Luxury Holidays Southern Highlands

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$2,500 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top flight + Luxury hotel deals in Southern Highlands

Price found within the past 48 hours. Click for updated prices.
Links House

Links House

Burradoo
AU$1,313
per person
30 Oct - 6 Nov
found 1 day ago
Return flight included
Brisbane (BNE) to Sydney (SYD)
9/10 Wonderful! (799 reviews)
This restaurant is not a part of the Golf Club! It is an old but nice "guesthouse" that has been modernised and extended out to provide a more roomy bedroom. The attached Ethos Restaurant was high quality and we enjoyed our dinner there. Breakfast in the same space was well provided and enjoyed.

Reviewed on 31 Aug 2026

Ardour Milton Park Bowral

Ardour Milton Park Bowral

Save 100% on your flight
AU$2,456
per person
30 Oct - 6 Nov
found 1 day ago
Return flight included
Brisbane (BNE) to Sydney (SYD)
8.6/10 Excellent! (4 reviews)
Peppers Craigieburn

Peppers Craigieburn

AU$1,434
per person
30 Oct - 6 Nov
found 1 day ago
Return flight included
Brisbane (BNE) to Sydney (SYD)
8/10 Very good! (1,000 reviews)
The Gibraltar

The Gibraltar

AU$1,434
per person
30 Oct - 6 Nov
found 1 day ago
Return flight included
Brisbane (BNE) to Sydney (SYD)
8.6/10 Excellent! (1,008 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Southern Highlands
View all trips

5* Luxury holidays in Southern Highlands

Price found within the past 48 hours. Click for updated prices.
Ardour Milton Park Bowral

Ardour Milton Park Bowral

Save 100% on your flight
AU$2,456
per person
30 Oct - 6 Nov
found 1 day ago
Return flight included
Brisbane (BNE) to Sydney (SYD)
8.6/10 Excellent! (4 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Southern Highlands
View all trips

How to find luxurious holiday packages in Southern Highlands?

How to find a luxury holiday in Southern Highlands?

Whether you fancy heading off on an unforgettable spa break or relaxing on an all-inclusive vacation, finding your perfect 2026 luxury escape Southern Highlands couldn’t be easier. Use Expedia’s filters to find luxury escapes Southern Highlands hotels and luxury holiday rentals with the amenities you need to make your holiday extra special.

How to book a luxury holiday in Southern Highlands with Expedia?

Once you’ve identified your ideal luxury holiday Southern Highlands you simply need to enter your travel dates to view your travel and accommodation options. You can select from luxury holiday rentals to luxury hotels. Use the filters to find luxury escapes Southern Highlands deals around your selected dates and you could save money too.

Are luxury holidays in Southern Highlands worth the cost?

Memories are priceless so splashing out on luxury getaways to Southern Highlands in 2026 can be well worth the extra expense. That said, there are some great value luxury escapes Southern Highlands deals available if you’re prepared to book a holiday out of season. Consider booking villas or luxury holiday homes in Southern Highlands for a group or larger family holiday to keep costs down.

How do I choose the perfect luxury holiday package for Southern Highlands?

Make sure you think carefully about what you want from your luxury holiday in Southern Highlands before you book. If you’re taking the kids, click on the “family-friendly” filter to find hotels with facilities they’ll love—along with a pool bar and sauna for the adults to enjoy.

Where can I find excellent deals on luxury holidays in Southern Highlands?

Luxury doesn’t have to cost the earth. If you’re looking for discount luxury escapes Southern Highlands deals, then Expedia can help. Whether you’re after cost-effective luxury weekend getaways to Southern Highlands or a longer trip with luxury hire car, use the filters to access some of the best deals available.

How to find luxury spa Southern Highlands holiday packages?

Expedia can help you discover some of the most luxurious spa hotels to fit your budget, taste, and dates. You can compare prices and read reviews before deciding. It’s also often possible to get a luxury holiday Southern Highlands with free cancellation too, so you can book with confidence.

How to discover last-minute luxury holiday deals to Southern Highlands with Expedia.

While booking ahead is a good way to seal in some great value deals, it’s also possible to access top-notch last-minute luxury escapes to Southern Highlands. Simply enter your dates to see what’s on offer, and if you can be flexible about flights and hotels, so much the better for your pocket.

How to find luxury pet-friendly Southern Highlands holiday packages?

If you don’t want to leave your pet at home, no problem. It doesn’t mean you have to miss out on luxury facilities. Use the “pet-friendly” filter to find luxury escapes Southern Highlands hotels that will welcome your furry friend.

How to find great luxury beach holiday packages in Southern Highlands?

To discover some of the most luxurious beach lodgings available, tick the “all-inclusive” and “sea view” filters. You’ll be able to select from a big selection of luxury escape Southern Highlands hotels and apartments with direct access to beaches.

Why book luxury holiday packages in Southern Highlands with Expedia?

Expedia’s handy travel filters can help you search through a huge number of options and book a luxury escape Southern Highlands you’ll never forget. From rooms with a view to resorts with top-rated golf courses, you can customise your vacation and find one that ticks all your boxes.

Top Luxury Southern Highlands Hotels

Ardour Milton Park Bowral

Ardour Milton Park Bowral

200 Horderns Road Bowral NSW
  • 20 min drive from Bendooley Estate Book Barn
Stay at this luxury hotel in Bowral. Enjoy free Wi-Fi, free parking and a full-service spa. Our guests praise the helpful staff in their reviews. Popular attractions ...
Ardour Milton Park Bowral
The Gibraltar

The Gibraltar

Boronia Street (off Centennial Road) Bowral NSW
  • 8 min drive from Bendooley Estate Book Barn
Stay at this golf hotel in Bowral. Enjoy free Wi-Fi, free parking and a golf course. Our guests praise the helpful staff and the spacious rooms in their reviews. ...
The Gibraltar
Peppers Craigieburn

Peppers Craigieburn

Centennial Road Bowral NSW
  • 7 min drive from Bendooley Estate Book Barn
Stay at this luxury hotel in Bowral. Enjoy free parking, a golf course and room service. Our guests praise the helpful staff in their reviews. Popular attractions ...
Peppers Craigieburn
See all 1,638 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.

Activities

Highland Vines

Personalised wine tour experience in the beautiful NSW Southern Highlands

AU$245
per adult
Personalised wine tour experience in the beautiful NSW Southern Highlands
Sydney Wine Tasting & Southern Highlands with Pick up & drop off

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

AU$455
per adult
Sydney Wine Tasting & Southern Highlands with Pick up & drop off
See all activities in Southern Highlands
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.