Holiday houses in South Windsor

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Top-rated holiday rentals in South Windsor

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Top Guest favourite
A spacious bush retreat is surrounded by tall trees and a well-maintained lawn, providing a serene setting. The architecture features a combination of light and dark elements, with multiple rooflines and a welcoming façade visible under a clear blue sky.
Guest suite in Grose Wold
4.94 out of 5 average rating, 151 reviews

"Moonlight Ridge" Hawkesbury Guesthouse

Luxurious B&B bush retreat, located 1-hour NW of Sydney at the foot of the beautiful Blue Mountains. Enjoy the fully private space: Queen bedroom, kitchen, fireplace in winter, coffee machine, bathroom, lounge room, TV, A/C, additional living space & access to our gardens with your own private gazebo. COMPLIMENTARY BOTTLE OF WINE WITH EVERY BOOKING! Come & relax in a tranquil country setting, surrounded by majestic trees & bird calls. The perfect base to explore the Hawkesbury & Blue Mountains.

Guest favourite
The living area is characterized by large glass doors opening to a scenic view, allowing natural light to fill the space. A comfortable seating arrangement is present, with a soft blanket draped over a couch. A dining table and rustic shelves are located in the foreground.
Guest suite in Cowan
4.98 out of 5 average rating, 180 reviews

The Lotus Pod - Unique Guesthouse with views

Situated in the grounds of Austral Watergardens nursery, this large,spacious studio is located approx. 50 mins drive north of Sydney. On the doorstep of the Hawkesbury River and Berowra Waters, the Lotus Pod offers a country escape or romantic getaway. With magnificent views across the pristine Mougamarra Nature Reserve and surrounding gardens, a perfect place to relax & unwind. Visit the local eateries, enjoy fresh seafood on the River, Ferry Rides, The Great North walk & bushland scenery

Top Guest favourite
A private balcony offers outdoor dining with a table set for two, accompanied by vibrant views of the water and distant city skyline. Lush greenery frames the scene, while tranquil blue waters reflect the clear sky.
Condo in Mosman
4.98 out of 5 average rating, 190 reviews

Absolute Harbourfront Apartment with Fabulous Panoramic Views

Magnificent piece of paradise at the waters' edge. Heart stopping views from every room (Guest 2017) Bright & sunny, idyllic waterfront sanctuary Separate home office All linens and unit professionally cleaned Alfresco balcony perfect for drinks/meals BBQ dining, sun lounges, harbour pool Onsite parking: max. car height 1.7 metres Bus & ferry close Fireworks often seen, spectacular on New Year's Eve & Australia Day Peaceful by day, stunning by night Come and chill out – you won't want to leave!

Guest favourite
A country cabin is positioned amid a grassy landscape, surrounded by trees. The exterior features large windows and a wooden porch with seating. Cows graze peacefully in front of the cabin, and a clear blue sky serves as a backdrop.
Place to stay in Kurrajong
4.71 out of 5 average rating, 196 reviews

Kurrajong Country Cabin Seperate from main home

Need a country escape??? Need a place to relax and unwind? No phone, no tv ,no distractions, just sit back and enjoy listening to nature! Our country cabin is located on acerage in the little suburb of Kurrajong a 4 minute drive to kurrajong village. It is seperate from the main house, it does not have kitchen facilities, however we offer a selection of teas, coffee, toaster and kettle. There is a list of local cafes , convenience store, local restaurants a 4 min drive from our Cabin.

Top Guest favourite
The exterior of the cabin is showcased with rustic corrugated metal siding and wooden accents. A porch with potted plants and firewood is visible, while greenery surrounds the area. Sunlight brightens the scene, highlighting the cabin's charming country-style architecture.
Cabin in Kurrajong Hills
5 out of 5 average rating, 177 reviews

The Milking Shed

The Milking Shed is a cosy cabin in the lush green hills and beautiful vistas of the Hawkesbury region north-west of Sydney. The cabin is built on the side of a hill and looks directly into a small forest of eucalypts - perfect for trying to spot one of our regular koala visitors. It is 200m past the main house on the property, and completely private. Curl up with a book, feed a donkey, pour a wine, cuddle a corgi, or sit on the deck take in the country. It is a million miles from care.

Top Guest favourite
A modern, single-story cabin is surrounded by natural woods. A wooden deck extends from the entrance, with outdoor seating and a barbecue area visible. Graveled pathways lead to distinct seating arrangements, featuring two light-colored chairs and a wooden table, enhancing the tranquility of the setting.
Tiny home in Sackville North
4.98 out of 5 average rating, 163 reviews

Villa 37 Tiny Home Experience

Reconnect with nature at this unforgettable escape. Just a short drive from Sydney in the rural outskirts of the Hills District, this beautiful location speaks for itself with endless views of the Hawkesbury River across to the Blue Mountains. Villa 37 is fully self contained with split air conditioning, a kitchenette featuring convection microwave, refrigerator, benchtop hotplate, cooking equipment, excellent bathroom facilities along with two outdoor bathtubs with spectacular views.

Top Guest favourite
A calm river scene captures the reflection of lush green hills and scattered trees along the riverbank. A hint of red foliage adds a splash of color amid the greenery. The still water mirrors the serene landscape, creating a peaceful atmosphere.
Cottage in Lower Portland
4.96 out of 5 average rating, 373 reviews

Carina Cottage

Freshly renovated, PRIVATE and absolute waterfront Cabin with all amenities overlooking the most magnificent section of the Hawkesbury River at Lower Portland (City side of the River) - there is a modest (but modern) kitchen - adjacent to bushland teeming with bird life and rural properties nearby historic Hawkesbury sites and wineries with pretty walks along the River and fire trails 90 mins from Sydney CBD 30 mins from Windsor and Glenorie 40 mins from Rouse Hill and Castle hill

Guest favourite
A cabin is nestled within a lush green landscape, surrounded by tall trees and a well-maintained lawn. A spacious outdoor area can be seen leading to the house, which features a glass-enclosed porch, enhancing the connection to the natural surroundings.
Cabin in Mountain Lagoon
4.93 out of 5 average rating, 252 reviews

Scrumpy Hollow - Peaceful Cabin in National Park

Scrumpy Hollow is a peaceful cabin getaway in the Blue Mountains suitable for family holiday breaks or romantic getaways. Located in the Wollemi National Park in the Blue Mountains & within easy reach of Sydney, 'Scrumpy' has 3 bedrooms with 1 King Size, 1 Queen size & 2 single beds & comes complete with modern conveniences such as a fully equipped kitchen & free wi-fi. Ideally placed to use as a base for walking, exploring, or enjoying the peace, Scrumpy has something for everyone.

Top Guest favourite
A covered outdoor area features two wicker chairs set on a wood deck, inviting relaxation. A view into the interior reveals a spacious dining table surrounded by modern chairs, illuminated by soft overhead lighting.
Guest suite in Wahroonga
4.98 out of 5 average rating, 168 reviews

Rainforest Tri-level Townhouse.

Enjoy a peaceful stay in this updated tri-level townhouse, among leafy, tree-lined streets. With its own separate access, off-street parking, and ample safe street parking available, this home offers privacy and convenience. Perfectly located just off the M1 motorway, it’s an ideal stopover along the M1, while also being close to the SAN Hospital, major schools and shopping. Nearby parks, an oval, and bush walks add to the tranquil setting, an ideal base for short or longer stays.

Top Guest favourite
Guesthouse in St Ives
4.99 out of 5 average rating, 124 reviews

Luxury Garden Cottage Retreat - Romantic & Restful

Arriving through antique gates, wander down wisteria covered walkway to your home away from home. Outdoor tiled undercover area with dining/living space, lit in evenings with silk lanterns invite you outside for a special occasion. Light-filled cottage, open plan living/dining area. Bedroom boasts plush queen bed for a blissful nights' sleep. Bathroom invites indulgence with a rainforest shower. Fully equipped kitchen with washing machine. Thoughtful touches throughout.

Top Guest favourite
The lounge area features comfortable seating on a light-colored sofa, with vibrant pillows adding a pop of color. A coffee table filled with books sits in the center, while sunlight streams in through large windows, illuminating the greenery outside.
Condo in Mosman
4.91 out of 5 average rating, 108 reviews

MOSMAN - lovely art apartment.

Mosman - one of Sydneys finest suburbs. Beautiful Bright Art Apartment, Master Queen size large bedroom and a lovely Double bedroom. Mosman Ferry 600 metres to city. Cafes and local shops 100 metres from front door. Luxury boutiques 600 metres to gorgeous strip shopping plus a lovely walk to Mosman Zoo, famous Orpheum Cinema and Balmoral Beach and its restaurants Bus at front door. Balmoral beach 10 minutes away. The gateway to the northern beaches. Perfect location.

Guest favourite
A modern cabin is set among trees, with large windows that offer views of the natural surroundings. A gravel area in front features a small fire pit surrounded by stones. Soft lighting enhances the peaceful outdoor setting.
Farm stay in South Maroota
4.98 out of 5 average rating, 132 reviews

Soulful Wilderness Cabin "Countryside 100" kingbed

This purpose-built small space is perched in the prettiest spot on a private 25 acre property. With stunning views, an inviting outdoor hot tub and luxurious furnishings, you won’t want to leave. Nurture your soul & pare back to nature with a splash of luxury & comfort. With all the mod cons you could wish for & strategically placed in the most peaceful natural setting you could imagine. Easy access, drive to the front door, no 4WD required.

Popular amenities for South Windsor holiday rentals