
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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

Berrima Bakehouse Motel

Berrima Bakehouse Motel

3.5 out of 5
19 Old Hume Highway, (entrance via Wingecarribee St), Berrima, NSW
The price is CA $138 per night from Aug 24 to Aug 25
CA $138
CA $152 total
Aug 24 - Aug 25
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"Excellent motel and the room was spacious with a table and chairs. Best motel that I have been to"

Reviewed on Aug. 18, 2025

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 $187 per night from Aug 26 to Aug 27
CA $187
CA $206 total
Aug 26 - Aug 27
includes taxes & fees
8.8/10 Excellent! (725 reviews)
"Staff were excellent especially Michael, room was comfortable and warm. Ethos restaurant was exceptional and my partner and i will be back again😀"

Reviewed on Aug. 17, 2025

Links House
The Dormie House - On The Golf Course

The Dormie House - On The Golf Course

3.5 out of 5
Arthur Street, Moss Vale, NSW
Fully refundableReserve now, pay when you stay
The price is CA $123 per night from Aug 25 to Aug 26
CA $123
CA $136 total
Aug 25 - Aug 26
includes taxes & fees
8/10 Very Good! (632 reviews)
"Rooms nicely refurbished and comfortable"

Reviewed on Aug. 19, 2025

The Dormie House - On The Golf Course
See all 1,588 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
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

What to do in Southern Highlands

Highland Vines

Personalised wine tour experience in the beautiful NSW Southern Highlands

CA $220
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 $2,417. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.