Vacation rentals in South Windsor

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Top-rated vacation rentals in South Windsor

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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, 146 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
Guesthouse in Ebenezer
4.98 out of 5 average rating, 128 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.

Guest favorite
The kitchen features a spacious wooden countertop with a black sink and modern appliances, including a kettle and microwave. Shelves hold glassware and jars, while framed botanical prints add a decorative touch. Warm lighting is provided by wall sconces above the countertop.
Guesthouse in Richmond Lowlands
4.82 out of 5 average rating, 152 reviews

Pretty Country Accommodation on Prestige Property

Set on the banks of the Hawkesbury river on 30 acres, this beautiful apartment is a delightful escape. Conveniently located two minutes from historic Richmond where guests can enjoy coffee & speciality shopping. The accomodation has been built specifically for Airbnb guests. It is has all the modern comforts & is cleaned professionally. Lots secure parking Other properties on site Modern Accommodation - 3 bedroom 1 bath Cute Accomodation - 2 bedroom 1 bath HORSES ACCOMODATION ENQUIRE

Top guest favorite
A view through large glass doors reveals a spacious green yard with grazing horses. Tall trees provide shade, while a fenced area can be seen in the background. Soft curtains frame the scene, allowing natural light to brighten the interior space.
Farm stay in Kurrajong
4.99 out of 5 average rating, 175 reviews

Country cottage with beautiful farm and garden

Private, 2 bedroom country cottage with uninterrupted views of lush pasture and mountain ranges.. just 1 hr from Sydney. Keep snug and warm with internal wood fire plus chiminea on deck. Horses, chooks, cows, wild deer & ducks. Explore 12 acres of paddocks, with dam and creek, or stroll our formal gardens with many private vistas to sit and relax. Close to Kurrajong Village. Short drive to Bilpin orchards & Mt Tomah Botanic Gardens. Easy day trip to the Blue Mountains & ZigZag Railway.

Top guest favorite
Tiny home in Yellow Rock
4.97 out of 5 average rating, 135 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

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
4.93 out of 5 average rating, 443 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
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
4.89 out of 5 average rating, 406 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
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, 166 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 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, 105 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 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
4.97 out of 5 average rating, 31 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.

Top guest favorite
A warm living area features wooden beams and blue walls that complement a brown leather sofa. Two wooden ladders lead to loft sleeping areas, while framed artwork and mirrors add character. A cabinet and lamp provide functional accents against the inviting backdrop.
Guesthouse in Windsor
4.92 out of 5 average rating, 515 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.

Top guest favorite
Vacation home in Wilberforce
4.93 out of 5 average rating, 106 reviews

Silver Saddle Three Bedroom Cottage with Pool

This rustic and luxurious three-bedroom cottage is located just 15 minutes out of the town of Windsor in Sydney's west. Enjoy the serenity of open-air and peaceful landscapes as you indulge in a comfortable getaway with nature right on your doorstep. A outdoor patio overlooks a crystal clear pool, giving you a holiday experience that doesn't compromise. IG: @silversaddlecottages

Popular amenities for South Windsor vacation rentals