Vacation rentals in South Windsor

Guest suite in Grose Wold

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.

4.94 out of 5 average rating, 145 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.

Guest suite in Freemans Reach

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.

4.99 out of 5 average rating, 92 reviews

Studio 135 & Hot tub Freemans Reach NSW Australia

Studio 135 Freemans Reach offers a romantic getaway and a little piece of heaven on earth. The Studio's decor captures the charm of historic Windsor whilst 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 studio which comes fully self contained is set on 1/2 an acre of parklike grounds surrounded by larger acres and is situated close to Historic Windsor, Wilberforce and Richmond.

4.97 out of 5 average rating, 130 reviews

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

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

4.81 out of 5 average rating, 525 reviews

A modern living area is furnished with a blue sofa and two patterned armchairs. A glass coffee table sits on a textured rug, surrounded by natural light. The kitchen is visible in the background, showcasing white cabinetry and a seating area with bar stools.

Townhouse in Bella Vista

Modern & Spacious Granny Flat in Bella Vista

RIGHT IN THE HEART OF BELLA VISTA ! Well-lit & modern 1 bedroom granny flat with spacious kitchen and bedroom. Has separate side entry from main house so guests have full privacy. Kitchen with white goods and cooking utensils. Equipped with air con and Wi-Fi. Has courtyard seating outside. Living room with sofa bed and TV. Comfortable queen bed in bedroom with en-suite bathroom attached. Convenient location close to Norwest business park and walking distance to public transport!

Guest suite in North Richmond

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.

4.92 out of 5 average rating, 439 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.

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.

4.9 out of 5 average rating, 42 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.

Guest suite in Faulconbridge

The exterior of Studio 1888 is framed by lush greenery and features a charming stone chimney. A well-maintained garden displays clusters of purple flowers, while a lamppost adds a decorative element, inviting guests to explore the peaceful surroundings.

4.9 out of 5 average rating, 394 reviews

Coomassie Studio: the charm of a historic property

This accommodation is ideal for those who prefer the rustic charm of a historic property over modern comforts. Warm and cosy in winter, the studio was once a purpose-built kitchen of a house built in 1888. Separate entrance. Recycled furniture, large bed, sofa, original fireplace and bathroom with shower cabin. Tiny veranda and a kitchenette, shared patio. NO KITCHEN. To use the fireplace, please BYO timber. For groups of 4 PLEASE CHECK OUR TINY COTTAGE next door.

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.

4.95 out of 5 average rating, 21 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.

4.98 out of 5 average rating, 103 reviews

The bedroom features a spacious bed with crisp white linens and a green throw blanket draped across the top. Flanking the bed are two bedside tables with lamps. Above the bed, three framed botanical prints are displayed on the wall.

Apartment in Rouse Hill

Sylish one bedroom unit overlooking piazza

Modern and stylish one-bedroom apartment @Rouse Hill Town Centre, just steps from the metro which will take you directly to Sydney’s CBD in about 40min. Featuring an open-concept layout, sleek finishes, and natural light throughout, this urban retreat offers both comfort and convenience. Perfectly located with cafés, shops, library and cinemas at your doorstep. Also enjoy the use of a pool, gym and tennis courts a short stroll away.

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.

4.97 out of 5 average rating, 29 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.

An expansive aerial view captures the serene Hawkesbury River flowing gently through the landscape, with the historic township of Windsor in the foreground. The sky transitions from soft pastels to deeper hues as the sun sets, highlighting the lush greenery and open fields surrounding the river.

4.85 out of 5 average rating, 62 reviews

River views near Blue Mountains

Beautiful 3 bedroom home with uninterrupted views of the Hawkesbury River. Walking distance to shops , hotels and located in the historic township of Windsor. This place less than an hour from Sydney is the ideal getaway for those looking to explore the magnificent historic Hawkesbury communities and some of the best bushwalks of the lower Blue Mountains. The area has excellent cycling and some fine restaurants and cafes.