Vacation rentals in South Windsor

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Top-rated vacation rentals in South Windsor

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Top guest favorite

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, 143 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.

Top guest favorite

A spacious living area features a comfortable sofa adorned with cushions. A coffee table sits on a textured rug, with a wood heater surrounded by a safety gate. A dining table is visible in the background, complemented by tasteful lighting and modern kitchen amenities.

Guesthouse in Ebenezer

4.98 out of 5 average rating, 122 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.

Top guest favorite

A welcoming entrance leads into a cozy cottage, framed by lush greenery. Light filters through a large window, illuminating the inviting interior space. Potted plants are placed along the entrance, enhancing the natural ambiance.

Cottage in Kurrajong Heights

4.99 out of 5 average rating, 339 reviews

MontPierre Rustic & Cosy Mountain Cottage

Experience a window into mountain life in this ‘romantic rustic hilltop escape’ boasting garden views below & valley views beyond Surrounded by trees & wildlife, the outlook is nature in abundance The vibe is casual comfort The property is rustic panache The location is green & tranquil Enjoy the simplicity of log fires, outdoor vintage bath, vintage records, & wood fired pizza We offer several in-house services if you wish to elevate your stay with options of rejuvenation or adventure.

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, 126 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 favorite

A dining area is set on a spacious deck, featuring a glass table surrounded by three chairs. Decorated with candles and flowers, the table offers a view of the lush landscape beyond, with greenery and trees visible in the background under a clear blue sky.

Guest suite in North Richmond

4.92 out of 5 average rating, 436 reviews

Amazing view

This is an entire unit that is attached to our home but it has its own front and back doors. This is an excellent spot for bird viewing and walks along the Hawkesbury River. It is within walking distance of coffee shops, restaurants, and a 24-hour gym. Take trips to The Blue Mountain Botanical Gardens (37km). Ebenezer Church (17 km). Bellbird Hill Lookout. Windsor Mall Sunday Markets. Balloon Rides. Convict Trail. Australiana Pioneer Village (15km). Hawkesbury regional gallery.

Top guest favorite

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, 218 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, cider cellar doors & pick your own fruit. Views from the deep bath are stunning & the cosy fire place is fully stocked. Relax at the outdoor fire pit under a big sky. A breathtaking retreat..... if you need convincing just read the reviews. Enquire before you book to get a great mid-week special rate!

Superhost

A charming pink door with glass panels is framed by a brick wall. A small green plant is positioned beside the door, and a screen door is visible, offering a glimpse into the entrance's welcoming design.

Home in Windsor

4.89 out of 5 average rating, 38 reviews

No28 - 99 years in the heart of Windsor

No28 is a home away from home, centrally located in the heart of Windsor. Being 99 years old, this property has seen a lot in its years and continues to impress with art deco design and a spacious closed in back yard and veranda. Simple yet beautiful, our aim is to provide a comfortable space that works for couples, families or friends wanting to relax, watch dvds, read, play games or explore the local area. Close to shops and amazing restaurants, galleries, and cafes.

Top guest favorite

A historic cottage is presented with a welcoming façade featuring a white picket fence and a covered porch. Lush green grass surrounds the home, while trees provide shade in the background. The metal roof emphasizes the property's classic charm, blending seamlessly with its heritage-style design.

Home in Windsor

5 out of 5 average rating, 17 reviews

Secret River Cottage - History in Windsor

Discover Secret River Cottage, a beautifully appointed historic cottage perfect for travelers and business visitors alike. Nestled in Windsor, Australia, this heritage-listed home, built in 1838, combines charming period details with modern comforts. Just a stone's throw from Windsor's Town center and the serene Hawkesbury River, it offers the best of both worlds. Enjoy the convenience of air conditioning, a cozy log fire, and off-street parking for two cars.

Guest favorite

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, 110 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 favorite

Three friendly alpacas are visible in a lush green field, with one light-colored and two darker alpacas. The background features a charming house and trees, set against a tranquil hillside landscape.

Farm stay in Kurrajong

4.97 out of 5 average rating, 159 reviews

Lavender House and Alpaca Farm

Lavender House is an alpaca farm in Kurrajong. With splendid views of the Blue Mountains it is a fantastic place to relax and enjoy a quieter pace of life. The cafes and coffee shops of the quaint village of Kurrajong are 5 minutes away. Your hosts live on the top floor of the large two storey home with your self contained apartment with all facilities taking up the bottom floor. The alpacas are very friendly and love to be fed by hand.

Top guest favorite

The front of the cottage features a welcoming facade with a central door framed by two windows. Neatly trimmed grass is seen, complemented by decorative planters on either side containing small trees and vibrant plants.

Home in Windsor

4.96 out of 5 average rating, 23 reviews

1840s Heritage house in Windsor

Heritage listed 1840s cottage in Windsor. Close to cafes, parks and the Hawkesbury river whilst still peaceful and private. Stay cosy with full zone controlled ducted heating/cooling. Spacious king room and a separate bedroom with twin single beds. The house retains charming original features including a working open fire place. Includes a modern, well equipped kitchen and dining space. Relax in the sunny private courtyard.

Superhost

A cozy tiny home is positioned amid lush greenery, featuring large windows that invite natural light. A wooden deck offers a relaxed seating area with two chairs, while a stone fire pit surrounded by logs provides a warm gathering space outdoors.

Home in Freemans Reach

4.81 out of 5 average rating, 103 reviews

Malniri Park by Tiny Away

Plan your next weekend getaways in Malniri Park by Tiny Away, North-West of Sydney. This tiny home is the perfect holiday home for families set high on a private plateau with stunning views overlooking the equine working farm and the fertile lowlands of the Hawkesbury River. It is a thoroughbred horse farm for pre-training and horse agistment and has been operating in the Hawkesbury area for more than 40 years.