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, 144 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, 125 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 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, 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.

Top guest favorite

An archway surrounded by lush greenery leads to a pathway into the guest cottage. Potted plants add a touch of nature along the path. A small dog is seen at the entrance, blending into the serene atmosphere.

Cottage in Kurrajong Heights

4.99 out of 5 average rating, 346 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 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

4.81 out of 5 average rating, 524 reviews

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!

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, 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.

Guest favorite

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

4.9 out of 5 average rating, 41 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

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, 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.

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

4.95 out of 5 average rating, 19 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.

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

4.98 out of 5 average rating, 162 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.

Guest favorite

A kitchenette area is presented, featuring a compact refrigerator, microwave, and electric kettle, all set against a vibrant sunflower mural. Storage cabinets are positioned beneath the countertop, creating an organized space for meal preparation and storage.

Guesthouse in Freemans Reach

4.93 out of 5 average rating, 56 reviews

The Reach Retreat - peaceful and comfy

Situated on a half acre property with lovely country views, you'll have peace and privacy in this recently renovated studio. The room features a queen 4 poster bed and a double sofa bed to accommodate up to 4 adults comfortably. Enjoy your stay in style, cleanliness and comfort and enjoy the use of the pool at your convenience. Please note the guesthouse is on a property shared with the main house which includes shared use of pool.

Top guest favorite

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

4.98 out of 5 average rating, 103 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.