Southern Highlands Vacation Packages 2026 from $1,416

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.

Stylish Inner City 2-bed Unit by Fig Lane Park

Ultimo

$1,416

per person

Nov 5 - Nov 8

found 1 day ago

Roundtrip flight included

Los Angeles (QLA) to Sydney (SYD)

No reviews

YEHS Hotel Sydney CBD

Sydney Central Business District

$1,561

per person

Dec 6 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Los Angeles (QLA) to Sydney (SYD)

8.4/10 Very Good! (1,000 reviews)

Room had been renovated. No natural light. Close to cbd

Reviewed on Sep 24, 2026

Bronte Beach Coastal Apartment With Ocean View

Waverley

$1,669

per person

Dec 6 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Los Angeles (QLA) to Sydney (SYD)

No reviews

YEHS Hotel Sydney Harbour Suites

Sydney Central Business District

$1,778

per person

Nov 27 - Dec 2

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Sydney (SYD)

8.2/10 Very Good! (2,903 reviews)

Great hotel for a short stay in Sydney. Perfect location and good facilities

Reviewed on Sep 25, 2026

YEHS Hotel Sydney QVB

Sydney Central Business District

$1,810

per person

Nov 27 - Dec 2

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Sydney (SYD)

8.6/10 Excellent! (1,004 reviews)

Great location, small lobby area and only one single elevator, but overall that was not a problem at all. The room was basic but had everything required - would have been comfortable for two people even though I was travelling solo on this occasion.

Reviewed on Sep 24, 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 Cecil Hoskins Nature Reserve.

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 Artemis Wines are some notable places to visit nearby.

A canyon with steep cliffs and dense forest.

Renwick

Though Renwick might not have many top sights, you can venture to the surrounding area to see attractions like Destination Southern Highlands and Artemis Wines.

A waterfall cascading down a steep cliff surrounded by dense forest.

Welby

Though Welby might not have many top sights, you can venture to the surrounding area to see attractions like Artemis Wines and Destination Southern Highlands.

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.

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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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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 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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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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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 lively bars.

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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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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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What to do in Southern Highlands

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

$324

per adult

See all activities in Southern Highlands

Southern Highlands Hotel Deals

Berrima Bakehouse Motel

19 Old Hume Highway Berrima NSW

$107 nightly

$118 total

Sep 28 - Sep 29

Total with taxes and fees

9.4/10 Exceptional! (1,004 reviews)

"Nice and prompt with room code at 2pm or if you require a early check in can be arranged. Lovely welcome beautiful gardens and car spot's clearly visible. Enjoyed my stay will encourage family and friends to stay too, will return again easy walk to nearby cafe's and place's of interest you can sit ..."

Reviewed on Sep 24, 2026

The Gibraltar

Boronia Street (off Centennial Road) Bowral NSW

Fully refundableReserve now, pay when you stay

$169 nightly

$186 total

Sep 27 - Sep 28

Total with taxes and fees

8.4/10 Very Good! (1,003 reviews)

"We had a wonderful stay at Gibraltar Bowral. The people were very friendly and welcoming, and there was plenty of parking, which was very convenient. The beautiful heated swimming pool was a highlight, and the kids absolutely loved it! The food was very nice, and the whole environment was peaceful, ..."

Reviewed on Sep 24, 2026

Moss Vale Holiday Park

43/53 Willow Drive Moss Vale NSW

$95 nightly

$95 total

Oct 12 - Oct 13

Total with taxes and fees

8.8/10 Excellent! (76 reviews)

"Enjoyed our stay. Would recommend for a night or two if in the area exploring the Southern Highlands"

Reviewed on Sep 20, 2026

See all 1,604 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.