Holiday houses in Winston Hills

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Top-rated holiday rentals in Winston Hills

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Guest favourite
A clear view of a solar-heated pool reflects the sunlight, accompanied by a shade umbrella. A jacuzzi spa is positioned nearby, with seating arranged around a small table. Lush greenery surrounds the area, creating a private and tranquil outdoor space.
Guest suite in Wahroonga
4.91 out of 5 average rating, 427 reviews

Resort style self-contained unit. Pets welcome.

Resort style living. Self contained apartment on the Nth Shore of Sydney. Set in trees in quiet & exclusive suburb of Wahroonga. Pets are welcome & can sleep inside. Secure private back yard. Close to start of M1 - Nth or Sth. Walk to SAN. 10 min walk to train & village - ex restaurants & coffee shops. 35 min to city. Apartment is the lower floor of an executive home (totally private). Solar heated pool, Jacuzzi Spa, Pool Room & Summer House. Pillow top bed is super comfortable plus Sofa bed AC.

Top Guest favourite
A private balcony offers outdoor dining with a table set for two, accompanied by vibrant views of the water and distant city skyline. Lush greenery frames the scene, while tranquil blue waters reflect the clear sky.
Condo in Mosman
4.98 out of 5 average rating, 190 reviews

Absolute Harbourfront Apartment with Fabulous Panoramic Views

Magnificent piece of paradise at the waters' edge. Heart stopping views from every room (Guest 2017) Bright & sunny, idyllic waterfront sanctuary Separate home office All linens and unit professionally cleaned Alfresco balcony perfect for drinks/meals BBQ dining, sun lounges, harbour pool Onsite parking: max. car height 1.7 metres Bus & ferry close Fireworks often seen, spectacular on New Year's Eve & Australia Day Peaceful by day, stunning by night Come and chill out – you won't want to leave!

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.

Guest favourite
A cozy seating area features two plush armchairs positioned near a large window, providing unobstructed views of the ocean and cliffs. A small side table holds two glasses of wine, and a potted plant adds a touch of greenery.
Apartment in Vaucluse
4.96 out of 5 average rating, 110 reviews

Stunning 1bdr w/ Amazing View

Bright and airy one bedroom apartment nestled on top of Diamond Bay Cliffs with breathtaking ocean views. The stunning view overlooking the cliffs and the soothing sound of waves, provide an incredible connection to the ocean from awe inspiring sunrises to frolicking whales throughout the day. Relax with a wine or coffee in this beautifully styled home surrounded in comfort and serenity. Take a dip in the pool overlooking the ocean or take a walk along the cliff walkway. Free street parking

Top Guest favourite
A modern dining area is set for six, featuring a sleek black table with matching chairs. Soft lighting highlights the elegant decor. Floor-to-ceiling windows offer expansive views of the city skyline, while a cozy lounge area with armchairs and a side table complements the space.
Apartment in Westmead
5 out of 5 average rating, 109 reviews

Westmead Public Hospital, WSU, train within 400m

Enjoy a stylish experience at this centrally located 2-bedroom apartment Plus: car space x 1, spectacular night views to Parramatta, furnished like a home away from home At your doorstep: - Westmead Hospital (300m) - WSU (220m) with a food / retail shops, including GYG, Japanese, Vietnamese, cafe, barber, nail salon, Chatime - Train Station (400m); 4 stops to the city; direct line to Blue Mountains - Light Rail (300m) NOTE: Ideal for 4 guests; 1 camping bed (max weight 130kg) on request.

Superhost
A modern kitchen area features a dark stone countertop, with a kettle and decorative plant positioned near a large glass window. Beyond the window, a private pool is visible, surrounded by wooden decking and tropical trees, creating a serene outdoor space.
Tiny home in Seaforth
4.89 out of 5 average rating, 269 reviews

Spa Serenity Cottage with Private Pool & Spa

This is a Granny Flat located at the back of our property, with its own private entrance and complete privacy. The pool, spa, and backyard are exclusively yours, no one else shares these spaces. Just so you’re aware, we live in the main house at the front. While you may occasionally hear us, we’re very quiet and respectful of your space. Please respect the neighbourhood while you are listening to your music and keep the noise down. Your retreat is fully private, we absolutely respect that.

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, 169 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, 123 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

Guest favourite
A bright living area is showcased with large bay windows offering sweeping views of the ocean. A light-colored sofa and decorative cushions are arranged invitingly. Natural light floods the space, highlighting the wooden flooring and a modern television unit. The open door leads to a balcony.
Holiday home in Manly
4.93 out of 5 average rating, 127 reviews

Panoramic Views & Beach Front Fairy Bower

This top floor apartment undoubtably has one of the best views and locations in all of Manly. Featuring eye watering panoramic views over Manly beach as well as Fairy Bower and Shelly beach. Fairy Bower is the perfect swimming spot due to its protected location and ocean pool, which makes it perfect for families. The bay window is perfect for gazing down to the promenade, reminiscent of the Italian coastline with bathers sprawled over the rocks soaking up the summer sun.

Guest favourite
Bright living room features a large bay window that offers expansive ocean views. A comfortable gray sofa is surrounded by decorative pillows and a textured throw. A round coffee table sits in the center, complemented by a flat-screen TV on a wooden console.
Apartment in Manly
4.94 out of 5 average rating, 128 reviews

Unique WATERFRONT Apartment

Situated between Manly South Steyne and Shelly Beach lies the romantic sounding Fairy Bower. Designed for the quintessential Northern Beaches lifestyle, this top-floor unique Manly apartment is an entertainers delight offering a 180-degree ocean view. Take a surf check from the shared rooftop balcony, or just enjoy the iconic breaks of Manly Beach. With this million-dollar view, you won’t even need to leave this coastal sanctuary to feel like you’re at the water’s edge.

Superhost
A spacious bedroom features a queen size bed with neatly arranged towels. A sofa lounge and dining table are included, while large glass doors allow natural light and provide access to an outdoor seating area. A wall-mounted TV is positioned for easy viewing.
Guest suite in Castle Hill
4.79 out of 5 average rating, 170 reviews

Geraniums—self contained unit with flair

Geraniums is fully self-contained, nestled within a building among other individual units. The main entrance is accessed by all guests; each unit is secured with its own smart lock. Geraniums was recently refurbished with a modern kitchenette and bathroom. The suite also features architecturally designed skylight ceilings and French doors opening onto a courtyard. It is within walking distance to public transport, Castle Towers and Piazza. Parking is onsite.

Popular amenities for Winston Hills holiday rentals