Southern Highlands Vacation Packages 2026 from $1,657

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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 favorite 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.

The Latest Southern Highlands vacation packages

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

Studio3: Chic Bondi Abode With Pool & A/C

Bondi Junction

$1,657

per person

Nov 3 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Sydney (SYD)

No reviews

Pullman Sydney Hyde Park

Darlinghurst

$2,152

per person

Nov 3 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Sydney (SYD)

8.6/10 Excellent! (1,005 reviews)

No outlets around beds

Reviewed on Aug 14, 2026

Nesuto Woolloomooloo Sydney Apartments

Woolloomooloo

$1,735

per person

Nov 3 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Sydney (SYD)

8.6/10 Excellent! (1,001 reviews)

We stayed in room 216 for three nights, it was great! Regina at front desk was awesome, letting us check in earlier after our long flight from the US. Apartments are spacious clean and comfortable, everything you need for a great stay! Close to all the sights if you are happy to walk, Circular Quay, Sydney Habour, Opera House, Botanical Gardens! Coffee place at the end of Dowling St was great! Bus stop close by to get to Bondi. Would stay again if coming back to Sydney!

Reviewed on Jul 29, 2026

The Brighton Hotel Sydney - MGallery Collection

Brighton-le-Sands

$2,218

per person

Nov 3 - Nov 8

found 2 days ago

Roundtrip non-stop flight included

New York (JFK) to Sydney (SYD)

8/10 Very Good! (1,000 reviews)

One of favorite places to stay! The room service food was divine

Reviewed on Aug 11, 2026

Coogee Bay Boutique Hotel

Coogee

$1,862

per person

Nov 3 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Sydney (SYD)

8.8/10 Excellent! (876 reviews)

Was an amazing stay! Travelled round Melbourne and Sydney whilst in Australia and definitely the best hotel we stayed in! Definitely would recommend to others staying in the Coogee/ Bondi area

Reviewed on May 22, 2026

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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

A white picket fence with a sign that reads "ENTRY" and an arrow pointing to the right.

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.

A green field with a mountain range in the background.

Burradoo

Bars, gardens, and golf courses highlight some of the notable features of Burradoo. Make a stop by Cecil Hoskins Nature Reserve while you're exploring.

Mittagong Town Centre

1 out of top 10 points of interest in this area

While Mittagong Town Centre isn't home to many top sights, Destination Southern Highlands and Mount Jellore Lookout are some notable places to visit nearby.

New Berrima

Though New Berrima might not have many top sights, you can venture to the surrounding area to see attractions like Berrima Gaol and Harper's Mansion.

Braemar

The restaurants and gardens are just a few features travelers like about Braemar. If you want to do some sightseeing nearby, Destination Southern Highlands and Artemis Wines are a few top places to visit.

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 top-notch restaurants.

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Centennial Vineyards

9.2/10 (215 reviews)

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.

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Corbett Gardens

8.6/10 (79 reviews)

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.

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Destination Southern Highlands

9.2/10 (115 reviews)

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.

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Southern Highland Wines

8.6/10 (29 reviews)

You can enjoy a tasting or tour at Southern Highland Wines during your travels to Sutton Forest. Amble around this quaint area's picturesque gardens and enjoy its lively bars.

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Bowral Golf Course

8.6/10 (61 reviews)

Enjoy a round of golf in Bowral at Bowral Golf Course. Amble around this relaxing area's picturesque gardens and enjoy its top-notch restaurants.

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Berrima Gaol

8.4/10 (116 reviews)

Learn about the local history of Bowral with a stop at Berrima Gaol. Amble around this relaxing area's picturesque gardens and enjoy its top-notch restaurants.

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Moss Vale Golf Club

8.6/10 (61 reviews)

Enjoy a round of golf in Bowral at Moss Vale Golf Club. Amble around this relaxing area's picturesque gardens and enjoy its lively bars.

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What to do in Southern Highlands

Sydney Wine Tasting & Southern Highlands with Pick up & drop off

$318

per adult

See all activities in Southern Highlands

Southern Highlands Hotel Deals

Berrima Bakehouse Motel

19 Old Hume Highway Berrima NSW

$108 nightly

$119 total

Aug 18 - Aug 19

Total with taxes and fees

9.4/10 Exceptional! (1,001 reviews)

"Absolutely gorgeous grounds. Clean and comfortable rooms. Effortless check-in and out. Would highly recommend."

Reviewed on Aug 16, 2026

The Gibraltar

Boronia Street (off Centennial Road) Bowral NSW

Fully refundableReserve now, pay when you stay

$171 nightly

$188 total

Aug 20 - Aug 21

Total with taxes and fees

Peppers Craigieburn

Centennial Road Bowral NSW

Fully refundableReserve now, pay when you stay

$167 nightly

$183 total

Sep 6 - Sep 7

Total with taxes and fees

See all 1,643 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.