Southern Highlands Vacation Packages 2025/2026 from $2,172

Southern Highlands flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Citadines Connect Sydney Airport

Mascot

$2,172

per person

Dec 16 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Sydney (SYD)

This hotel features a 24-hour gym and a rooftop terrace. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and airport shuttle. A bar/lounge, a 24-hour front desk, and a coffee shop are also provided.

Ovolo Woolloomooloo

Woolloomooloo

$2,481

per person

Dec 16 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Sydney (SYD)

A marina, a gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.

Rydges Australia Square

Sydney Central Business District

$2,341

per person

Dec 16 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Sydney (SYD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling for business? Take advantage of the free WiFi in public areas, express check-in, and conference space. A coffee shop, a snack bar/deli, and express check-out are also on offer.

The Old Clare by Ode Hotels

Chippendale

$2,412

per person

Dec 16 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Sydney (SYD)

This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Traveling on business? Take advantage of the 3 conference rooms, free WiFi in public areas, and laundry service. There's an outdoor pool on site, and a 24-hour front desk and a coffee shop are also provided.

Rydges World Square

Sydney Central Business District

$2,285

per person

Dec 16 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Sydney (SYD)

A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a snack bar/deli, and express check-in are also offered.

Top Southern Highlands hotels deals

Berrima Bakehouse Motel

19 Old Hume Highway, (entrance via Wingecarribee St), Berrima, NSW

$100 nightly

$110 total

Nov 30 - Dec 1

Total with taxes and fees

Free WiFi in public areas, a garden, and a picnic area are available at this motel. Express check-out and barbecue grills are also provided.

Free WiFi

Air conditioning

Park Proxi Gibraltar Bowral

Boronia Street (off Centennial Road), Bowral, NSW

Free Cancellation

Reserve now, pay when you stay

$144 nightly

$159 total

Nov 6 - Nov 7

Total with taxes and fees

A golf course and a gym are featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy a meal from the a restaurant and perks like free self parking.

Parking included

Free WiFi

Bundanoon Hotel

6-18 Erith Street, Bundanoon, NSW

Free Cancellation

Reserve now, pay when you stay

$81 nightly

$89 total

Nov 6 - Nov 7

Total with taxes and fees

This hotel features a restaurant, an outdoor tennis court, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden is also provided.

Parking included

Free WiFi

Links House

17 Links Road, Burradoo, NSW

$143 nightly

$158 total

Nov 16 - Nov 17

Total with taxes and fees

A restaurant and a bar/lounge are featured at this guesthouse. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A business center, a garden, and a snack bar/deli are also on offer.

Breakfast included

Pet friendly

The Robertson Hotel

1 Fountaindale Rd, Robertson, NSW

$98 nightly

$108 total

Nov 6 - Nov 7

Total with taxes and fees

An outdoor pool is featured at this guesthouse, along with free self parking. WiFi in public areas is free. A garden, a lobby fireplace, and a picnic area are also on offer.

Pool

Parking included

Poplars at Mittagong

97 to 99 Old Hume Highway, Braemar, NSW

Free Cancellation

Reserve now, pay when you stay

$77 nightly

$85 total

Nov 7 - Nov 8

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a picnic area are also on offer.

Parking included

Free WiFi

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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.

Popular places to visit

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 lively bars.

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 lively bars.

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.

Frequently asked questions

How much are vacation packages to Southern Highlands?

Starting as low as $2,172, hotel and flight packages are a superb way to make your budget stretch further. Get ready Southern Highlands — here you come!

Where can I get the best vacation package deals for Southern Highlands?

You'll find amazing Southern Highlands package deals with Travelocity. Pick and choose from 400 partner airlines and 1,000,000 worldwide properties and turn those vacation dreams into reality.

Why should I purchase my Southern Highlands vacation bundle via Travelocity?

We've got 24/7 support, high-quality service and a Price Match Guarantee. Life's a big journey — and we have exciting destinations for you to journey to all around the world. Travel with us and your bank balance will thank you for it.

Can I save money on my Southern Highlands car rental if I combine it with my hotel or flight?

Sure can. And our Southern Highlands vacation packages are the perfect way to do it. With only a few clicks you can save money as well as time by bundling your bookings. Collect the keys to your rental car and feel the freedom of the open road. Searching for things to do? Throw some tours or experiences into your package and make savings on those too.

Which airport is best for Southern Highlands?

Southern Highlands has two major airports — Kingsford Smith Intl. Airport (SYD) and Shellharbour Airport (WOL).

What is there to do in Southern Highlands?

Southern Highlands boasts hidden surprises at every turn, but be sure you get to Bendooley Estate Book Barn and Centennial Vineyards while you're in town. These attractions are popular with visitors.