Holiday rentals in South Windsor

Greenview Guesthouse

A luxury rural retreat on 30 acres close to the village of Richmond. Tucked along the scenic Hawkesbury River, this private, beautifully appointed guesthouse offers a peaceful retreat while close to the conveniences of Richmond. Just two minutes from town, guests can enjoy great coffee, boutiques, farmers market and the charm of this historic area. For those seeking adventure, the Blue Mountains are a 10-minute drive away, offering hiking and biking trails, charming cafes, and spectacular views.

Scenic Barn-Panoramic Sunroom w Fireplace Pool Tbl

Escape to this refined & luxury barn set on a private rural property on half hour drive to Blue Mountains. Offering plenty of space to enjoy the magnificent & picturesque views, shoot some pool or binge-watch movies on large smart TV with stunning acoustics while relaxing on "lay-z-boy" recliners. Perfect for family or a small group of friends. The Barn features panoramic views of Hawkesbury valley, it is thoughtfully designed with quality furnishings. It is ideal for relaxing & entertaining.

Luxury 4BR Retreat | Private Pool & Spa

A private luxury retreat designed for couples, executive stays, and discreet business meetings. This elegant 4-bedroom home features a private pool and spa bath (jets, not heated), refined designer interiors, and spacious living areas. Created by a professional chef and hospitality entrepreneur with 15+ years of experience, it offers premium bedding, fast Wi-Fi, Netflix, a fully equipped kitchen, and easy self-check-in. A calm, five-star alternative to a hotel, private, polished, and peaceful.

Luxury Architect-Designed Escape with Pool & Sauna

Architect-designed luxury escape nestled in the foothills of Blue Mountains, just 1 hour 15 minutes from Sydney CBD. This award-winning retreat blends modern design with nature, featuring a stunning pool, sauna, double sided-fireplace, expansive decks with sydney views. Three spacious bedrooms spread across pavilions, it’s ideal for romantic getaways, small group stays, or your own private wellness retreat. Nestled in the Hawkesbury hinterland - perfect to unwind and reconnect all year round.

Quiet country getaway in stylish 2 bdrm shed

There's nothing like a fire in winter! The Shed is a cosy retreat in the Hawkesbury Valley, 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.

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

The Chateau

This beautiful newly renovated two bedroom Cottage is known for its luxury Chateau feel.. it is the most peaceful place to enjoy the sunsets and stars. Here you will rest in the landscape of the sky. Get away from the hustle and enjoy this acre of love. The Cottage is perfect for a low key weekend getaway whether it's with your partner or friends. Perfect for newly weds, or for some soul searching. So many adventures in the hawkesbury to enjoy, We can't wait to host your luxury stay x

Tiny Home - Nestled in Nature

Step into our cosy tiny house in the Hawkesbury, set on 27 lush acres, the perfect place to slow down and switch off. Located just 10mins from historical Windsor. Sleep beneath the stars in a queen loft, soak in the outdoor bath, or gather by the fire pit. Enjoy meals on the covered deck or unwind in the games and movie loft with projector, Nintendo Switch, board games, puzzles and books. Popcorn included. Follow @fernhaus_airbnb on Insta. Not suitable for children under 12.

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 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.

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.

6sixteen The Banks

Welcome to 6SIXTEEN The Banks your peaceful country escape in Richmond, NSW. Set on 5 acres with sweeping views toward the Blue Mountains, this tiny retreat is perfect for couples, solo guests or small families wanting to unwind. Soak under the stars in the wood-fired hot tub, refresh with a cold plunge, or melt into a private infrared sauna session (optional wellness upgrades available). Hosts nearby if needed. Sauna launching Mid March

Farm resort with a view to relax

Reconnect with nature at this unforgettable escape. On a picturesque farm, on door step to Scheyville National Park, only minutes' drive to town centre. Spanning across a spectacular 6 acres, this picturesque getaway is the perfect fusion of dreamy country living with contemporary interiors and pure relaxation. With amazing views of the tranquil countryside, and an amazing pool to occupy any downtime we know you'll be happy.