Southern Highlands Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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 favourite 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.
Top Southern Highlands Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Kith Hotel Darling Harbour
Pyrmont
Price was CA $3,799, price is now CA $3,117 per person
CA $3,117
per person
Oct 13 - Oct 18
found 5 hours ago
Roundtrip flight included
Montreal (YUL) to Sydney (SYD)
8.8/10 Excellent! (499 reviews)
Excellent location, perfect for a stay in Sydney with car park location immediately adjacent to hotel
Reviewed on Aug 2, 2026
Rydges Darling Square Apartment Hotel
Sydney Central Business District
Price was CA $3,777, price is now CA $3,315 per person
CA $3,315
per person
Oct 13 - Oct 18
found 5 hours ago
Roundtrip flight included
Montreal (YUL) to Sydney (SYD)
8.8/10 Excellent! (1,563 reviews)
A great central to everything location. A short walk to train station and over to Darling Harbour. We went to the theatre and yet again just a short walk.
The property was well presented. The breakfast well worth it. Really enjoyed our stay.
The only downside was the communication with our booking we requested two beds in one of our two rooms booked. They had missed my emails and only prepared a queen size and had to quickly organise a trundle bed shoved in the room. This wasn’t ideal but we just dealt with it. This wouldn’t stop me from staying there again though as the in house customer service was good.
Reviewed on Jul 22, 2026
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
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.
Southern Highlands Hotel Deals
Berrima Bakehouse Motel
19 Old Hume Highway Berrima NSW
The price is CA $148 per night from Aug 10 to Aug 11
CA $148
CA $165 total
Aug 10 - Aug 11
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
"The hotel is lovely and staff friendly Wonderful location"
Reviewed on Jul 31, 2026
The Gibraltar
Boronia Street (off Centennial Road) Bowral NSW
Fully refundableReserve now, pay when you stay
The price is CA $237 per night from Aug 5 to Aug 6
CA $237
CA $261 total
Aug 5 - Aug 6
includes taxes & fees
8.4/10 Very good! (1,001 reviews)
"Nice property, rooms where modern and nice."
Reviewed on Aug 1, 2026
The Dormie House - On The Golf Course
Arthur Street Moss Vale NSW
Fully refundableReserve now, pay when you stay
The price is CA $125 per night from Aug 9 to Aug 10
CA $125
CA $138 total
Aug 9 - Aug 10
includes taxes & fees
8/10 Very good! (680 reviews)
"Quant place to stay. Smal room but cosy and pre-heated."
Reviewed on Jul 19, 2026
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.
Stay near popular Southern Highlands attractions
What to do in Southern Highlands
Personalised wine tour experience in the beautiful NSW Southern Highlands
CA $241
per adult
Sydney Wine Tasting & Southern Highlands with Pick up & drop off
CA $445
per adult
Frequently asked questions
Explore a world of travel with Expedia
- Misty farm possum cottage surrounding farmland
- Cottages in Berry
- Crystal Creek Meadows Luxury Cottages
- Coledale Hotels
- Vitamin Sea
- Broughton Cottage
- Figtree Hotels
- The Berry Inn
- Camden Park Hotels
- Saddleback Mountain Hotels
- The Hollows
- Warrawong Hotels
- Cabin Rentals in Berry
- Yellow Rock Hotels
- Archies
- Nowra Hotels
- Berry Hotels
- Woodhill Hotels
- Penrose Hotels
- Saddleback Cottage
- Our Beach House at Husky
- Apartments in Illawarra
- Farmborough Heights Hotels
- Luxury Hotels in Illawarra
- Riverbank Cottage & Studio
- North Wollongong Hotels
- Hotels with smoking rooms in South Coast
- Windmill Motel
- Beach Hotel Hotels in Berry
- Berkeley Hotels
- Lgbt Friendly Hotels in Shoalhaven City Council
- Kiama Heights Hotels
- Tasman Holiday Parks
- Cabin Rentals in South Coast
- Pass and Pause Bedsit Holiday Accommodation
- The Belmore Apartments Hotel
- Picton Hotels
- Huskisson Beach Resort
- Kiama Hotels
- Oceanfront Hotels in Illawarra
- 4 Star Hotels in Berry
- Casa Blu – steps from Culburra Beach's blue waters
- Alh Group Hotels in Illawarra
- Fairy Meadow Hotels
- Huskisson Hotel
- Wollongong Hotels
- Apartments in Penrose
- Hotels near Sea Cliff Bridge
- Romantic Hotels in High Range
- 4 Star Hotels in South Coast
- Moss Vale Hotels
- Flights from Robertson
- Flights to Kiama
- Flights from Medway
- Flights from Cataract
- Flights from Southern Highlands
- Flights from Picton
- Flights from Bundanoon
- Flights to Macarthur
- Flights from Cessnock (CES) to Shellharbour (WOL)
- Flights from Raleigh (RDU) to Shellharbour (WOL)
- Flights from Winnipeg (YWG) to Shellharbour (WOL)
- Flights to Wollongong
- Flights from Bangkok (BKK) to Shellharbour (WOL)
- Flights to Berry
- Flights from Avon
- Flights from Wollongong
- Flights from Dammam (DMM) to Shellharbour (WOL)
- Flights from Big Hill
- Flights from Orient Point
- Flights from Bamarang
- Collingwood Beach
- Pet-Friendly Vacation Packages South Coast
- Visit Kangaroo Valley
- Assembly Hall of Jehovah's Witnesses
- Berry Vacations
- Visit Illawarra
- Visit Gerringong
- Visit South Coast
- Appin Vacations
- Visit Wollongong
- Visit Hyams Beach
- Visit Bowral
- Wollongong Vacations
- Visit Burradoo
- Visit Stanwell Tops
- Wollongong City Beach
- Visit Berry
- Visit Coledale
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
