Southern Highlands Vacation Packages 2026 from $1,489

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.

YEHS Hotel Sydney CBD

Sydney Central Business District

$1,489

per person

Dec 5 - Dec 9

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Sydney (SYD)

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

The first room was not the room I reserved, the bed was just a little bigger then a double but I know I reserved a queen. Finally moved to a slightly bigger room but it's still a small room.

Reviewed on Sep 27, 2026

Capella Sydney

Sydney Central Business District

$3,735

per person

Dec 21 - Dec 27

found 1 day ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Sydney (SYD)

9.8/10 Exceptional! (413 reviews)

Attention to detail was amazing. Top service and spacious room.

Reviewed on Sep 6, 2026

Bright Tamarama 2-bed With Balcony Water View

Tamarama

$2,265

per person

Dec 12 - Dec 17

found 7 hours ago

Roundtrip non-stop flight included

San Francisco (SFO) to Sydney (SYD)

No reviews

3-bedroom Home in the Heart of Darlinghurst

Darlinghurst

$2,076

per person

Dec 5 - Dec 9

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Sydney (SYD)

10/10 Exceptional! (1 review)

The York by Swiss-Belhotel International

Sydney Central Business District

$2,869

per person

Nov 3 - Nov 8

found 3 hours ago

Roundtrip non-stop flight included

New York (NYC) to Sydney (SYD)

8.6/10 Excellent! (2,745 reviews)

Great place to stay. Clean, comfortable and friendly staff.

Reviewed on Sep 26, 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

Oct 6 - Oct 7

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 30 - Oct 1

Total with taxes and fees

8.4/10 Very Good! (1,004 reviews)

"From the moment we walked into the Lobby it exuded luxury, The whole Hotel smelled luxurious, the rooms do not disappoint, the pool is fabulous. When it came to Harvey’s bar, the staff were AMAZING, everything was personal, they learned our names, drinks top notch. The food in the restaurant was ..."

Reviewed on Sep 26, 2026

Moss Vale Holiday Park

43/53 Willow Drive Moss Vale NSW

$86 nightly

$86 total

Oct 21 - Oct 22

Total with taxes and fees

8.8/10 Excellent! (77 reviews)

"Quiet, comfortable and dog-friendly."

Reviewed on Sep 26, 2026

See all 1,628 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.