Southern Highlands Vacation Packages 2026 from $2,825

Southern Highlands flight + hotel vacation packages

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

ibis budget Enfield

Strathfield South

$2,825

per person

Dec 30 - Jan 5

found 16 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Sydney (SYD)

This hotel includes free WiFi in public areas and laundry facilities. Take advantage of the self parking.

Quest Bella Vista

Bella Vista

$2,891

per person

Dec 30 - Jan 5

found 16 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Sydney (SYD)

This aparthotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a garden are also offered.

ibis budget Sydney Olympic Park

Sydney Olympic Park

$2,866

per person

Dec 30 - Jan 5

found 16 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Sydney (SYD)

A restaurant, self parking, and a 24-hour front desk are among this hotel's amenities. WiFi in public areas is free. A snack bar/deli, dry cleaning, and luggage storage are also on offer.

Oaks Sydney Goldsbrough Suites

Pyrmont

$3,399

per person

Dec 30 - Jan 5

found 16 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Sydney (SYD)

This aparthotel features an indoor pool and a gym. Enjoy the hot tub and perks like free WiFi. Enjoy the sauna and conveniences like a 24-hour front desk and laundry facilities.

Lakeside Hotel and Conference Centre

Macquarie Park

$3,181

per person

Dec 30 - Jan 5

found 16 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Sydney (SYD)

A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy free perks like free self parking and an area shuttle.

Top Southern Highlands hotels deals

Berrima Bakehouse Motel

19 Old Hume Highway Berrima NSW

$105 nightly

$116 total

Nov 2 - Nov 3

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

The Gibraltar

Boronia Street (off Centennial Road) Bowral NSW

Free Cancellation

Reserve now, pay when you stay

$172 nightly

$189 total

Nov 1 - Nov 2

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

Moss Vale Holiday Park

43/53 Willow Drive Moss Vale NSW

$87 nightly

$87 total

Nov 22 - Nov 23

Total with taxes and fees

This holiday park featured laundry facilities and barbecue grills. Take advantage of the free self parking.

Pet friendly

Parking included

Peppers Craigieburn

Centennial Road Bowral NSW

Free Cancellation

Reserve now, pay when you stay

$124 nightly

$137 total

Nov 16 - Nov 17

Total with taxes and fees

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

Argyle Hotel Southern Highlands

481 Argyle Street Moss Vale NSW

$66 nightly

$72 total

Nov 11 - Nov 12

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. Business travelers can take advantage of the free WiFi in public areas. Free self parking and a terrace are also offered on site.

Parking included

Free WiFi

Berida Hotel

6 David Street Bowral NSW

$152 nightly

$167 total

Nov 23 - Nov 24

Total with taxes and fees

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

Don't see what you're looking for?

See all available properties in Southern Highlands

View all properties

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.

Stay near popular Southern Highlands attractions

Bendooley Estate Book Barn

9.4/10 (334 reviews)

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.

See properties

Frequently asked questions

How much are vacation packages to Southern Highlands?

Starting as low as $2,825, 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.