Southern Highlands Vacation Packages 2026 from $1,478

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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

$1,478

per person

Nov 20 - Nov 25

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Sydney (SYD)

8.2/10 Very Good! (2,945 reviews)

Establishment Hotel

Sydney Central Business District

$1,609

per person

Nov 21 - Nov 25

found 10 hours ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Sydney (SYD)

9/10 Wonderful! (697 reviews)

We were welcomed by Emily at Front of House who was so helpful. She gave us great recommendations and really made us welcome. My only disappointment was due to booking through Expedia only 1 breakfast was included whereas if we had booked direct both guests would receive breakfast. Otherwise the stay was ideal. The area is great, 10 minute walk to most places, circular quay, the rocks, old sydney, the shopping area in Pitt Street.

Reviewed on Sep 7, 2026

YEHS Hotel Sydney CBD

Sydney Central Business District

$1,692

per person

Dec 6 - Dec 13

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) 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

Bright Tamarama 2-bed With Balcony Water View

Tamarama

$2,265

per person

Dec 12 - Dec 17

found 1 day ago

Roundtrip non-stop flight included

San Francisco (SFO) to Sydney (SYD)

No reviews

Delightful 4-bed Home Near Centennial Park

Queens Park

$2,245

per person

Dec 14 - Dec 17

found 23 hours ago

Roundtrip flight included

San Francisco (SFO) to Sydney (SYD)

No reviews

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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

The Gibraltar

Boronia Street (off Centennial Road) Bowral NSW

Fully refundableReserve now, pay when you stay

$169 nightly

$186 total

Oct 6 - Oct 7

Total with taxes and fees

8.4/10 Very Good! (1,005 reviews)

"The staff were very welcoming and accommodating with our needs. The only negative is the food from the bar, took a long time and the standard was not very good. However, our meal was refunded due to the wait and standard. Would stay again as very relaxing"

Reviewed on Sep 29, 2026

Moss Vale Holiday Park

43/53 Willow Drive Moss Vale NSW

$86 nightly

$86 total

Oct 26 - Oct 27

Total with taxes and fees

8.8/10 Excellent! (78 reviews)

"Lovely to have received lots of contact regarding arrival as I thought I would arrive after hours. Lovely greeting when I did arrive. Basic cabin for solo traveler. Very clean. Pleasantly surprised how comfortable the bed was. The shower was great and everything I needed was in the very dated cabin. ..."

Reviewed on Sep 29, 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.