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Southern Highlands House Rentals

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    Southern Highlands is popular with travellers just like you. Don’t let them get your perfect place first—book today!
    25 Matching Rentals in Southern HighlandsView all 32 rentals
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    Bluebird Escape, Southern Highlands1 / 31
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Stately Bowral Designer Home1 / 32
    (3)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Berrima Retreat Luxury Group Accommodation from $49pp1 / 16
    (2)Excellent
    14 Bedrooms, 4 Bathrooms, Sleeps 50 Quick View
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    Garden Keepers Cottage1 / 11
    (5)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Mountain Views
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 November 2017
    Great and charming little cottage with everything you could want, including coffee and wine and electric blankets for the not so hot weather and a warm and flexible welcome by...
    Reviewed 15 August 2017
    thanks to Jan for our stay at the Gate Keepers, it was a perfect sunny afternoon on the terrace sheltered by the garden for book reading lunch & dozing in the winter...
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    About this property
    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 mention a Chemist and Medical Centre...
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    Bowral, Southern Highlands 2576
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Private Garden
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 lunch or a drink at the Burrawang...
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    Robertson, Southern Highlands 2577
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Patio
    • Parking
    • Central Heating
    • Grill
    • Balcony
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 celebration outside of the city noise?...
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    Canyonleigh, Southern Highlands 2577
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Central Heating
    • Balcony
    • Washer
    • Housekeeping Included
    • Terrace
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 home set on 100 acres of...
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    Robertson, Southern Highlands 2577
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Sassafras House, a quiet country retreat for the extended family or large group1 / 16
    (2)Excellent
    5 Bedrooms, 2 Bathrooms, Sleeps 16 Quick View
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    • Parking
    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 March 2018
    perfect for our extended family and soo many toys for the kids.we all really appreciated the cleanliness and comforts .Thank you very much Jess
    Reviewed 9 March 2017
    We loved our girls stay at Sassafras! It was such a beautiful, quiet spot with an immaculate garden. The house was spotless and had everything we needed. It's deceivingly big...
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    About this property
    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 having to pack half the house...
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    Robertson, Southern Highlands 2577
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 16
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    Sirmione – a gorgeous country house in the stunning NSW Southern Highlands.1 / 13
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Garden
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    We had a great stay at this house with our friends for a Christmas in July weekend. It was the perfect size for 6 adults, 4 children and a baby with lots of different areas to...
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    About this property
    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 large family living areas each...
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    Burrawang, Southern Highlands 2577
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    The Retreat at Robertson1 / 16
    (5)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Outdoor Dining Area
    • Air Conditioning
    • Shared Garden
    • Washer
    • DVD Player
    • Terrace
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 June 2015
    My dealings with the owner (Kim) were delightful. The 'Retreat' felt like home, except more luxurious! It was comfortable, relaxing and very cosy. The garden and surroundings...
    Reviewed 25 May 2014
    I have been going down to "the retreat at roberstson" for quite a while now, and every time I feel so much joy when I'm there.It has a real sense of magic...so seculded...
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    About this property
    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 to explore the Southern...
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    Location Information
    Robertson, Southern Highlands 2577
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    7 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • Grill
    • DVD Player
    • Terrace
    • Central Heating
    • Washer
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 enjoy the fresh country air....
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    Southern Highlands, New South Wales 2622
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 20
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Parking
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 stunning formal gardens, this is...
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    Location Information
    Bowral, Southern Highlands 2576
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Private Garden
    • Air Conditioning
    • Grill
    • Secure Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 Retreat and its private tree...
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    Robertson, Southern Highlands 2577
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Light filled rooms1 / 17
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Parking
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 October 2017
    We really enjoyed our stay at Danna's B&B. It's 5 minutes drive from the main Bowral streets, quite and quite spacious. D had provided fruits, variety of cereals, sourdough...
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    About this property
    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 you can lay back in bed and...
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    Bowral, Southern Highlands 2576
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 and dining areas. It is the...
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    Location Information
    Bundanoon, Southern Highlands 2578
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Central Heating
    • Washer
    • Housekeeping Included
    • DVD Player
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 Cinema and boutique shops....
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    Location Information
    Bowral, Southern Highlands 2576
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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. Looking for a beautiful and...
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    Robertson, Southern Highlands 2577
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Dixieland Estate1 / 10
    (1)Excellent
    8 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Cable/satellite TV
    • Secure Parking
    • Patio
    • Air Conditioning
    • Washer
    • Balcony
    • Terrace
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 June 2017
    This house is truly wonderful and the photos do not do it justice. We were a family of 19 and it was so perfect. The lounge room Was massive and the the dining areas and kitchen...
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    About this property
    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 Estate is a magnificent 27-acre...
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    Berrima, Southern Highlands 2577
    Holiday Rental House - 8 Bedrooms, 5 Bathrooms, Sleeps 16
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    Arcadian Cabin Canyonleigh - Southern Highlands River Retreat1 / 14
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Housekeeping Included
    • Terrace
    • DVD Player
    • Grill
    • Patio
    • Parking
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 January 2018
    Comfortable well equipped cabin with everything we needed for our little ones. Beautiful, serene and peaceful setting. Nothing like watching the sunset with kangaroos grazing...
    Reviewed 6 January 2018
    Our family of four with kids aged 5 and 8 stayed in this comfy cabin in Canyonleigh. The cabin is very comfortable - 2 bedrooms, comfortable beds and bedding (all new), TV + DVD...
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    About this property
    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 Sydney or Canberra, and 30...
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    Location Information
    Canyonleigh, Southern Highlands 2577
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Berrima, Southern Highlands 2577
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 romantic weekend away, or for a...
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    Bowral, Southern Highlands 2576
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 for Excellence in...
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    Sutton Forest, Southern Highlands 2577
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Terrace
    • Secure Parking
    • Grill
    • Balcony
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 with your family or large...
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    Berrima, Southern Highlands 2577
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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, Mirriyindi is the perfect getaway for small families or couples. 'Pay for 2, stay for...
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    Berrima, Southern Highlands 2577
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
    • Air Conditioning
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Berrima, Southern Highlands 2577
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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