Southern Highlands Holidays from NZ$1,095

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The Latest Southern Highlands Holiday Deals

Price found within the past 48 hours. Click for updated prices.
YEHS Hotel Sydney CBD

YEHS Hotel Sydney CBD

3.5 out of 5
Sydney Central Business District
per person
24 Oct - 27 Oct
found 10 hours ago
Return flight included
Auckland (AKL) to Sydney (SYD)
8.2/10 Very Good! (1,003 reviews)
Within walking distance to city transport. I had the standard single room which is quite small but adequate for 1 night.

Reviewed on 3 Aug. 2025

YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

4 out of 5
Sydney Central Business District
Save 100% on your flight
per person
21 Oct - 26 Oct
found 1 day ago
Return flight included
Auckland (AKL) to Sydney (SYD)
8.2/10 Very Good! (2,195 reviews)
The front desk staff is very friendly and helpful. Very convenient and perfect location. Close to shopping Center and Chinatown. Surrounded by so many good restaurants. The only downside is our room is quite noisy and cant sleep specially during heavy traffic. I wish they have double glass windows to cut the traffic noise. On our second day the cleaner didn’t empty the rubbish and wash all the cups and mugs. Apart from that all good.

Reviewed on 4 Aug. 2025

Ovolo Woolloomooloo

Ovolo Woolloomooloo

5 out of 5
Woolloomooloo
Save 100% on your flight
per person
21 Oct - 26 Oct
found 1 day ago
Return flight included
Christchurch (CHC) to Sydney (SYD)
9.4/10 Exceptional! (1,007 reviews)
Really quirky hotel with friendly staff, good location, clean, comfortable and sizeable room

Reviewed on 28 Jul. 2025

Rydges Sydney Central

Rydges Sydney Central

4.5 out of 5
Surry Hills
per person
25 Sept - 30 Sept
found 1 day ago
Return flight included
Auckland (AKL) to Sydney (SYD)
8.6/10 Excellent! (1,020 reviews)
Room was clean and comfortable, the restaurant was nice and had good breakfast options. Staff were very friendly. Pool and hot tub were clean and quiet

Reviewed on 2 Aug. 2025

Rydges World Square

Rydges World Square

4.5 out of 5
Sydney Central Business District
per person
21 Oct - 26 Oct
found 1 day ago
Return flight included
Auckland (AKL) to Sydney (SYD)
8.8/10 Excellent! (1,200 reviews)
Thank you, Lili, for your outstanding treatment and service.

Reviewed on 3 Aug. 2025

Our guide on 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

Southern Highlands Holiday

Our pick of the best 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 NZ$186 per night from 13 Aug to 14 Aug
NZ$186
13 Aug - 14 Aug
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Was much better than the photos show. Very nice rooms, great location. Could do with a selection of different pillows as they weren't comfortable."

Reviewed on 31 Jul. 2025

Berrima Bakehouse Motel
Park Proxi Gibraltar Bowral

Park Proxi Gibraltar Bowral

3.5 out of 5
Boronia Street (off Centennial Road), Bowral, NSW
The price is NZ$245 per night from 3 Sept to 4 Sept
NZ$245
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (999 reviews)
"Comfy bed and great restaurant"

Reviewed on 30 Jul. 2025

Park Proxi Gibraltar Bowral
Links House

Links House

4 out of 5
17 Links Road, Burradoo, NSW
Fully refundableReserve now, pay when you stay
The price is NZ$232 per night from 13 Aug to 14 Aug
NZ$232
13 Aug - 14 Aug
includes taxes & fees
8.8/10 Excellent! (719 reviews)
"We enjoyed our stay at the Links House. The room was very clean and comfortable, and the breakfast was delicious."

Reviewed on 18 Jul. 2025

Links House
See all 1,605 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.

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.

Bendooley Estate Book Barn

Centennial Vineyards

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 top-notch restaurants.

Centennial Vineyards

Corbett Gardens

After visiting Corbett Gardens, make a plan to see the other sights and activities in Bowral. Amble around this relaxing area's picturesque gardens and enjoy its lively bars.

Corbett Gardens

What to do in Southern Highlands

Highland Vines

Personalised wine tour experience in the beautiful NSW Southern Highlands

NZ$267
per adult
Personalised wine tour experience in the beautiful NSW Southern Highlands
Bradman Oval and Don Bradman Museum & International Cricket Hall of Fame

Guided Don Bradman Cricket Tour From Sydney

NZ$272
per adult
Guided Don Bradman Cricket Tour From Sydney
See all activities in Southern Highlands

Frequently asked questions

How much does a Southern Highlands holiday package cost?
Get your credit card ready, because a getaway to Southern Highlands starts from an affordable NZ$1,095. When you bundle your flights, hotels and car rentals into a holiday package, you'll score great deals.
How do I get a cheap travel package to Southern Highlands?
Booking a Southern Highlands holiday 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 travellers.
How far in advance should I book my Southern Highlands holiday?
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 holiday 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 holiday package is the most convenient way to organise 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 holiday 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 holiday 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 holiday 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.