Holiday houses in Winston Hills

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Top-rated holiday rentals in Winston Hills

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Guest favourite
The living area is characterized by large glass doors opening to a scenic view, allowing natural light to fill the space. A comfortable seating arrangement is present, with a soft blanket draped over a couch. A dining table and rustic shelves are located in the foreground.
Guest suite in Cowan
4.98 out of 5 average rating, 183 reviews

The Lotus Pod - Unique Guesthouse with views

Situated in the grounds of Austral Watergardens nursery, this large,spacious studio is located approx. 50 mins drive north of Sydney. On the doorstep of the Hawkesbury River and Berowra Waters, the Lotus Pod offers a country escape or romantic getaway. With magnificent views across the pristine Mougamarra Nature Reserve and surrounding gardens, a perfect place to relax & unwind. Visit the local eateries, enjoy fresh seafood on the River, Ferry Rides, The Great North walk & bushland scenery

Top Guest favourite
A cozy tiny house is set against a natural backdrop, featuring wooden accents and a gravel path. Outdoor seating is positioned to offer scenic views, while the surrounding vegetation enhances the tranquil atmosphere. The structure is designed to blend harmoniously with the landscape.
Tiny home in Razorback
4.99 out of 5 average rating, 275 reviews

Razor Ridge Retreat-Tiny House- Pet Friendly-Views

PET FRIENDLY!!! "RAZOR RIDGE RETREAT" / "A LITTLE SLICE OF AUSTRIA" is the first of its kind in the Razorback area. It's a cosy, luxury "Tiny House" located in an idyllic bush setting on a 5 acre property in the Razorback ranges, about an hour's drive from Sydney. The tiny house is nestled safely on the edge of a ridge where day & night, spectacular uninterrupted views to the Sydney skyline can be enjoyed by you with magical sunrises and sunsets seen from your bed and also the wild birdlife.

Top Guest favourite
A spacious lounge and dining area is highlighted by a round wooden table with four chairs. A comfortable sofa is present alongside large windows that offer natural light, framed by soft curtains. The kitchenette is equipped with modern appliances including a microwave and fridge.
Guest suite in Beecroft
4.98 out of 5 average rating, 180 reviews

Apartment in quiet leafy suburb

New, private, self-contained flat with off street parking & separate entrance. Continental breakfast & snacks included. Close to main transport routes such as Beecroft train station (40mins to City), buses to City, M2, NorthConnex & M7. Good shopping nearby (Castle Hill, Macquarie, Parramatta etc). Cumberland State Forest, Koala Park & Golf Club within 5mins & Olympic Park (Accor Stadium & Qudos Arena) approx 30 mins drive or bus. Free EV charging included; bring your own cable (240VAC, 2.4kW).

Top Guest favourite
A spacious bedroom is equipped with a large bed, complemented by a neutral blanket and decorative pillows. Natural light filters through the glass sliding doors, offering views of the surrounding trees. Side tables with lamps provide soft lighting, enhancing the serene ambiance.
Guesthouse in Glenhaven
4.96 out of 5 average rating, 140 reviews

Five Bees Bush Retreat Guest House

This luxurious guest house is nestled amongst trees with a stunning view over the surrounding bush valley. Situated in the leafy and hilly suburb of Glenhaven, you feel like you're in the middle of the Australian bush, yet are still close to shops, restaurants, train station and other amenities. There is a private deck off the bedroom where you can enjoy breakfasts or sundowners (weather permitting). The property is situated apart from the main residence and has a separate and private entrance.

Guest favourite
The exterior of the house is viewed from the street, showcasing a brick façade and a well-maintained front garden. A winding driveway leads to the entrance, flanked by greenery. A tranquil atmosphere is noted with clear skies and palm trees in the backdrop.
Guest suite in Baulkham Hills
4.87 out of 5 average rating, 116 reviews

Quiet and spacious self-contained unit

The unit is on a quiet cul-de-sac street close to a large reserve. It has its own amenities and entrance that you don't share with anyone else. Bus stop to Parramatta or Castle Towers is 300 metres away. 800 metres to the bus stop on M2 and you can be in the city after 3 stops. 5 minute drive to 2 Shopping Malls. The unit is on the left end of the whole house. Its bedroom and bathroom are upstairs;the kitchen/dinning and washing machine are downstairs. NETFLIX and NBN WI-FI are provided.

Top Guest favourite
A wooden boathouse floats on calm waters, surrounded by sailboats and lush hills. The structure features a dark exterior with a single door and a large window. Soft clouds float in a blue sky, reflecting the tranquility of the setting.
Houseboat in Newport
4.99 out of 5 average rating, 261 reviews

The Salty Dog

As seen on Ch7 Morning Sunrise, House&Garden, Inside Out, Homes to Love Au, My Favourite Stays Au & NZ, Stayawhile magazines and Sommerhusmagasinet (Europe) The smell of salt air, the sound of water lapping, the sun glinting off ripples that surround you...a feeling of peace and the world left behind. The Salty Dog is a space that is both cosy and open to the water, a wooden boathouse for two that invites you to relax and just 'be', to go off grid and reconnect with mother nature at her best.

Top Guest favourite
A bright studio space features a king size bed with plush pillows, a cozy sofa, and a modern coffee table. Large windows allow natural light to fill the room, overlooking greenery. A smart TV is mounted on the wall, and a ceiling fan adds to the comfort.
Guest suite in West Pennant Hills
4.98 out of 5 average rating, 265 reviews

Sanctuary in West Pennant Hills.

Quiet and Private Purpose-built studio. Own entrance and Bathroom. Modern fittings with a king size bed plus an electric blanket in winter. Luxury linen and toiletries. Smart TV, Kitchenette with a stone bench. Aircon, Microwave, toaster, tea /coffee (instant and Nespresso)A light breakfast is provided. BBQ and private porch. Wardrobe. New washing machine. Wake up to the sound of birds. LGBTI friendly. Secure gated parking. Business travelers/regular guests qualify for a loyalty program.

Top Guest favourite
A covered outdoor area features two wicker chairs set on a wood deck, inviting relaxation. A view into the interior reveals a spacious dining table surrounded by modern chairs, illuminated by soft overhead lighting.
Guest suite in Wahroonga
4.98 out of 5 average rating, 174 reviews

Rainforest Tri-level Townhouse.

Enjoy a peaceful stay in this updated tri-level townhouse, among leafy, tree-lined streets. With its own separate access, off-street parking, and ample safe street parking available, this home offers privacy and convenience. Perfectly located just off the M1 motorway, it’s an ideal stopover along the M1, while also being close to the SAN Hospital, major schools and shopping. Nearby parks, an oval, and bush walks add to the tranquil setting, an ideal base for short or longer stays.

Guest favourite
A serene outdoor space features a sparkling pool surrounded by tiled flooring and a lush green plant. A shaded seating area with a straw umbrella is visible, adding comfort and relaxation to the setting. The backyard is enclosed by fencing for privacy.
Guesthouse in Northmead
4.89 out of 5 average rating, 125 reviews

Private Pool Villa

The Pool guest house is a unique 2 bedroom self contained & newly renovated space . Totally private !! You have your own private entry & parking is at the door. The guest house has 2 bedrooms , bathroom , shower & a separate toilet . It also has a lounge room with a 2.5 seater sofa's and a smart Tv . The outdoor patio area has a kitchenette , lounge seating , dining table , barbicue area , fireplace , sunlounges & an amazing pool . Highchair & Cot are also available for toddlers

Top Guest favourite
Guesthouse in St Ives
4.99 out of 5 average rating, 128 reviews

Luxury Garden Cottage Retreat - Romantic & Restful

Arriving through antique gates, wander down wisteria covered walkway to your home away from home. Outdoor tiled undercover area with dining/living space, lit in evenings with silk lanterns invite you outside for a special occasion. Light-filled cottage, open plan living/dining area. Bedroom boasts plush queen bed for a blissful nights' sleep. Bathroom invites indulgence with a rainforest shower. Fully equipped kitchen with washing machine. Thoughtful touches throughout.

Top Guest favourite
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
4.99 out of 5 average rating, 134 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.

Guest favourite
A modern kitchen features purple cabinetry and sleek countertops. Kitchen appliances include a gas stove, oven, and fridge. Two bar stools are positioned at a small island, with pendant lighting hanging above. A small decorative plant is placed on the counter for added charm.
Home in North Rocks
4.85 out of 5 average rating, 103 reviews

Quiet & Modern 3-Bedroom House

Bring the whole family to this delightful 3-bedroom home with beds for 5 guests. Hidden away from traffic but conveniently located near a new large Woolworths Supermarket. It’s a 5-10min drive away from multiple cafe’s, restaurant’s, shopping centre’s, as well as Westmead Hospital & Lake Parramatta. Please read the “Where you’ll be” section under the map for transport & distance information.

Popular amenities for Winston Hills holiday rentals