Southern Highlands Vacation Packages 2026 from $1,345

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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.

Seaside Retreat With Parking and Balcony

Newport

$1,345

per person

Oct 22 - Oct 25

found 1 day ago

Roundtrip flight included

Los Angeles (QLA) to Sydney (SYD)

No reviews

North-east Facing Modern 2-bed Apartment

Freshwater

$1,707

per person

Oct 9 - Oct 12

found 12 hours ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Sydney (SYD)

No reviews

Elysium Manly

Manly

$2,194

per person

Nov 3 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Sydney (SYD)

9/10 Wonderful! (375 reviews)

This property was lovely and directly across from the beach. The staff were excellent, meals were fantastic and it was centrally located and walkable to shopping and enjoying the seaside board walk.

Reviewed on Aug 30, 2026

Medusa Boutique Hotel

Darlinghurst

$1,704

per person

Nov 3 - Nov 8

found 13 hours ago

Roundtrip non-stop flight included

New York (JFK) to Sydney (SYD)

9.6/10 Exceptional! (489 reviews)

Staff was very friendly and helpful and the hotel was a hidden treasure! Very well decorated, clean, with all the amenities you may need and the location was great! My room included a bottle of wine but front desk forgot to send it, but I still give them ⭐️⭐️⭐️⭐️⭐️ very recommended!

Reviewed on Aug 30, 2026

Luxury 2-bed With Ocean Views and Garden

Collaroy

$1,547

per person

Oct 22 - Oct 25

found 1 day ago

Roundtrip flight included

Los Angeles (QLA) 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.

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.

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.

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 top-notch restaurants.

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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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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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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 top-notch restaurants.

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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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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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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 top-notch restaurants.

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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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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

$109 nightly

$120 total

Sep 3 - Sep 4

Total with taxes and fees

9.4/10 Exceptional! (1,008 reviews)

"Great food"

Reviewed on Aug 31, 2026

The Gibraltar

Boronia Street (off Centennial Road) Bowral NSW

Fully refundableReserve now, pay when you stay

$170 nightly

$187 total

Sep 17 - Sep 18

Total with taxes and fees

Moss Vale Holiday Park

43/53 Willow Drive Moss Vale NSW

$99 nightly

$99 total

Sep 15 - Sep 16

Total with taxes and fees

8.8/10 Excellent! (69 reviews)

"The cabin was clean and had everything we needed. However the bedroom had only a narrow gap around the bed, which, as I have some difficulty moving around in tight spaces, was a bit of a problem. Similarly the bathroom was extremely small and anyone large or with difficulties walking would find it ..."

Reviewed on Aug 29, 2026

See all 1,640 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.