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

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Apartments Bowral
10 properties

Southern Highlands

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24 Vacation rentals

(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 $376 / night

$2631 / week

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from $376 / 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 menti …see more

from $224 / night

$1128 - $1706 / week

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from $224 / night

(3) 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 $376 / night

$2105 / week

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from $376 / 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 $897 / night

$4782 - $9115 / week

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from $897 / night

13

Southern Highlands 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 $1308 / night

$9153 / week

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from $1308 / 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 $91 / night

$527 / week

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from $91 / 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 bedroom, 2 bath …see more

Pricing unknown

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Pricing unknown

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 $331 / night

$2631 - $3397 / week

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from $331 / night

(1) Excellent 

16

Vacation home rental

Southern Highlands / Robertson

5 16 2 nights min

  • 5 bedrooms
  • Sleeps 16
  • 2 nights min
  • Nearest beach 35 mi
  • Child friendly
  • Private garden
Sassafras House, Robertson is the perfect family retreat for the extended family or large group. With a fully equipt kitchen and large dining table it's ready for a large dinner party. With every bed made with your comfort in mind you will relax and unwind without hav …see more

from $264 / night

$1879 / week

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from $264 / 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, fam …see more

from $369 / night

$2578 / week

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from $369 / night

(4) 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 $632 / night

$3758 / week

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from $632 / night

(4) Excellent 

55

Cottage rental in Berrima

Southern Highlands / Berrima

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Nearest beach 70 mi
  • Child friendly
  • Private garden
This is a beautiful 1843 historic cottage in the centre of stunning Historic Berrima Village. A great place to tour the Southern Highland wineries, play golf, hike, cycle or simply gather with family and friends for a relaxing getaway. It has recently been sympathetical …see more

from $226 / night

$1579 / week

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from $226 / 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 large …see more

from $752 / night

$7966 - $10596 / week

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from $752 / night

15

Vacation home in Berrima

Southern Highlands / Berrima

9 26 2 nights min

  • 9 bedrooms
  • Sleeps 26
  • 2 nights min
  • 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 $1036 / night

$7249 / week

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from $1036 / night

4

Bowral Vacation home rental

Southern Highlands / Bowral

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
Book with us through AirBNB! The Cottage - a beautiful and relaxing place to escape and spend time unwinding - comprising 2 good size bedrooms, both with queen beds, a brand new bathroom (including freestanding bath), a comfortable living area with wood-burning firepla …see more

from $158 / night

$1105 / week

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from $158 / 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 $339 / night

$2368 / week

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from $339 / 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 $1159 / night

$5431 / week

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from $1159 / night

18

Bowral Vacation home rental

Southern Highlands / Bowral

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
Only 60 minutes from Sydney Airport Baynton Cottage is a luxurious Southern Highlands retreat set high on the exclusive enclave of Mt Gibraltar, Baynton Cottage is a brilliant retreat offering a classic Southern Highlands experience. With its lush rolling laws and stunn …see more

from $677 / night

$4735 - $6764 / week

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from $677 / night

7

Vacation b&b in Bowral

Southern Highlands / Bowral

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
Relax in a light filled room in the beautiful Southern Highland of Bowral. Your light filled room is located in a very quiet location and is in walking distance to the Bowral main hub. This lovely room has a large screen TV, bar fridge, kettle and toaster with tea and c …see more

from $79 / night

$337 - $467 / week

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from $79 / night

(5) Excellent 

16

Vacation home in Robertson

Southern Highlands / Robertson

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Nearest beach 60 mi
  • Child friendly
  • Air conditioning
Large 4 bedroom house on 7 acres, close to the village of Roberston. House has 2 bedrooms with queen beds and 2 bedrooms each with 2 single beds and two bathrooms. Great location for a quiet break as a couple or with a group of family and friend. Makes an excellent base …see more

from $170 / night

$1128 - $2180 / week

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from $170 / night

18

Home rental in Bowral

Southern Highlands / Bowral

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Air conditioning
  • Private garden
2 good size light filled rooms that join via ensuit. Very private as the main room has it's own front door so you dont have too entre through the main home, there are plantation shutters in both rooms for your privacy. Each room has it's own TV mounted on the wall so y …see more

from $120 / night

$837 / week

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from $120 / night

8

Vacation home in Sutton Forest

Southern Highlands / Sutton Forest

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
Summerlees Cottage is a fully self contained 3 bedroom , 2 bathroom cottage set within the Historical Summerlees Estate. Enjoy 8 acres of private park like gardens on a 70 acre property. Perfect garden wedding location. Winner of the Southern Highlands Business Awards f …see more

from $225 / night

$1420 / week

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from $225 / night

22

Home rental in Sutton Forest

Southern Highlands / Sutton Forest

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Ask about pets
Found in the picturesque town of Sutton Forest this beautiful 125 acre property is a magnificent country retreat. Across the sprawling grounds of the property is the beautiful homestead surrounded by manicured gardens. This seemingly federation style home is the perfect …see more

from $744 / night

$5208 - $9469 / week

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from $744 / night

(2) Excellent 

23

Home rental in Bundanoon

Southern Highlands / Bundanoon

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Car not necessary
  • Air conditioning
  • Private garden
Peaceful, spacious, beautifully renovated house - a short walk from Bundanoon high street but a world away from the city. Lots of room to socialise or to have quiet time; wake to the sound of birds, enjoy the firepit, sit at the "champagne bar", read in front of the log …see more

from $170 / night

$1184 / week

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from $170 / night

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