Holiday houses in South Windsor

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Top-rated holiday rentals in South Windsor

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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
Cabin in North Richmond
4.94 out of 5 average rating, 225 reviews

A Place to be

A place to be says it all, private property with large gums Placing the cabin underneat the tree tops overlooking a large lake Bird feeders for the wildlife and horses waiting at the gate Most of all this cabin is quite and suits couples looking for relaxing time A self contained space For a special someone or just yourself Beautiful big 4 poster bed Overlooking acres Horses and kookaburras await there treats This place is special. a hot bath for two people on-the deck is perfect to relax

Top Guest favourite
Cottage in Kurrajong Heights
4.99 out of 5 average rating, 362 reviews

MontPierre Rustic Mountain Cottage -Wood Fireplace

A Cosy & Rustic, Self-Contained Hilltop Hideaway located on Darug Country, Blue Mountains Designed for relaxation & privacy throughout your stay. The comfortable & charming accomodation is tailored to romantic, relaxing escapes or a peaceful getaway for two close friends to enjoy a quiet catch up Enjoy the eclectic rustic interiors & indoor fireplace. Private & leafy guest courtyard with firepit, vintage outdoor bath tub, and wood-fired pizza oven for an authentic rustic mountain stay.

Top Guest favourite
Tiny home in Yellow Rock
4.97 out of 5 average rating, 154 reviews

Tiny Bush Escape Blue Mountains

Private Adults-Only Tiny Home | Bush Escape | 1.5hrs from Sydney Looking to truly unwind? This peaceful retreat is tucked away among the trees in the lower Blue Mountains – the perfect spot to slow down, reconnect with nature, and exhale.   Experience the “tiny home” lifestyle in what was once a 40ft shipping container. This beautiful tiny home has been thoughtfully transformed into a luxurious escape for couples, solo travellers, or close friends looking to recharge in privacy and comfort

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

Top Guest favourite
A tiny home is viewed from the outside, showcasing large windows that provide a glimpse of the interior space. Natural wood accents and a small deck area enhance the inviting atmosphere, while surrounding greenery complements the structure.
Tiny home in Wheeny Creek
4.96 out of 5 average rating, 100 reviews

Tiny Love Getaways

Welcome to Tinylove Getaways our tinyhome is located in the beautiful Colo River Valley. With Spa bath , firepit area , in a private bush setting its perfect for a couple looking to relax and unwind. With friendly farm animals including our 4 mini donkeys who love to pop in and greet our guests. Fully self contained with all you need and only 20 mins drive to closest shops and restaurants. Great for a winter escape or a Summer getaway with the colo river only a short distance away.

Top Guest favourite
A spacious living area features a dark leather sofa with decorative pillows, complemented by a cozy electric fireplace. The room is adorned with a large artwork of a Highland cow and accented by a light area rug. A brown wooden console table adds elegance.
Guest suite in Freemans Reach
4.99 out of 5 average rating, 106 reviews

Studio 135 & Hot tub Freemans Reach NSW Australia

Studio 135 Freemans Reach offers a romantic getaway whilst capturing the charm of historic Windsor and showcasing some of Hawkesbury's historic homesites. The tranquil, rural setting can also be enjoyed from the rear with a furnished patio and a 2 person hot tub. The spacious studio has two living spaces and comes fully self contained and is set on 1/2 an acre of parklike grounds surrounded by larger acres and is situated close to Historic Windsor, Wilberforce and Richmond.

Top Guest favourite
An exterior view of a modern cottage showcases a green metal roof and a wooden facade. Lush trees surround the property, with expansive views of rolling hills and the valley in the background under a clear blue sky.
Cottage in Kurrajong Heights
4.99 out of 5 average rating, 240 reviews

SKY FARM - mid week deals

Luxury in the countryside with big city views. This stylish cottage & sunny deck will reconnect you with nature in no time. Bilpin is just up the road with organic markets, cellar doors & "pick your own" fruit farms. Views from the deep bath are stunning & the cosy fireplace is fully stocked with everything you need. Snuggle up at the outdoor fire pit under a big sky. If you need convincing just read the reviews! Enquire prior to booking for special mid-week deals!

Superhost
A cozy sleeping area features a spacious bed adorned with soft pillows and a textured throw. A stylish black lamp illuminates the space, complemented by sloped wooden ceilings and a soft green plant, bringing a serene touch to the room.
Religious building in Kurrajong Heights
4.93 out of 5 average rating, 185 reviews

Beautiful old Church built 1889 and restored

Enjoy the tranquil gardens and the relaxing atmosphere inside and outside the Church. This will be an experience you will never forget. This unique Church has been restored beautifully and is a place to relax and unwind. It is close to local shops, the famous Grumpy Baker, restaurants such as the Lochiel House and an Indian Restaurant, fruit picking from January to June, Cellars doors with local apple cider and much more. It is truly unique.

Top 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.

Top Guest favourite
A private outdoor entrance features a paved area with potted plants and vibrant flowers. Two striped chairs are positioned on either side, while a large covered deck is visible in the background, furnished with a dining table and chairs under a lattice overhead.
Guest suite in Springwood
4.98 out of 5 average rating, 194 reviews

Poetsridge Escape

NO CLEANING FEE & MULTI NIGHT DISCOUNTS. Please read the additional house rules before booking. Large private guest suite with own entrance. Spacious, peaceful and tastefully decorated. Modern bathroom with laundry facilities, kitchenette and large lounge area. Magnificent bushland views from the pergola. See pictures for floorplan. Just 3km from Springwood Village. No Smoking. Sorry our property is not suitable for children of any age.

Popular amenities for South Windsor holiday rentals