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, 178 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

Guest favourite
A spacious gazebo features a wooden table and a natural fiber rug, surrounded by lush greenery. Tall trees rise outside, offering views of the mountains in the distance, with light filtering through the foliage, creating a tranquil outdoor setting.
Home in Upper Colo
4.95 out of 5 average rating, 429 reviews

Laguna Sanctuary

Looking for somewhere to unwind? Nestled in the mountains, this balinese style cottage awaits you! Featuring an outdoor heated spa and views overlooking our freshwater lagoon, you won't regret a weekend here. Relax under the gazebo on our balinese day-bed whilst listening to the native birdlife, enjoy the warmth of our cozy fire-pit area, enjoy a relaxing bike ride or explore the hills with some bushwalking. The options are endless at Laguna Sanctuary.The boathouse cabin is now also available.

Top Guest favourite
Cottage in Kurrajong Heights
4.99 out of 5 average rating, 361 reviews

MontPierre Rustic Cottage-Mountain Hideaway

An Intimate & Rustic, Self-Contained Hilltop Hideaway located on Darug Country, Blue Mountains Designed for relaxation & privacy throughout your stay. The comfortable & cosy 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. Dedicated private & leafy guest courtyard with firepit, vintage outdoor bath tub, and wood-fired pizza oven for an immersive mountain stay

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
Guest suite in Glenbrook
4.97 out of 5 average rating, 121 reviews

Adorable one bedroom studio with outdoor fire pit

Welcome to our cozy, centrally located studio in beautiful Glenbrook. Ideal for couples, families & friends it comfortably sleeps up to four guests. Just a 10-minute walk to Glenbrook village with boutique shops, cosy cafés, a children’s park, and oval. You’re also moments from the Blue Mountains National Park, including local favourites Jellybean & Blue Pool. Enjoy a private stay blending village convenience and outdoor adventure. By booking, you’re supporting our little family thank you 🤍

Top Guest favourite
Tiny home in Yellow Rock
4.97 out of 5 average rating, 151 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, 162 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, 371 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
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, 239 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 fire place 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 before you book & ask about special rates for mid-week!

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
Guesthouse in Saint Ives
4.99 out of 5 average rating, 122 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.

Popular amenities for South Windsor holiday rentals