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 24 of 24 on pages: 1
47Sleeps20Beds10Bathrooms15Cars
LITTLE FOREST, Alpine, Southern Highlands - 4pm Check Out Sundays!

Located in Alpine in the beautiful Southern Highlands, Little Forrest is a secluded property ideal for hosting large groups. The property consists of 7 unique cottages set on 40 acres of lawn, gardens, waterways and bush. When you book the entire property you have exclusive access to all 7 cabins, giving you 20 bedrooms and 10 bathrooms, enough to accommodate up to 47 people. A number of the cottages are pet friendly and the extensive outdoor area make this an ideal location for outdoor activities. You can even meet the resident Shetland ponies and alpacas.

From $3,200.00* daily
Holiday Cottage in Alpine
Iconic luxury for 19 guests - set amidst 7 acres in the heart of Bowral!
19Sleeps9Beds5Bathrooms5Cars
EARLSBRAE, Bowral, Southern Highlands - 4pm Check Out Sundays

Earlsbrae is an iconic and luxurious Bowral home. Built in the 1870s, the property has been stylishly renovated, yet still maintains the beautiful period architecture that connects its guests to a rich history. Set on 7 acres of beautiful established gardens, Earlsbrae can accommodate up to 19 guests across 9 bedrooms. Once in house, it is a pleasant stroll or short drive to Bowrals shops, cafes and restaurants. Or if you prefer to stay in, there is plenty to keep you entertained and comfortable including a clay tennis court, billiards room, grand piano, easy access to Mt Gibraltars walking trails, smart TVs, a modern, fully equipped kitchen and 5 renovated bathrooms. Please also note that due to the high standards of this beautiful home, party groups are not accepted, smoking inside is not permitted, and a cash bond of $2,000 applies to every booking.

From $2,500.00* daily
Holiday House in Bowral
Stunning Highlands homestead with swimming pool and spa.
11Sleeps4Beds3Bathrooms5Cars
Wembley House, Southern Highlands - with 4pm Check Out Sunday!

Wembley is a one of a kind in the Southern Highlands - a historic, stylish and captivating home set amongst an oasis of landscaped gardens. The home has soaring 3 metre ceilings and incorporates reclaimed doors and stained glass windows from the Queen Victoria Building and Carrington Hotel! Wembley is set on 11 acres and has an incredible array of features:pool and spa, luxurious pool cabana with its own kitchen, bathroom and bedroom, adjoining indoor-outdoor entertaining area that combines the best of a shearing shed, sports bar and BBQ, a half basketball court, trampoline, herb garden, chicken run, farm animals, and plenty of parking for guests! Wembley is therefore a perfect retreat and is located just west of Berrima town - an easy drive to cafes, restaurants, wedding venues, wineries and the like.

From $1,450.00* daily
Holiday House in Berrima
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 $1,290.00* 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 $1,000.00* daily
Holiday House in Mittagong
An impressive architect-designed property with bushland vistas
10Sleeps5Beds4Bathrooms5Cars
ALPINE LODGE, Alpine, Southern Highlands - 4pm Check Out Sundays!

Just over an hours drive from Sydney, Alpine Lodge is the perfect luxury country getaway. Set on 22 acres, this architecturally designed home boasts beautiful bush views and luxurious modern amenities. With 5 bedrooms, 4 bathrooms, large fully equipped kitchen and generous living spaces, Alpine Lodge can accommodate up to 10 people. Fireplaces and heated floors will keep you warm in winter and air conditioning will keep you cool in summer. Mittagong and Bowral are both within a 10-15 drive from the property. All that the Southern Highlands has to offer is within easy driving distance.

From $975.00* daily
Holiday House in Alpine
14Sleeps4Beds3Bathrooms4Cars
LAVENDER COTTAGE, Alpine, Southern Highlands - 4pm Check Out Sundays!

Lavender Cottage is a beautiful home located on 40 acres of gardens and bush in Alpine, Southern Highlands. The timber floorboards and exposed roof beams give this property a wonderful country feel. You will not miss out on modern conveniences however, with a large modern kitchen, flat screen televisions and air conditioning upstairs. This home sleeps up to 14 people across 4 bedrooms, and has 3 bathrooms. Children are well catered for with large lawns and gardens to explore and even a tree house. Lavender House is a charming and spacious base for enjoying all that the Southern Highlands has to offer.

From $800.00* daily
Holiday Cottage in Alpine
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
Available for both short term and long term stays.
6Sleeps3Beds2Bathrooms2Cars
KIRRIEMUIR - Burradoo, Southern Highlands - 4pm Check Out Sunday

Kirriemuir is a luxurious and beautifully decorated retreat in Burradoo - ideal for 3 couples. Families may also stay of course, but due to the nature of this house, children under 8 are not permitted - sorry! The home is stylish, sumptuous and equipped with everything you could wish for - including complimentary home roasted coffee, wine and other treats upon arrival. Beds are super comfortable, the garden is large and you will be very centrally located - so a perfect base for exploring the Southern Highlands!

From $700.00* daily
Holiday House in Burradoo
9Sleeps7Beds2Bathrooms4Cars
THE ANGAS CARRIAGE, Alpine, Southern Highlands - 4pm Check Out on Sundays!

Staying in The Angas Carriage is a truly unique and enjoyable experience. Angas started life as a passenger train in the 1920s and has been loving restored and converted into accommodation for up to 9 guests. The original woodwork and compartment layout make this a beautiful place to be. Modern updates including insulation, kitchen, bathroom, heating and air conditioning ensure that Angas remains comfortable for guests all these years later. This is an accommodation experience that you will not forget.

From $600.00* daily
Holiday Cottage in Alpine
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 $580.00* daily
Holiday House in Berrima
Stylish home for 9 with games room a bonus!
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 games room with pool table and table tennis is also a bonus! The Scottish Arms Pub 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, well equipped and well furnished!

From $550.00* daily
Holiday House in Bowral
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 $550.00* daily
Holiday House in High Range
Spacious and stylish home that is walking distance from Burrawang main street
6Sleeps3Beds3Bathrooms3Cars
CHESTNUT TREES, Burrawang - 4pm check out Sundays

Chestnut Trees is a beautiful, architect designed home, set on 2 acres and within walking distance of Burrawang's cafe, pub and main street. The home has a separate master bedroom wing, cathedral ceilings, generous open plan living areas, plenty of natural light, and beautiful trees and gardens (including of course Chestnut Trees!). It is a perfect, stylish and quintessential Southern Highlands getaway for 6!

From $525.00* daily
Holiday House in Burrawang
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 $510.00* daily
Holiday House in Berrima
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
8Sleeps3Beds1Bathrooms2Cars
OATLEY COTTAGE, Alpine, Southern Highlands - 4pm Check Out on Sundays!

Oatley Cottage was originally built in 1910 in the Sydney suburb of Oatley. It was transported to Little Forrest in 2009 and lovingly restored. The cottage has a wonderful homely feel to it and is a wonderful retreat to come home to after a day exploring the Southern Highlands.

From $500.00* daily
Holiday Cottage in Alpine
5Sleeps2Beds2Bathrooms2Cars
THE POTTERY COTTAGE, Alpine, Southern Highlands - 4pm Check Out Sundays!

The Pottery Cottage started life as a pottery studio bu has been lovingly converted into a comfortable, characterful cottage. There are two bedrooms, each with ensuite and bedding for 5 guests. The design of the living area and bedrooms makes extensive use of beautiful timber cladding and a double height ceiling with exposed timber joists. During the colder months, the fireplace makes this a wonderful cozy place to be.

From $400.00* daily
Holiday Cottage in Alpine
4Sleeps2Beds1Bathrooms2Cars
STUDIO COTTAGE, Alpine, Southern Highlands - 4pm Check Out Sundays!

Studio Cottage is a truly unique property that offers guests a charming country getaway. The cottage was built by artist Ray Crooke as his studio in the 1970s. The sandstone he used was originally hand quarried by convicts and was reclaimed from the old Kerrigans Inn. The cottage has a wonderful cozy feel to it and is a wonderful retreat to come home to after a day exploring the Southern Highlands.

From $350.00* daily
Holiday Cottage in Alpine
4Sleeps1Beds1Bathrooms1Cars
ORCHARD COTTAGE, Alpine, Southern Highlands - 4pm Check Out on Sundays!

Orchard Cottage is a two storey cottage set in the orchard of Little Forrest. The cottage has a warm, rustic ambience and is comfortable for groups up to four people. Downstairs is a wonderful social area, consisting of the kitchen and living area. Combined with a wood heater, this is the perfect area to curl up with a book or to watch a movie. Upstairs is a large combined sleeping area with bathroom.

From $300.00* daily
Holiday Cottage in Alpine
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 $300.00* daily
Holiday House in Burrawang
A new purpose-built luxury Victorian style weatherboard cottage with an elegant, modern country feel
4Sleeps2Beds1Bathrooms1Cars
Rose Cottage, Bowral, Southern Highlands

Rose cottage is a Victorian-style weatherboard cottage with an elegant, modern country feel. Rose cottage is set on a beautiful 1-acre garden estate in Burradoo (Bowral) in the grounds of Bromley Lodge (where the owners reside). It is far enough apart and oriented in such a way as to offer privacy for owners and guests alike.

From $290.00* daily
Holiday Cottage in Burradoo
3Sleeps1Beds1Bathrooms1Cars
ECO COTTAGE, Alpine, Southern Highlands - 4pm Check Out on Sundays!

This pretty country cottage has been built to provide a comfortable stay with a low ecological impact. This has been achieved with a water tank, low energy hot water system and enviro cycle septic system. The cottage makes use of recycled timber, windows and materials. This gives the cottage wonderful personality without compromising comfort.

From $250.00* daily
Holiday Cottage in Alpine
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 24 of 24 on pages: 1
* Indicative price only. Please select dates for more accurate rates. Conditions and additional charges may apply.