The Southern Highlands

We are expanding! If you are interested in listing your property with The Holidays Collection, please call us on 02 4411 7000.

With offices in Hyams Beach, Gerringong and Bowral, we are able to provide you with convenient customer service. Our great local knowledge of the locations of the holiday homes in our growing portfolio means we can always point you in the right direction, whatever your holiday requirements.

Location and Access 

The Southern Highlands encompasses many heritage towns and villages including Berrima, Bowral, Bundanoon, Fitzroy Falls, Mittagong, Moss Vale, Robertson, Sutton Forest, and Exeter, to name a few! The region is easily accessible, being a one and a half hour drive southwest of Sydney and just under two hours from Canberra. Regular trains are also available.  

Key Features and Attractions

Renowned for its many country charms, the Southern Highlands is home to many breathtaking walks, waterfalls, caves, cycling tracks, cellar doors, acclaimed restaurants, open gardens and so much more. Bowral is the main service town, and there are many annual events including Tulip Time in September, the Food and Wine Fesitval in October, and the Bong Bong Races in November. Many towns also host annual shows earlier in the year and of course, winter is always a wonderful time to visit this cold climate wine region. 

Click here to see our Southern Highlands properties... with more to come!

Items 1 to 12 of 12 on pages: 1
Large retreat for 16 with rural views, pool and 5 acres of grounds!
16Sleeps5Beds2Bathrooms4Cars
Highland House for 16, Southern Highlands

This stunning Highland home is a beautiful combination of stone, glass and timber. It is one of the few Southern Highlands' homes with a pool. With an oversized entertaining room, twoslow combustion wood fires, a gas fire and reverse-cycle air conditioning, it is a perfect retreat for a large group or a family gathering in all seasons. The decks have rural views over attractive gardens, a dam and the swimming pool.

From $1,360.00* daily
Holiday House in Colo Vale
Stunning, historic 1870's homestead with beautiful gardens!
14Sleeps7Beds4Bathrooms6Cars
Aylmerton House + Cottage for 14, Southern Highlands - 4pm Check Out Sundays

Aylmerton House is an iconic Southern Highlands home - one of the best in the district - that sleeps 14 in sumptuous comfort and luxury. This beautiful sandstone home was built in the 1870's and has 5 acres of lawns and gardens. The main house plus connected cottage has 7 bedrooms, 4 bathrooms, multiple living rooms, two fireplaces and lovely wrap around verandahs- making it a perfect gathering point for friends or families. Aylmerton House is the quintessential Southern Highlands experience!

From $700.00* daily
Holiday House in Mittagong
Stunning, historic 1870's homestead with beautiful gardens!
10Sleeps5Beds3Bathrooms6Cars
Aylmerton House for 10, Southern Highlands - 4pm Check Out Sundays

Aylmerton House is an iconic Southern Highlands home - one of the best in the district - that sleeps 10 in sumptuous comfort and luxury. This beautiful sandstone home was built in the 1870's and has 5 acres of lawns and gardens. The main house that you will use has 5 bedrooms, 3 bathrooms, multiple living rooms, two fireplaces and lovely wrap around verandahs- making it a perfect gathering point for friends or families. Aylmerton House is the quintessential Southern Highlands experience! If you wish to book the Cottage as well, look for our sleeps 14 configuration!

From $700.00* daily
Holiday House in Mittagong
Spacious retreat for 11 -  a rural farm stay in an idyllic bush setting.
11Sleeps5Beds3Bathrooms4Cars
Netley Lodge for 11, Southern Highlands - 4pm check out Sundays

This elevated rural property enjoys beautiful views of olive groves and 25 acres of rural and bush land with several dams. Guests will enjoy peace and tranquility in an idyllic natural environment. An ideal large home for a get together, the property has space for everyone and is perfect for both indoor and outdoor entertainment. Kids will love making and eating pizza from the built in brick pizza oven!

From $660.00* daily
Holiday House in High Range
The perfect weekend getaway in the Southern Highlands
10Sleeps6Beds2Bathrooms2Cars
Braeside, Southern Highlands - Stay 3, Pay 2 Friday Arrivals!

Braeside is a beautiful Federation Cottage in the heart of Bundanoon that has been cleverly extended to comfortably sleep 10 guests in 6 bedrooms. This stunning home is perfect for a group of friends attending a wedding, or as a perfect base to explore the Southern Highlands. Walk to town, explore Morton National Park, or take an easy drive to nearby wineries! All Friday arrivals offer a 3 nights for the price of 2 special. Just ask when you book!

From $600.00* daily
Holiday House in Bundanoon
Luxurious home for 8 surrounded by stunning 3 acre gardens
8Sleeps4Beds2Bathrooms4Cars
Mirrabooka, Burrawang - beautiful home and 3 acres of gardens in the Southern Highlands

Mirrabooka is a classic Southern Highlands experience - a beautifully decorated home, fireplace, chef's kitchen, verandahs, and 3 acres of lawns and mature cool climate gardens. This sumptuous home sleeps 8 across 3 bedrooms and a sofa bed room. It is pet friendly and only a short drive from Burrawang Village and its famous pub, butcher shop and cafes.

From $500.00* daily
Holiday House in Burrawang
Beautifully restored and full of character.
9Sleeps4Beds4Bathrooms3Cars
Mirriyindi - Unique Berrima escape for 9 in the Southern Highlands - 4pm check out Sundays

Down the driveway, under the weeping willow, through the poplar trees and the cherry blossoms, an idyllic and beautifully restored property is awaiting you. Set in just under two acres of lovely country gardens, the house and two cottages are all positioned with privacy in mind, yet there is also plenty of space to come together, making Mirriyindi perfect for groups of up to nine and a great option for your Southern Highlands stay.

From $500.00* daily
Holiday House in Berrima
Beautifully restored and full of character.
7Sleeps3Beds3Bathrooms3Cars
Mirriyindi - Unique Berrima escape for 7 in the Southern Highlands - 4pm check out Sundays

Down the driveway, under the weeping willow, through the poplar trees and the cherry blossoms, an idyllic and beautifully restored property is awaiting you. Set in just under two acres of lovely country gardens, the house and separate cottage are positioned with privacy in mind, yet there is also plenty of space to come together, making Mirriyindi perfect for groups of up to seven and a great option for your Southern Highlands stay.

From $450.00* daily
Holiday House in Berrima
Stylish, comfortable, perfectly located cottage for 9
9Sleeps4Beds1Bathrooms3Cars
Lou Lou's Cottage, Southern Highlands - 4pm Check Out Sundays

Lou Lou's Cottage is a stylish, comfortable, perfectly located home - sleeping up to 9 guests across 4 bedrooms. The Scottish Arms Hotel is just around the corner - walking distance - and Bowral town is a 3 minute drive! You will feel totally at home at this property which is immaculately presented and very well equipped and furnished!

From $400.00* daily
Holiday House in Bowral
A rural idyll in the heart of the Southern Highlands.
6Sleeps3Beds1Bathrooms3Cars
The Tor, Southern Highlands - 4pm Check Out Sundays

The Tor is an older style, classic Southern Highlands cottage. It is set on 25 peaceful acres, surrounded by seasonal gardens with many secret pockets! The house has been decorated in a period style, and is full of character, comfort and style - true to the photos. Beautiful Burrawang Village, Belmore Falls and Fitzroy Falls are all easy drives from The Tor - making it a great base from which to explore this beautiful district of NSW!

From $400.00* daily
Holiday House in Burrawang
Beautifully restored and full of character.
4Sleeps2Beds2Bathrooms3Cars
Mirriyindi - unique Berrima escape for 4 in the Southern Highlands - 4pm check out Sundays

Down the driveway, under the weeping willow, through the poplar trees and the cherry blossoms, an idyllic and beautifully restored property is awaiting you. Set in just under two acres of lovely country gardens, Mirriyindi is the perfect small family or couples getaway.

From $300.00* daily
Holiday House in Berrima
Available for both short term and long term stays.
4Sleeps2Beds1Bathrooms2Cars
Redwood Cottage - Burradoo getaway, Southern Highlands - 4pm Check Out Sunday

Full of character and charm, Redwood Cottage is a great option for your Southern Highlands getaway. It is an affordable, comfortable, rustic cottage that still has many of its original features including the kitchen and bathroom. The house is pet friendly with a fully fenced front and back yard. Redwood Cottage is available for holiday or permanent rentals.

From $200.00* daily
Holiday Cottage in Burradoo
Items 1 to 12 of 12 on pages: 1
* Indicative price only. Please select dates for more accurate rates. Conditions and additional charges may apply.