Holiday houses in South Windsor

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Top-rated holiday rentals in South Windsor

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Guesthouse in Ebenezer
4.99 out of 5 average rating, 139 reviews

Quiet country getaway in stylish 2 bdrm shed

Whisk your loved ones away to this cosy retreat in the Hawkesbury Valley. The Shed is a charmingly converted workshed offering plush beds, a rustic kitchen, comfy lounge area, wood heater, and an outdoor firepit perfect for stargazing. Enjoy Netflix, Wi-Fi, stunning sunsets, and gentle visits from kangaroos, alpacas, and native birds. A peaceful haven for two or a small family—and yes, your pup can come too! Hearty breakfast provisions supplied, including freshly homebaked sourdough on arrival.

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, 430 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
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 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. 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, 152 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
The large house is set against a backdrop of lush greenery and autumn foliage. A spacious lawn stretches in front, with a covered porch offering seating. The area features a mixture of sunlight and shadows, enhancing the peaceful outdoor setting.
Home in Bilpin
4.98 out of 5 average rating, 103 reviews

True North - 4BR Bilpin Bush Retreat

True North is a large, rustic house in Bilpin (Blue Mountains), famous for its apple picking and ciders. The house has 4 bedrooms for up to 8 guests and surrounded by country gardens, green lawn and plenty of wildlife filled trees. If you love being outside you'll love the large swimming dam and cozy outdoor firepit area! The home features thoughtfully furnished bedrooms, quality linen, aircon, indoor and outdoor fireplace, large fully equipped kitchen, family dining area and a sunroom.

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
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 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
A spacious bedroom features a queen bed adorned with a textured yellow throw and decorative pillows. Light wood furniture includes bedside tables with lamps. A mirror wardrobe reflects natural light, while a cozy lounge area is visible in the background, enhancing the room's inviting appeal.
Guest suite in Bella Vista
4.92 out of 5 average rating, 144 reviews

Corporate Hide-Away/5mins walk to Norwest Metro.

Attached to existing home, with two separate entrances (front & back) into the flat. A 5min walk to Norwest Shops, bus stops, HillSong Church & the Metro train system connecting you to the City in under 30 minutes! 10 minutes drive from Bella Vista & Baulkham Hills Private Hospitals & Lakeside Medical Rooms. Surrounded by Norwest Business Park! Perfect for corporate renter, holidayers, weekend & mid-week use or week2week accommodation. Private, safe & tastefully decorated.

Top Guest favourite
Guesthouse in St Ives
4.99 out of 5 average rating, 123 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.

Superhost
The exterior of the residence is showcased with manicured lawns and various shrubs. Lush trees are visible in the background under a partly cloudy sky. The driveway leads towards the entrance, flanked by neatly trimmed hedges and colorful flower beds.
Home in Kurrajong
4.88 out of 5 average rating, 267 reviews

Kurrajong Accommodation

Chalet de Tranquillité is a eclectically styled private residence with modern facilities that offers affordable year round accommodation WITH NO CLEANING FEES, for families, friends and executives. Comes fully equipped and is the perfect haven for that escape to the country and, is within walking distance to local shops, cafes, restaurants. supermarket. We are ideally located to all wedding venues ,within 30 minutes from the botanical gardens at Mt Tomah

Popular amenities for South Windsor holiday rentals