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

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Apartments Bowral
8 properties
Robertson
6 properties
Berrima
5 properties

Southern Highlands

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79 Vacation rentals

(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 $373 / night

$2,085 / week

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Responds fast!
avg. 3 hours 53 minutes

from $373 / night

(2) 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 $261 / night

$1,861 / week

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Responds fast!
avg. 28 minutes

from $261 / night

(5) 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 $222 / night

$1,117 - $1,690 / week

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Responds fast!
avg. 3 hours 19 minutes

from $222 / night

14

Vacation home in Burrawang

Southern Highlands / Burrawang

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 50 mi
  • Child friendly
  • Air conditioning
Sirmione is a beautiful, large 4 bedroom and 3 bathroom, modern homestead style house. Surrounded by stunning landscaped gardens, the house sleeps 8 with facilities to accommodate 2 extra guests. It has 3 large bathroom, 2 en suite and one with a bath. There are two la …see more

from $409 / night

$2,857 / week

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from $409 / 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 $373 / night

$2,606 / week

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from $373 / night

12

Robertson Vacation home rental

Southern Highlands / Robertson

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Private garden
Laurel View is a working farm running beef and lamb which is sold directly through our own butcher shop, Maugers Meats. The farm house is surrounded by stunning views of the countryside and paddocks dotted with cattle and sheep. It is a quick trip to Burrawang for lunc …see more

from $306 / night

$1,787 / week

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from $306 / night

(8) Excellent 

12

Vacation apartment in Exeter

Southern Highlands / Exeter

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
Set on a beautiful 140 acres just outside the village of Exeter in the heart of the NSW Southern Highlands, this elegantly presented farmhouse, garden and property provides guests with a perfect country getaway just 2 hours from Sydney. Two bedrooms can accommodate two …see more

from $186 / night

$1,303 / week

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from $186 / night

18

Vacation home in Robertson

Southern Highlands / Robertson

4 10 2 nights min

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min
  • 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 $325 / night

$2,581 - $3,097 / week

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avg. 3 hours 32 minutes

from $325 / night

(3) 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 $365 / night

$2,554 / week

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from $365 / night

18

Vacation home rental

Southern Highlands / Canyonleigh

4 12 2 nights min

  • 4 bedrooms
  • Sleeps 12
  • 2 nights min
  • Child friendly
  • Private garden
Thinking of a holiday with families and friends in a private and charming farm house, enjoying the never-same sunrise, sunset and mountain view from your own bedroom windows and a cup of tea while overlooking the flowery backyard? Or want a dream country style celebrati …see more

from $222 / night

$1,553 / week

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from $222 / night

(2) Excellent 

16

Vacation home with swimming pool in Berrima

Southern Highlands / Berrima

14 50 1 night min

  • 14 bedrooms
  • Sleeps 50
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Sleeping 28 standard comfortably without the need for roll aways or sofa beds, or optionally 55 guests in other rooms with King Beds, King singles, bunks etc. Berrima Retreat provides premier self-contained accommodation for large groups. Berrima Retreat makes a great b …see more

from $2,044 / night

$7,081 - $18,322 / week

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Responds fast!
avg. 3 hours 46 minutes

from $2,044 / night

(5) Excellent 

55

Cottage rental in Berrima

Southern Highlands / Berrima

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 41 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 $224 / night

$1,564 / week

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Responds fast!
avg. 14 minutes

from $224 / night

(4) Excellent 

7

Vacation barn in Berrima

Southern Highlands / Berrima

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • 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 $626 / night

$3,722 / week

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from $626 / night

27

Robertson Vacation home rental

Southern Highlands / Robertson

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Luxury Country Retreat is a perfect place for a family holiday near Sydney, locate at Robertson Southern Highland. Just one and half hours drive away from Sydney, not far off the main road to Robertson, down a little country lane, you will arrive at Luxury Country Retr …see more

from $633 / night

$4,429 / week

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Responds fast!
avg. 44 minutes

from $633 / 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 $1,303 / night

$9,119 / week

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from $1,303 / night

27

Vacation home in Robertson

Southern Highlands / Robertson

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Private garden
At In2thewild we provide brand new Luxury Tiny Houses in completely secluded off-grid locations offering you a chance to completely disconnect and relax under 2 hours from Sydney. Sleep up to 4 with a loft bed upstairs and two convertible couch / single beds downstairs. …see more

from $163 / night

$1,142 / week

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from $163 / night

16

Vacation home with golf nearby in Bowral

Southern Highlands / Bowral

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • 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 $894 / night

$4,764 - $7,891 / week

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from $894 / night

(1) Excellent 

10

Vacation home in Berrima

Southern Highlands / Berrima

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
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 $1,229 / night

$6,878 - $8,114 / week

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from $1,229 / night

(2) Excellent 

14

Canyonleigh Vacation home rental

Southern Highlands / Canyonleigh

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Your retreat is brand new, self-contained, luxurious, and is the perfect weekend or mid-week getaway in a secluded country setting. Picnic amongst the eucalypt and pine trees, or wander along the 2km stretch of the beautiful Wollondilly River. Only 1.5 hours from Sydn …see more

from $193 / night

$1,351 / week

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from $193 / night

(6) 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 $209 / night

$1,459 / week

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from $209 / night

17

Vacation home in Bowral

Southern Highlands / Bowral

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
Our newly renovated, 100 year old weatherboard cottage lies close to the hub of Bowral, with its many restaurants, cafés and boutiques, and its gorgeous parks, museums, galleries, vineyards and golf courses. My place is both intimate and elegant, and is perfect for a ro …see more

from $146 / night

$1,191 / week

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from $146 / night

(7) Excellent 

4

Vacation cottage in Fitzroy Falls

Southern Highlands / Fitzroy Falls

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
Escape the city with a relaxing rustic adventure at Redleaf Carriage343. Built in 1890 as a NSW Railways Guards Van, converted to freight guard and passenger transport in the 1930, abandoned in late 1970's and now lovingly restored to accommodate farm stay guests at R …see more

from $246 / night

$1,720 / week

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from $246 / night

51

Vacation home in Berrima

Southern Highlands / Berrima

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 43 mi
  • Child friendly
  • Air conditioning
A beautiful luxurious COUNTRY HOUSE set in the heart of Historic Berrima moments away from all the amenities this village has to offer. Located close to many of the Southern Highlands wedding venues, golf courses and wineries. A great multi generational home to gather w …see more

from $447 / night

$3,127 / week

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Responds fast!
avg. 14 minutes

from $447 / 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 $167 / night

$1,114 - $2,152 / week

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from $167 / 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

$335 - $466 / week

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Responds fast!
avg. 2 hours 36 minutes

from $79 / night

(1) Very Good 

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 $119 / night

$834 / week

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Responds fast!
avg. 2 hours 36 minutes

from $119 / 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 $224 / night

$1,415 / week

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from $224 / 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 $737 / night

$5,159 - $9,379 / week

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from $737 / 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 $670 / night

$4,690 - $6,700 / week

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from $670 / night

24

Vacation home in Bundanoon

Southern Highlands / Bundanoon

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
Escape for a weekend to Springfield Farm in Bundanoon, Southern Highlands. A farmhouse with old-world charm merely two hours drive from Sydney. Springfield Farm is a five bedroom house located on a stunning 170 acre country estate with four bathrooms and spacious living …see more

from $742 / night

$5,195 - $7,792 / week

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from $742 / night