Southern Highlands Vacation Packages 2026 from $1,556

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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 QVB

Sydney Central Business District

$1,556

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Sydney (SYD)

8.6/10 Excellent! (1,004 reviews)

Staff was excellent

Reviewed on Sep 15, 2026

YEHS Hotel Sydney Harbour Suites

Sydney Central Business District

$1,815

per person

Nov 26 - Nov 30

found 9 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Sydney (SYD)

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

Complaint already in n hand with Expedia.

Reviewed on Sep 17, 2026

Establishment Hotel

Sydney Central Business District

$1,731

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Sydney (SYD)

9/10 Wonderful! (696 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

Furama Darling Harbour

Haymarket

$1,683

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Sydney (SYD)

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

Great place to stay.very convientant location

Reviewed on Sep 15, 2026

Sofitel Sydney Darling Harbour

Sydney Central Business District

$2,191

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Sydney (SYD)

9/10 Wonderful! (1,003 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 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 Artemis Wines 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.

Beautiful flowing River in Fitzroy water Falls in Bowral NSW Australia beautiful colourful cloudy skies lovely waterfalls

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.

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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Santi Forest Monastery

6.8/10 (10 reviews)

You can find out about the history of Bundanoon with a trip to Santi Forest Monastery. Wander around the gardens in this relaxing area, or simply enjoy its bars.

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What to do in Southern Highlands

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

$325

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

Sep 21 - Sep 22

Total with taxes and fees

9.4/10 Exceptional! (1,001 reviews)

"We booked 3 rooms for a special weekend celebration. The rooms were very clean & comfortable. We had a great time."

Reviewed on Sep 18, 2026

The Gibraltar

Boronia Street (off Centennial Road) Bowral NSW

Fully refundableReserve now, pay when you stay

$171 nightly

$188 total

Sep 21 - Sep 22

Total with taxes and fees

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

"Okay stay only. Good location not too far from Bowral. Views were really nice... Mt Gibraltar and golf course. We enjoyed dinner and a drink in the bar by the fire. However.. hotel was *very* quiet, very few rooms were occupied and yet we were given room 214 which we have learned shares a wall with ..."

Reviewed on Sep 18, 2026

Moss Vale Holiday Park

43/53 Willow Drive Moss Vale NSW

$89 nightly

$89 total

Oct 19 - Oct 20

Total with taxes and fees

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.