Holiday rentals in Windsor Downs

Regentville Waterfront-Millionaire Lifestyle Lux

Live the millionaire lifestyle in this Miami-style resort home on the Nepean River Waterfront, 6 bedrooms for 8 guests, Hamptons Styling, Designer Kitchen, seamless flow to entertaining Balcony, Breathtaking River views run through both levels of the house. There's a resort pool that's rare in this pocket of Penrith, a hot tub that runs year-round & a kitchen built for a proper Sunday roast. BBQ, 5 G Wifi, You're 3 minutes from Penrith's cafés, with the Blue Mountains at the end of the street.

Location · Family · Checkout

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

Family · Value · Comfort

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.

Location · Family · Grill

Spacious 5BR Home | Free Parking | 9 min to HomeCo

✨Peaceful Stays, Starry Nights✨ Planning a short getaway?Escape to our serene retreat with parking in Marsden Park.Start your day cuddling a koala at Featherdale Wildlife Park,just a short drive. Shop & grab tasty bites at Rouse Hill Town Centre, only 10 mins by car. Spend a lazy afternoon picnicking & soaking in the sunset at Western Sydney Parklands, just 20 mins away. Unwind in our spacious backyard & gaze at the starry sky with your loved one Perfect for families seeking a peaceful retreat

Location · Value · Parking

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.

Family · Location · Indoor spaces

Luxury Dream Holiday Relax(House)

Spacious Family Retreat – 4BR, Stylish Comfort, Close to Shops & Nature This modern and spacious two-level home in Marsden Park offers comfort, convenience, and style – ideal for families, groups, or business travellers. With 4 cozy bedrooms and 2 bathrooms, there’s plenty of space for everyone to relax and enjoy. The home is located in a peaceful neighbourhood, just 45 minutes' drive to the stunning Blue Mountains National Park, making it a great base for day trips and outdoor adventures.

Location · Family · Cleanliness

Brand-New and Private Granny Flat in Quakers Hill

Brand new 2 bedroom 2 bathroom Granny flat in Quakers Hill NSW, Conveniently located close to Kellyville Metro and Stanhope Village This granny flat can host maximum 4 guests and features: 1 master bedroom with en-suite bathroom -1 bedroom with one double bed -1 bathroom with wash machine and dryer combo -1 living room with smart TV - Free wifi available -1 spilt aircon system with cooling and heating function, Plenty street parking, - Very quiet place for relaxing - 40 mins to Sydney CBD

Family · Value · Amenities

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.

Value · Location · Laundry

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.

Family · Location · Accuracy

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

Location · Family · Hot tub

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.

Family · Location · Layout

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.

Location · Family · Nearby