Holiday houses in South Windsor

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Top-rated holiday rentals in South Windsor

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Top Guest favourite
Cottage in Riverstone
4.96 out of 5 average rating, 74 reviews

The Bakery

Take it easy at this unique and tranquil getaway. The Bakery is self contained. You can have a relaxing soak in a free standing bath, lay under the Callistemon tree in a hammock or enjoy sitting by a cozy wood fire in winter. Located just a short walk (7 min) to the rail and bus and within easy reach to many scenic locations in the Hawkesbury region or the Blue Mountains. Check out my guide books. People with mobility issues may need to check if they can access the bath or lounge as it is low

Top Guest favourite
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, 137 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 favourite
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, 148 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
Guest suite in Freemans Reach
4.99 out of 5 average rating, 104 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.

Guest favourite
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.
Guest suite in Faulconbridge
4.9 out of 5 average rating, 439 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.

Guest favourite
Home in Windsor
4.93 out of 5 average rating, 27 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 favourite
Tiny home in Freemans Reach
4.97 out of 5 average rating, 35 reviews

The Bunker

Step inside this beautifully designed 170-sq-ft tiny home that proves small can be spectacular. Surrounded by open space with panoramic views, it features a queen bed for dreamy nights, split air-conditioning, and a fully equipped kitchen with everything you need. The modern bathroom offers a gas-heated shower, flush toilet, and stylish basin, because tiny living should never mean compromising on comfort. Perfect for a retreat, recharge, or couple’s escape.

Top Guest favourite
Apartment in Rouse Hill
4.98 out of 5 average rating, 113 reviews

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.

Top Guest favourite
Home in Windsor
4.97 out of 5 average rating, 34 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.

Guest favourite
Home in Windsor
4.86 out of 5 average rating, 66 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.

Top Guest favourite
The exterior of the barn reveals rustic wooden siding accompanied by a deep red door. Natural landscaping surrounds the structure, including trees and vibrant greenery, creating a charming and inviting outdoor area.
Guesthouse in Windsor
4.92 out of 5 average rating, 526 reviews

1830's converted barn with sauna

This barn dates back to 1830's but it has been fully renovated to a studio apartment with all modern comforts. It is one open space with living area and two sleeping lofts, one with queen bed, the other with 2 single beds. A bit like a giant cubby house! The shops are just 5 minute stroll away, and so is the river and train station. You share a garden with a spa and BBQ with the main house where we live.

Guest favourite
A spacious bed is centered against a neutral wall, adorned with a colorful geometric-patterned duvet cover. Flanking the bed are two wooden nightstands, each featuring a lamp and a vase filled with flowers, adding a touch of warmth to the room.
Guesthouse in Jordan Springs
4.82 out of 5 average rating, 279 reviews

Seperate studio with private entrance in Penrith

We would like to offer our newly renovated separate lockable unit with semi kitchen (with induction cooktop) and bathroom in Jordan Springs, Penrith. Unit is situated at the back of the property and has seperate entrance from right side of the property. It has split air con and all necessary cooking amenities required for comfortable long or short term stays.

Popular amenities for South Windsor holiday rentals