The Best Luxury Winter Getaways from Sydney

When winter sets in, the city can often be the last place you want to be. Thankfully, out in country New South Wales a host of warm treats await. From mulled wine to open log fires, these destinations both embrace and harbour you from the cold weather. Outside the peak travel season, winter getaways are usually limited to just a long weekend. This means you need a destination that is guaranteed to deliver without too much time in transit. Enter, the road trip. After exploring country towns up and down the state, I’ve found a few favourites that I keep returning to. They’re the kind of towns that make for immersive winter getaways, with sights, sounds and smells to melt away the cold. And as you’ll see below, they don’t skimp on modern comforts. Here are the places offering up the most luxurious winter stays outside of Sydney…




Tucked between the hills of the Shoalhaven region, Kangaroo Valley offers up quaint country living just 2 hours south of Sydney. Surrounded by bushland that hugs the Kangaroo River, this tranquil setting is perfect for switching off from the rest of the world. Culinary treats include; homemade pies from the Barrengarry Old Store, old-fashioned fudge, Kangaroo Valley olives and wine from nearby Yarrawa EstateThe General Cafe also serves up fresh sourdough, organic coffee and scrumptious meals with a focus on fresh local produce.

When driving to Kangaroo Valley from Sydney don’t miss the opportunity to stop by Fitzroy Falls.  The walking trails and lookouts are a good opportunity to stretch your legs and take in the spectacular view.


As far as country cottages go they don’t get much better than this eclectic and beautifully-styled gem in Kangaroo Valley. Curated by stylist Lisa Madigan, The Cottage is a reflection of her environmental influences and artistic endeavours. Luxurious linens, a deep plunge bath and lush breakfast hamper bring modern comforts to a rustic setting. A generous space for couples, this setting is perfect for hunkering down by the fireplace or enjoying local produce at the harvest table.

The Cottage Kangaroo Valley accommodation.The Cottage Kangaroo Valley winter getawaysThe Cottage Kangaroo Valley winter getawaysThe Cottage Kangaroo Valley accommodation

Photography by Lean Timms of Lean and Meadow.


Escaping winter doesn’t mean that you have to miss out the natural wonders that it brings. Snow lovers will want to hit the slopes just as much as retreating to the warmth afterwards. Thredbo offers both of these experiences with its alpine village and cabin-style accommodation. The village itself is home to bars, cafes and restaurants so you don’t have to venture far for hearty meals. The slopes offer some of the longest runs in Australia, dotted with bars for the perfect après-ski.


Just a 5 minute walk from the village center, The Eastern is an architectural haven suited to couples seeking out great design. With breathtaking views out to High Noon ski run, the studio provides a sense of seclusion amongst Mount Kosciuszko. Heated floors and a ski storage room make this chic space practical and comfortable. I love the minimalist design of The Eastern and how it doesn’t detract from its natural surrounds.

The Eastern Thredbo winter getawaysThe Eastern Thredbo winter getawaysThe Eastern Thredbo winter getawaysThe Eastern Thredbo winter getaways

Photos from The Eastern Thredbo Village.


When I think of the Blue Mountains I am instantly reminded of smoky, crackling log fires and fog stretching over the valley below. A drive through the region will bring you to Leura, Katoomba, Blackheath and Lithgow. Each charming country town boasting bakeries, quaint cottages and antique stores to get lost in. The Three Sisters at Katoomba will satisfy nature lovers, with its rock formations standing proudly against a misty blue. On your way there, Leura mall is the perfect stop for picking up provincial-style homewares and souvenirs. By night, Silk’s Brasserie provides a cosy, romantic setting to enjoy a farm-focused menu. If you love rummaging through antiques like I do, you must stop at Victory Theatre Antique Centre in Blackheath. This original Art Deco facade holds two storeys of antiques, jewellery and art…with plenty of cafes nearby for a pit stop.

Driving further towards Lithgow and over the Blue Mountains, the landscape changes once more. Valleys extend into lush meadows that lead your eyes to the next town. The old Lithgow Brickworks and Zig-Zag Railway gives an insight into the regions history. This is also the gateway to Bells Line of Road, a great scenic route to take on the way home.


Emirates One&Only Wolgan Valley is the epitome of luxurious and tranquil accommodation in the Blue Mountains. This conservation-based resort celebrates its natural surrounds through cuisine, activities and holistic spa therapies. One&Only’s free-standing villas boast high ceilings and expansive windows, opening up to the breathtaking valley. My favourite feature would have to be the enclosed private pools offering a warm dip under the stars.

One and Only Wolgan Valley Blue Mountains AccommodationOne and Only Wolgan Valley RestaurantOne and Only Wolgan Valley PoolOne and Only Wolgan Valley Wollemi Villa

Photos from One&Only Wolgan Valley.


Bowral is my favourite town in the Southern Highlands. I find it has a great mix of country charm, modern retail and farm fresh cuisine. Acting as the hub of the Southern Highlands it is a great place to explore the surrounding farms and villages from. Only an hour and a half from Sydney, Bowral is also the easiest of these locations to retreat to for shorter breaks. I have stayed at Milton Park Country House which is surrounded by beautiful sculpted gardens and styled in French provincial decor. I also shot a winter editorial at Fitzroy Inn in nearby Mittagong. It is a smaller, restored property with beautiful common areas and open log fires.

In Bowral itself you can’t go past The Press Shop for a beautiful cafe setting with a side of stationery. This cafe is an interior lover’s dream with plates as pretty as their prints. When it comes to dinner, Biota offers up tasting menus showcasing local produce, matched with Australian wines. This one is a must for food connoisseurs with plated meals resembling works of art.


Now I know that this place is a little roomy for couples but I couldn’t write a winter getaways guide without including it. The Rift Estate in Bowral is home to a huge Victorian Italianate mansion and original stables. The latter becoming a 6-bedroom residence called the Coach House. More suitable for a bridal party or family getaway, it’s the perfect excuse to round up your friends and book the whole house! The interior has been restored in keeping with 19th century style and sits amongst cold climate gardens in the broader estate.

The Rift Bowral winter getawaysThe Rift Bowral winter getawaysThe Rift Bowral winter getawaysThe Rift Bowral winter getaways

Photos from The Rift Bowral.


Okay, so for this one you will need a plane ticket. I just can’t resist a bit of north coast sunshine during winter. However, Byron Bay’s weather is not the only thing luring visitors there for winter getaways. Its beautiful beaches, relaxed lifestyle and foodie hot spots provide the perfect destination for a wholesome trip. Get your retail fix from Hope & May where you can stock up on beach essentials and coastal pieces to take back home. As I mentioned, there is no shortage of great places to eat. One place I wouldn’t miss is Three Blue Ducks at The Farm, serving up produce grown on their farm and providing picnic hampers to enjoy in the surrounding fields. For sunset drinks head to Balcony Bar where you can swap the frozé for mulled wine in winter.


The thing I love most about accommodation in Byron is the old queenslander houses that have been converted into guest rooms. One conversion in this style is 28 Degrees. The stunning, weatherboard, 2-storey space has been fitted out with luxe linen and bohemian decor. The use of raw textures throughout gives the guest house an authentic beachside feel without compromising on modern comforts. With an outdoor shower and private plunge pool, this space is made for embracing the winter sun.

28 Degrees Byron Bay Emma Kate Co

Photography by Emma Kate Co.

28 Degrees Byron Bay outdoor shower28 Degrees Byron Bay linen

Image via Well Travelled Bride on Instagram.

28 Degrees Byron Bay Bathroom

Photo from 28 Degrees Byron Bay.


How do you like to escape during the colder months? Are you the kind of traveller to retreat to the sun or slosh about in the snow? I like both kinds of winter getaways but tend to opt for country warmth when my time is limited. As you can see, there is no shortage of stunning properties to indulge in. I really love the emergence of boutique accommodation that is authentic in its design. These spaces transport you to the very essence of each town which is exactly what you want from a seasonal escape. If there’s another winter destination you like to retreat too please mention it below. I am always building my bucket list!

Happy travels,

Jess sign off

Header Image Photography by Lean Timms.

Jessica Rule

Jessica Rule

Jess is a travel photographer who draws on her background in styling to curate the most stylish escapes. She works alongside her husband Justin to produce travel videos for brands and destinations.