Southern Highlands Luxury Holidays

Book a Luxury Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to £335 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Packages with flights are ATOL protected

All you need to know about luxury holidays in Southern Highlands

What can I expect from a luxury Southern Highlands holiday?

Luxury on holiday is all about relaxing and feeling good. Whether you choose a sumptuous spa, Michelin-starred restaurant or super-king bed is your call. Use our amenities filters to find the things that tick all your boxes.

How can I find all-inclusive luxury holidays in Southern Highlands?

Tick the all-inclusive and 5-star filters to find the crème de la crème of Southern Highlands holidays. With everything included in the package price, you can drink and dine to your heart’s content, without worrying about that bill at the end.

Can I book a cheap luxury holiday to Southern Highlands?

A luxury holiday doesn’t have to break the bank. Travel out of peak season, choose a hotel or resort a little way out or go for a last-minute getaway and you’ll find some cracking deals. Sort by price to find luxury holidays to Southern Highlands starting at . Prices and availability are subject to change. Additional terms may apply.

Are there luxury spa holidays in Southern Highlands?

For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal Southern Highlands spa hotel. Book a whole weekend soaking away your stresses, or hop into the spa after the beach, some golf or a local advent-ahhhh.

What should I look for when booking a luxury family holiday in Southern Highlands?

Luxury isn’t just for adults. Those little touches designed for little people make a family holiday genuinely stress free … which is the greatest luxury of all. Look for spacious suites, pools toddlers can splash in, and breakfast buffets with waffles, pancakes and Nutella galore.

Can I book luxury last-minute holidays to Southern Highlands?

You can wangle a top-notch luxury holiday in Southern Highlands for a fraction of the normal price by booking last minute. Just enter your dates and see what’s available – if you’re flexible ... even better!

Can I book a luxury holiday in Southern Highlands with free cancellation and/or flexible dates?

If you’re splashing out on a luxury holiday, make sure your money is safe by booking with free cancellation. Just use the fully refundable filter and make sure you read all the terms and conditions.

Why should I book my luxury travel to Southern Highlands with Expedia?

Nobody does luxury quite like Expedia. With so many gorgeous properties in Southern Highlands to choose from, as well as access to first-class flight deals and hire cars with horsepower, there’s no better place to book.

Top Luxury Southern Highlands Hotels

Milton Park Country House Hotel & Spa

Milton Park Country House Hotel & Spa

5 out of 5
200 Horderns Road, Bowral, NSW
  • 20 min drive from Bendooley Estate Book Barn
Stay at this 5-star luxury hotel in Bowral. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff in their reviews. Popular ...
8.8/10 Excellent! (480 reviews)
"A great staycation in the Southern Highlands. Lovely staff and beautiful grounds to walk around in."

Reviewed on 16 Jul 2025

Milton Park Country House Hotel & Spa
Park Proxi Gibraltar Bowral

Park Proxi Gibraltar Bowral

3.5 out of 5
Boronia Street (off Centennial Road), Bowral, NSW
  • 8 min drive from Bendooley Estate Book Barn
Stay at this 3.5-star 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 ...
8.4/10 Very Good! (1,000 reviews)
"I loved our stay at Park Proxi. It worked for our family even though we aren't golfers. The room was spacious. Our toddler could walk"

Reviewed on 13 Aug 2025

Park Proxi Gibraltar Bowral
Peppers Craigieburn

Peppers Craigieburn

4.5 out of 5
Centennial Road, Bowral, NSW
  • 7 min drive from Bendooley Estate Book Barn
Stay at this 4.5-star luxury hotel in Bowral. Enjoy free parking, a golf course and room service. Our guests praise the helpful staff in their reviews. Popular ...
8/10 Very Good! (998 reviews)
"Staff and common areas excellent. Rooms warm and clean but tight and bathroom needs ventilation."

Reviewed on 20 Jul 2025

Peppers Craigieburn
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.

More holidays you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.