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.
APX Darling Harbour

APX Darling Harbour

3.5 out of 5
Sydney Central Business District
per person
Oct 9 - Oct 14
found 20 hours ago
Roundtrip flight included
Vancouver (YVR) to Sydney (SYD)
7.6/10 Good! (1,002 reviews)
The street where this motel is located, this is not the fault of APX motel group, it's more to do with the local council and surrounding buildings/restaurants to keep the street to a reasonably clean condition, rental bikes blocking the narrow footpath, cigarette butts all over the place doesn't make for a very appealing welcome to the neighbourhood.

Reviewed on Jul. 20, 2025

InterContinental Sydney Double Bay by IHG

InterContinental Sydney Double Bay by IHG

5 out of 5
Double Bay
per person
Oct 9 - Oct 14
found 20 hours ago
Roundtrip flight included
Vancouver (YVR) to Sydney (SYD)
9/10 Wonderful! (570 reviews)
wonderful get away, five star experience. Breakfast is a must!

Reviewed on Jun. 24, 2025

Coogee Bay Boutique Hotel

Coogee Bay Boutique Hotel

4 out of 5
Coogee
per person
Oct 9 - Oct 14
found 20 hours ago
Roundtrip flight included
Vancouver (YVR) to Sydney (SYD)
8.8/10 Excellent! (820 reviews)
Great facility and location

Reviewed on Jun. 29, 2025

Pullman Quay Grand Sydney Harbour

Pullman Quay Grand Sydney Harbour

5 out of 5
Sydney Central Business District
per person
Sep 23 - Sep 27
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Sydney (SYD)
9.2/10 Wonderful! (1,003 reviews)
It’s right on the quay,

Reviewed on Jul. 21, 2025

Spicers Sangoma Retreat - Adults Only

Spicers Sangoma Retreat - Adults Only

4.5 out of 5
Bowen Mountain
per person
Aug 30 - Sep 4
found 11 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Sydney (SYD)
10/10 Exceptional! (43 reviews)
Quite isolated and rooms getting a bit tired but staff and food great and very relaxing

Reviewed on Feb. 15, 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

Park Proxi Gibraltar Bowral

Park Proxi Gibraltar Bowral

3.5 out of 5
Boronia Street (off Centennial Road), Bowral, NSW
Fully refundableReserve now, pay when you stay
The price is CA $194 per night from Jul 28 to Jul 29
CA $194
CA $214 total
Jul 28 - Jul 29
includes taxes & fees
8.4/10 Very Good! (999 reviews)
Hidden Gems
"Very good experience! Very friendly staff and very yummy breakfast buffet! My wife and kids love the stay very much!"

Reviewed on Jul. 8, 2025

Park Proxi Gibraltar Bowral
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 $124 per night from Jul 22 to Jul 23
CA $124
CA $137 total
Jul 22 - Jul 23
includes taxes & fees
8/10 Very Good! (625 reviews)
"Renovated room and other renovations in progress. Great staff! Good dining and bar facilities on site. Standard room is small, but well renovated, warm and great bed. Overall a very pleasant and affordable stay"

Reviewed on Jul. 7, 2025

The Dormie House - On The Golf Course
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 Jul 27 to Jul 28
CA $138
CA $152 total
Jul 27 - Jul 28
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"We couldn't have asked for more. Everything was catered for, and the comfort and quality of Rosier Cottage easily rivalled many top-tier motels. Great value for money."

Reviewed on Jul. 18, 2025

Berrima Bakehouse Motel
See all 1,611 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

Bradman Oval and Don Bradman Museum & International Cricket Hall of Fame

Guided Don Bradman Cricket Tour From Sydney

CA $224
per adult
Guided Don Bradman Cricket Tour From Sydney
Highland Vines

Personalised wine tour experience in the beautiful NSW Southern Highlands

CA $221
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 $2,225. 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.