25 Best Vacation Rentals in Southern Highlands - Holiday Lettings - Cabins

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Apartments Bowral
12 properties
Berrima
5 properties

Southern Highlands

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27 Vacation rentals

4

Home rental in Bowral

Southern Highlands / Bowral

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Hart Haus is located in the heart of Bowral in the beautiful Southern Highlands. The property has all the inclusions of a 5 star hotel and is only a short walking distance to town, restaurants and many local attractions. The property is fully air-conditioned and boasts  …see more

from $262 / night

$1498 / week

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from $262 / night

19

Vacation home in Robertson

Southern Highlands / Robertson

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Madison Park is an elegant 5 bedroom, 5 bathroom home set on 30 acres at the edge of Robertson, surrounded by Babe country with stunning views of distant escarpments and rolling green hills. It is only a 3 minute drive to cafes and coffees in Robertson but the property  …see more

from $562 / night

$3930 / week

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from $562 / night

(3) Excellent 

11

Home rental in Bowral with golf nearby

Southern Highlands / Bowral

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Built originally in 1926 the beautifully presented Garden Keepers Cottage is just a stone's throw from Bowral shops and restaurants a minute to Harris Farm, a continental butcher a fantastic Italian restaurant - Café Rosso and a Chambers Liquor outlet, not to  …see more

from $224 / night

$1123 - $1700 / week

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from $224 / night

(2) Excellent 

7

Vacation barn in Berrima

Southern Highlands / Berrima

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Ask about children
  • Air conditioning
Guests of The Loch can reserve the whole house for groups of up to 8 people, or book an individual room. Our beautifully appointed suites offer luxurious comfort with bespoke detail and captivating views. Single or Twin bed options available by request. All rooms are eq  …see more

from $629 / night

$3743 / week

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from $629 / night

7

Southern Highlands / Bowral

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly

 …see more

from $79 / night

$337 - $468 / week

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from $79 / night

(2) Excellent 

32

Bowral Vacation home rental

Southern Highlands / Bowral

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Designer home with high ceilings. Outdoor spa. Polished wooden floors. Tranquil and quiet, super clean and modern - while also retaining some rustic charm. An Oasis from a busy life. Come relax and enjoy! Our lane is the most prestigious in East Bowral, located on a rid  …see more

from $375 / night

$2096 / week

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from $375 / night

6

Bowral Vacation b&b rental

Southern Highlands / Bowral

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Air conditioning
  • Private garden
HighlandBray is a self contained country studio that accommodates two guests located in tranquil and serene surrounds. Situated on small acreage, it has a rural outlook, beautiful lush gardens, plenty of bird life. HighlandBray is truly country, located at the Souther  …see more

from $90 / night

$524 / week

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from $90 / night

(3) Excellent 

33

Cottage rental in Berrima

Southern Highlands / Berrima

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
This is a beautiful 1843 historic cottage in the centre of Berrima Village. A great place to tour the Southern highland wineries, play golf, gather with friends for a relaxing getaway. It has recently been sympathetically restored to showcase its vibrant history. It has  …see more

from $203 / night

$1415 / week

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from $203 / night

(2) Excellent 

31

Home rental in Canyonleigh

Southern Highlands / Canyonleigh

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Secluded, modern, Australian luxury home in the Southern Highlands (Canyonleigh) near Berrima and Bowral, just under 2 hours from Sydney. 3 bdr, spacious living, chef's kitchen, 100+ acres of bush, uninterrupted views, fully equipped. Perfect for a romantic sojourn  …see more

from $330 / night

$1498 / week

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from $330 / night

15

Vacation home in Berrima

Southern Highlands / Berrima

9 26 Min stay varies

  • 9 bedrooms
  • Sleeps 26
  • Min stay varies
  • Child friendly
  • Private garden
Sleeping 26 comfortably without the need for bunks, roll aways or sofa beds, Berrima Retreat provides premier self-contained accommodation for large groups. Berrima Retreat makes a great base for attending weddings at major nearby venues, or for wine tasting at all the  …see more

from $1032 / night

$7221 / week

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from $1032 / night

(1) Excellent 

39

Vacation home in Bowral

Southern Highlands / Bowral

4 13 2 nights min

  • 4 bedrooms
  • Sleeps 13
  • 2 nights min
  • Child friendly
  • Pet friendly
Located on just under an acre of lovely lawns and gardens in Burradoo, Birchgrove Cottages offers 2 beautiful separate cottages, sleeping large groups in comfort. Located in the lovely Southern Highlands, it is only minutes walk into Bowral town centre and seconds to th  …see more

from $375 / night

$2620 / week

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from $375 / night

(1) Excellent 

8

Guest house accommodation in Bowral with indoor pool, golf nearby

Southern Highlands / Bowral

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Stay a night or a week you wont find a better place to unwind. Kirkham Manor invites you to relax and do 'nothing, or do 'everything' !Offering accommodation for 2-10 people in a park-like setting. Guests have the use of a fully self-contained 3  …see more

from $64 / night

$846 / week

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from $64 / night

(1) Excellent 

7

Southern Highlands / Burrawang

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Private garden

 …see more

from $150 / night

$1048 / week

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from $150 / night

(1)  

46

Home rental in Bundanoon

Southern Highlands / Bundanoon

7 16 2 nights min

  • 7 bedrooms
  • Sleeps 16
  • 2 nights min
  • Child friendly
  • Private garden
La Belle Vie consists of a large house and separate cottage set on 5 park-like acres at the end of a winding country lane and offers complete privacy, yet is only a 20 minute stroll to the country village of Bundanoon. ​La Belle Vie oozes charm and character with lar  …see more

from $749 / night

$7935 - $10554 / week

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from $749 / night

(2) Excellent 

21

Bowral Vacation chalet rental

Southern Highlands / Bowral

13 36 2 nights min

  • 13 bedrooms
  • Sleeps 36
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
The Pill Factory was built circa 1870 by Augustus Nicholas and was originally named The Golden Cross Pill Factory. Extensively renovated in the 1930's into a guesthouse this 3 storey character sandstone building is perfect for families and groups to hold events or  …see more

from $749 / night

$6737 / week

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from $749 / night

13

Australia & New Zealand Vacation home rental

New South Wales / Southern Highlands

7 20 2 nights min

  • 7 bedrooms
  • Sleeps 20
  • 2 nights min
  • Child friendly
  • Ask about pets
Positioned along the Corang River Southern Highlands in NSW is the majestic Dungowan. The natural beauty of the two hundred and thirty three acre estate is remarkable. Theres a mixture of landscapes theres pine forests open grassed areas river banks perfect spaces to e  …see more

from $1310 / night

$9170 / week

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from $1310 / night

10

Vacation home in Berrima

Southern Highlands / Berrima

8 16 2 nights min

  • 8 bedrooms
  • Sleeps 16
  • 2 nights min
  • Child friendly
  • Pet friendly
Dixieland estate is a beautifully appointed holiday letting located at the heart of historic Berrima in the Southern Highlands of NSW. Set in a rolling landscape, our property exudes warmth and modern ambiance combined with the charm of country elegance. Dixieland Estat  …see more

from $1161 / night

$5441 - $6542 / week

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from $1161 / night

16

Vacation home with golf nearby in Bowral

Southern Highlands / Bowral

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
Woodcote is a large 2 storey french provincial style country home circa 1915 set on a 1/2 acre of gardens, offering complete privacy, and less than 5 minutes walk from Bowral town centre, Bradman & International Cricket Hall of Fame Museum, Bowral Golf course, Empire Ci  …see more

from $899 / night

$4791 - $9132 / week

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from $899 / night

18

Vacation home in Robertson

Southern Highlands / Robertson

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
Brenchley Farm is perfect for families, friends or couples looking for a special getaway. It's your country retreat in the heart of the Southern Highlands offering peace and tranquility, comfort and convenience. Enjoy the modern, well equipped, 4 bedroom, 2 bathroom ho  …see more

from $330 / night

$2620 - $3384 / week

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from $330 / night

13

Bowral Vacation home rental

Southern Highlands / Bowral

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Pet friendly
  • Private garden
Be greeted by a touch of Provence in the heart of the Highlands. An oasis of calm and charm. Saint Eloi Guesthouse comfortably sleeps up to 8 adults. Surrounded by leafy gardens, you will feel at ease in secluded surroundings, yet close enough to Bowral town centre to  …see more

from $386 / night

$2699 / week

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from $386 / night

(1) Excellent 

9

Vacation cottage in Fitzroy Falls

Southern Highlands / Fitzroy Falls

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly
Experience a romantic and unique s/c farm stay in a 1920's train carriage on Redleaf Farm. A small working farm adjacent to state forest, Redleaf Farm is an ideal getaway in the NSW Southern Highlands. The Carriage 1238 has a king bed 'compartment', a dressing room '  …see more

from $188 / night

$1310 / week

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from $188 / night

(5) Excellent 

16

Southern Highlands / Robertson

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Nearest beach 60 mi
  • Child friendly
  • Air conditioning

 …see more

from $169 / night

$1123 - $2171 / week

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from $169 / night

18

Southern Highlands / Bowral

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Air conditioning
  • Private garden

 …see more

from $120 / night

$839 / week

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from $120 / night

24

Southern Highlands / Berrima

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from $899 / night

$6288 - $7860 / week

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from $899 / night

22

Southern Highlands / Sutton Forest

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Ask about pets

 …see more

from $742 / night

$5188 - $9432 / week

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from $742 / night

18

Southern Highlands / Bowral

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from $674 / night

$4716 - $6737 / week

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from $674 / night

8

Southern Highlands / Sutton Forest

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly

 …see more

from $225 / night

$1423 / week

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from $225 / night

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