Southern Highlands Vacation Packages 2025 from $1,473

Southern Highlands flight + hotel vacation packages

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

Novotel Sydney Darling Square

Sydney Central Business District

per person

Aug 9 - Aug 11

found 4 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Sydney (SYD)

This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. There's a bar/lounge on site, and a 24-hour front desk and wedding services are also provided.

Kozyguru | Barangaroo | Waterfront Views Studio

Sydney Central Business District

per person

Aug 9 - Aug 11

found 4 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Sydney (SYD)

The Albert Hotel Mosman

Mosman

per person

Jul 25 - Jul 28

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Sydney (SYD)

A bar/lounge and a terrace are featured at this hotel, along with self parking. WiFi in public areas is free. Express check-in, express check-out, and luggage storage are also on offer.

Rendezvous Hotel Sydney The Rocks

The Rocks

per person

Jul 25 - Jul 28

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Sydney (SYD)

This aparthotel features an outdoor pool and a gym. Self parking, WiFi in public areas, and express check-out are also offered.

Metawise 2BR Apartment in Heart of Hurlstone Park

Hurlstone Park

per person

Jul 25 - Jul 28

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Sydney (SYD)

Free WiFi in public areas is available at this apartment. Take advantage of the free self parking.

Top Southern Highlands hotels deals

Park Proxi Gibraltar Bowral

Boronia Street (off Centennial Road), Bowral, NSW

Free Cancellation

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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

Berida Hotel

6 David Street, Bowral, NSW

Free Cancellation

Reserve now, pay when you stay

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This guesthouse features a restaurant and 2 bars/lounges. Enjoy the 24-hour gym and perks like free self parking and free WiFi. A terrace, a garden, and a snack bar/deli are also on offer.

Parking included

Free WiFi

Peppers Craigieburn

Centennial Road, Bowral, NSW

Free Cancellation

Reserve now, pay when you stay

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A golf course and a restaurant are featured at this smoke-free hotel. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. A coffee shop, a terrace, and a garden are also on offer.

Pet friendly

Parking included

The Dormie House - On The Golf Course

Arthur Street, Moss Vale, NSW

Free Cancellation

Reserve now, pay when you stay

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A golf course and a restaurant are featured at this smoke-free bed & breakfast. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. A terrace, a garden, and a snack bar/deli are also on offer.

Parking included

Free WiFi

Berrima Bakehouse Motel

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

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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

The Robertson Hotel

1 Fountaindale Rd, Robertson, NSW

Free Cancellation

Reserve now, pay when you stay

Get rates

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

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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

5/5(1 review)

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.

Destination Southern Highlands

Destination Southern Highlands is just one of the places to see in Mittagong, so why not enjoy the other things to explore during your travels? Amble around this relaxing area's picturesque gardens and enjoy its top-notch restaurants.

Frequently asked questions

How much are vacation packages to Southern Highlands?

Starting as low as $1,473, 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.