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, 142 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, 120 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 wooden dining table is set within a cozy dining area, surrounded by leather chairs. A large mirror reflects the colorful mural on the wall. Glassware sits elegantly on the table, while a guitar rests nearby, adding a touch of warmth to the space.

Cottage in Kurrajong Heights

4.99 out of 5 average rating, 338 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 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, 162 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

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, 125 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 spacious patio area is enclosed by a wire fence, featuring a simple bench and table arrangement. The exterior of the cabin is clad in light-colored materials with several windows. A small stack of firewood is stored nearby, surrounded by lush greenery.

Cabin in New South Wales

4.93 out of 5 average rating, 260 reviews

Hawkesbury Haven - A rural retreat

Hawkesbury Haven Cottage is an as new, beautifully furnished, free standing cabin on 12 acres in a semi-rural area between Windsor and Richmond. It has a luxurious ambiance and so suitable for a romantic weekend or catch up with close family and friends. Full kitchen, gas and wood fire heating, air con, ceiling fans, fenced patio. Fresh farm eggs, bacon, tomatoes and bread provided for a full breakfast. Along with coffee and teas and cereal. With lots of friendly farm animals.

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, 435 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 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, 108 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.

Guest favorite

The living area features a cozy arrangement with a soft white sofa draped in a textured throw. A warm wood burner is positioned nearby, and a stylish coffee table is surrounded by leather poufs. Natural light streams through large windows, highlighting the inviting space.

Cottage in Grose Vale

4.87 out of 5 average rating, 180 reviews

Kurrajong tranquil cottage on acres pet friendly

Sparrow Hall is a stunning farm cottage with log fire 3 bedrooms on our 14 acres in the beautiful Hawkesbury area, 1 hour from Sydney. . Enjoy valley views, a private fenced garden and paddock for the kids to run free. Listen to the bellbirds and feed the horses and goats. Enjoy the outdoor fire pit and stars at night. Explore the lookout in the Blue Mountains, walking tracks and riverside beaches just minutes away.

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

4.8 out of 5 average rating, 102 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.

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, 502 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.