Southern Highlands Vacation Packages 2026 from $1,593

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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.

YEHS Hotel Sydney Harbour Suites

Sydney Central Business District

$1,593

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip non-stop flight included

Chicago (CHI) to Sydney (SYD)

8.2/10 Very Good! (2,960 reviews)

Medusa Boutique Hotel

Darlinghurst

$3,564

per person

Dec 30 - Jan 4

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Sydney (SYD)

9.6/10 Exceptional! (498 reviews)

Wow, the Medusa is absolutely fabulous! Love the beautifully designed interior which has bags of character and uses gorgeous colours, textures and sumptuous materials to create a feeling of period splendour and true luxury. Staff were fun, friendly and helpful. Evenings on the balcony, shaded by a pretty tree complete with fairylights and the occasional visit from a shy possum, were divine. A truly memorable stay.

Reviewed on Oct 13, 2026

Bondi Studio Apartment With Pool & Rooftop Views

Bondi

$2,529

per person

Jan 6 - Jan 10

found 13 hours ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Sydney (SYD)

No reviews

YEHS Hotel Sydney QVB

Sydney Central Business District

$1,598

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip non-stop flight included

Chicago (CHI) to Sydney (SYD)

8.6/10 Excellent! (1,004 reviews)

Staff was really helpful and it’s in a great location

Reviewed on Oct 18, 2026

Establishment Hotel

Sydney Central Business District

$1,680

per person

Nov 24 - Nov 28

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Sydney (SYD)

9/10 Wonderful! (697 reviews)

Extremely helpful staff. Luxurious experience

Reviewed on Oct 21, 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.

A waterfall cascading down a rocky cliff surrounded by dense green foliage.

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.

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.

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.

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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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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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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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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Harper's Mansion

8.8/10 (23 reviews)

You can learn about the history of Bowral with a trip to Harper's Mansion. 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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What to do in Southern Highlands

Personalised wine tour experience in the beautiful NSW Southern Highlands

$174

per adult

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

$316

per adult

See all activities in Southern Highlands

Southern Highlands Hotel Deals

Berrima Bakehouse Motel

19 Old Hume Highway Berrima NSW

$105 nightly

$116 total

Nov 4 - Nov 5

Total with taxes and fees

9.4/10 Exceptional! (1,004 reviews)

"Peaceful, clean,pretty gardens, close to food, close to bowral and mossvale 10 min drive."

Reviewed on Oct 20, 2026

The Gibraltar

Boronia Street (off Centennial Road) Bowral NSW

Fully refundableReserve now, pay when you stay

$164 nightly

$181 total

Nov 22 - Nov 23

Total with taxes and fees

8.4/10 Very Good! (1,002 reviews)

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Reviewed on Oct 21, 2026

Moss Vale Holiday Park

43/53 Willow Drive Moss Vale NSW

$88 nightly

$88 total

Nov 2 - Nov 3

Total with taxes and fees

8.8/10 Excellent! (83 reviews)

"Very clean and tidy room. One of the nicest beds, and much better than some of hotels I’ve stayed in before."

Reviewed on Oct 20, 2026

See all 1,644 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.