Vacation rentals in South Windsor

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Top-rated vacation rentals in South Windsor

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

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Guest favorite
Guest suite in Cowan
4.98 out of 5 average rating, 193 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 favorite
A wooden deck extends from the cottage, flanked by lush green foliage and blooming purple flowers. Large glass doors offer a view into the living area, allowing natural light to fill the space. The serene landscape features rolling hills in the distance under a cloudy sky.
Cottage in Kurrajong Heights
4.99 out of 5 average rating, 371 reviews

MontPierre Rustic & Romantic Mountain Cottage

An Immersive Escape šŸFireplace šŸ‚Outdoor Bath šŸ‚Gourmet Services (pre booked) šŸIn-House Therapeutic Massages šŸ‚Valley Views Set on a hilltop, this stylish rustic cottage accommodation offers a unique window into mountain life Inviting for a cosy midweek escape or weekend retreat. Surrounded by trees and local wildlife, the outer village location feels private & laid back, with elevated views. Bush walks close by. The ambiance is relaxed blending comfort, vintage character & rustic charm.

Guest favorite
A spacious deck features comfortable seating arrangements, surrounded by greenery and colorful potted flowers. A view of the expansive landscape and a serene lake is showcased in the background, creating an inviting outdoor space for relaxation.
Cabin in North Richmond
4.94 out of 5 average rating, 232 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 favorite
A cozy fire pit sits in the foreground, surrounded by log stools. The tiny home is visible in the background, its large windows illuminating the dark, serene landscape with a warm glow. Trees frame the scene, enhancing the intimate outdoor atmosphere.
Tiny home in Yellow Rock
4.97 out of 5 average rating, 165 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. Ā  Experience the ā€œtiny homeā€ 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 favorite
A tranquil pool is set against a backdrop of lush greenery and a sunset sky. The still water reflects vibrant hues, while the surrounding deck features a smooth concrete finish. Trees frame the horizon, enhancing the serene environment.
Guesthouse in Ebenezer
4.99 out of 5 average rating, 143 reviews

Quiet country getaway in stylish 2 bdrm shed

There's nothing like a fire in winter! The Shed is a cosy retreat in the Hawkesbury Valley, 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.

Top guest favorite
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, 188 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 favorite
Guest suite in Freemans Reach
4.99 out of 5 average rating, 113 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 favorite
Guesthouse in St Ives
4.99 out of 5 average rating, 138 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.

Guest favorite
A spacious covered deck is presented with wooden flooring and comfortable seating arrangements. Adjoining green lawns and distant views of hills are visible, framed by trees. A table and decorative plants enhance the outdoor atmosphere, inviting relaxation amidst the natural surroundings.
Cottage in Kurrajong Heights
4.99 out of 5 average rating, 249 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!

Guest favorite
A cottage exterior features a spacious wooden verandah, adorned with various seating arrangements. Lush greenery and potted plants frame the entrance, while large windows offer views of the surrounding landscape. A welcoming atmosphere is presented by the simplistic yet stylish design.
Cottage in Grose Vale
4.87 out of 5 average rating, 202 reviews

Grose Vale near Bilpin Tranquil cottage on acres

Sparrow Hall is a stunning cottage with log fire 3 bedrooms on our horse property..14 acres in the Hawkesbury area, 1 hour from Sydney. . Enjoy valley views, a private fenced garden and paddock plus an OUTDOOR BATH! Listen to the bellbirds and feed the horses . Enjoy the outdoor fire pit, bath and stars at night. Explore the lookout in the Blue Mountains, walking tracks and riverside beaches. Fruit picking in Bilpin.. Pet friendly ..with seperate paddock

Guest favorite
Tiny home in Agnes Banks
4.95 out of 5 average rating, 101 reviews

6sixteen The Banks

Welcome to 6SIXTEEN The Banks your peaceful country escape in Richmond, NSW. Set on 5 acres with sweeping views toward the Blue Mountains, this tiny retreat is perfect for couples, solo guests or small families wanting to unwind. Soak under the stars in the wood-fired hot tub, refresh with a cold plunge, or melt into a private infrared sauna session (optional wellness upgrades available). Hosts nearby if needed. Sauna launching Mid March

Top guest favorite
An outdoor hot tub is positioned in the foreground, inviting relaxation. A modern structure with large glass windows reveals a cozy sleeping area featuring a spacious bed and warm bedding. Surrounding trees enhance the natural setting, offering privacy and tranquility.
Farm stay in South Maroota
4.98 out of 5 average rating, 144 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 vacation rentals

  1. Airbnb
  2. Australia
  3. New South Wales
  4. Hawkesbury City Council
  5. South Windsor