Book Holiday Homes in Southern Highlands

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Featured Holiday Homes in Southern Highlands

Daphne cottage - Heritage two storey 2 bedroom cottage in Historical Berrima

Daphne cottage - Heritage two storey 2 bedroom cottage in Historical Berrima

Berrima
With a stay at this vacation home in Bowral (Berrima), you'll be within a 10-minute walk of Berrima Gaol and Berrima Courthouse.
Daphne cottage - Heritage two storey 2 bedroom cottage in Historical Berrima
Stately Bowral Designer Home

Stately Bowral Designer Home

East Bowral
The price is AU$736 per night from 23 May to 24 May
AU$736
per night
23 May - 24 May
Located in Bowral, this vacation home is in a rural location, a 5-minute drive from International Cricket Hall of Fame and 5 minutes from Bowral Golf ...
Stately Bowral Designer Home
Casa Antica, 200m walk to Bowral Township, family friendly

Casa Antica, 200m walk to Bowral Township, family friendly

Bowral
A stay at this vacation home places you in the heart of Bowral, within a 10-minute walk of Corbett Gardens and International Cricket Hall of Fame.
Casa Antica, 200m walk to Bowral Township, family friendly
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Sasarfras, Robertson

Sasarfras, Robertson

Robertson
Located in Robertson, this vacation home is in a rural location, a 2-minute drive from Robertson Nature Reserve and 6 minutes from Macquarie Pass National ...
Sasarfras, Robertson
Kerriedancer House, Southern Highlands

Kerriedancer House, Southern Highlands

Sutton Forest
Located in Sutton Forest, this vacation home is in a rural location, within a 10-minute drive of Southern Highland Wines and St. Maur Wines.
Kerriedancer House, Southern Highlands
Timbalah - a luxurious country retreat

Timbalah - a luxurious country retreat

Fitzroy Falls
When you stay at this vacation home in Fitzroy Falls, you'll be next to a golf course, within a 5-minute drive of Fitzroy Falls & Visitor Centre and Morton National ...
Timbalah - a luxurious country retreat
Luxury Heritage Cottage In The Heart Of Town

Luxury Heritage Cottage In The Heart Of Town

Mittagong
A stay at this vacation home places you in the heart of Mittagong, within a 5-minute drive of Destination Southern Highlands and Mount Gibraltar Reserve.
Luxury Heritage Cottage In The Heart Of Town
Heart of the Southern Highlands, 14 to 16 guests. Specialising in large groups.

Heart of the Southern Highlands, 14 to 16 guests. Specialising in large groups.

Bowral
The price is AU$872 per night from 23 May to 24 May
AU$872
per night
23 May - 24 May
With a stay at this vacation home in Bowral, you'll be within a 5-minute drive of International Cricket Hall of Fame and Bowral Golf Course.
Heart of the Southern Highlands, 14 to 16 guests. Specialising in large groups.
Home among the Gum Trees

Home among the Gum Trees

Moss Vale
With a stay at this vacation home in Bowral (Moss Vale), you'll be a 4-minute drive from Morton National Park and 7 minutes from Moss Vale Golf Club.
Home among the Gum Trees
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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.

Southern Highlands Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Southern Highlands vacation homes are the perfect way for you to wing it.

Holiday houses in Southern Highlands let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Southern Highlands in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Southern Highlands adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Southern Highlands with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Southern Highlands vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Southern Highlands Holiday Homes essential information

Accommodation
202 Holiday Homes
Lowest Price
AU$155
Highest Price
AU$872
Popular accommodation
Daphne cottage - Heritage two storey 2 bedroom cottage in Historical Berrima, Stately Bowral Designer Home, Casa Antica, 200m walk to Bowral Township, family friendly, Sasarfras, Robertson, Kerriedancer House, Southern Highlands, Timbalah - a luxurious country retreat, Luxury Heritage Cottage In The Heart Of Town, Heart of the Southern Highlands, 14 to 16 guests. Specialising in large groups. , Home among the Gum Trees

Top trending hotels in Southern Highlands

Park Proxi Gibraltar Bowral

Park Proxi Gibraltar Bowral

3.5 out of 5
Boronia Street (off Centennial Road), Bowral, NSW
Fully refundableReserve now, pay when you stay
The price is AU$229 per night from 26 May to 27 May
AU$229
per night
26 May - 27 May
Located in Bowral, Park Proxi Gibraltar Bowral is in the mountains, within a 5-minute drive of Corbett Gardens and Centennial Vineyards.
Park Proxi Gibraltar Bowral
Berrima Bakehouse Motel

Berrima Bakehouse Motel

3.5 out of 5
19 Old Hume Highway, (entrance via Wingecarribee St), Berrima, NSW
The price is AU$155 per night from 23 May to 24 May
AU$155
per night
23 May - 24 May
With a stay at Berrima Bakehouse Motel in Bowral (Berrima), you'll be steps from Berrima Gaol and 3 minutes by foot from Berrima Courthouse.
Berrima Bakehouse Motel
Berida Hotel

Berida Hotel

4 out of 5
6 David Street, Bowral, NSW
The price is AU$223 per night from 23 May to 24 May
AU$223
per night
23 May - 24 May
A stay at Berida Hotel places you in the heart of Bowral, steps from Bowral Golf Course and a 2-minute drive from Corbett Gardens.
Berida Hotel
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The Imperial Motel

The Imperial Motel

4 out of 5
Cnr Bong Bong & Bundaroo Sts, Bowral, NSW
Fully refundableReserve now, pay when you stay
The price is AU$162 per night from 26 May to 27 May
AU$162
per night
26 May - 27 May
With a stay at The Imperial Motel in Bowral, you'll be within a 5-minute walk of Tractorless Vineyard and Corbett Gardens.
The Imperial Motel
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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.

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^Subject to availability and chosen travel dates.