Book a Holiday in Sydney

Photo Credits: Made Comfy

Need a break? Book a holiday in Sydney! Wait no more. The Smiling Stays is here. Now open for bookings! 👏 🥂

Tucked away on the tranquil, tree-lined Hopewell Street in the heart of Paddington, Sydney, The Smiling Stays is more than just a cozy accommodation – it’s a soulful space for both wandering hearts and working minds. Whether you’re visiting Sydney for the first time or simply seeking a fresh perspective close to home, this is your sanctuary.

Why Paddington? Because it’s a place where stories live in the walls. Just a heartbeat from the Sydney CBD, Paddington is a neighbourhood drenched in heritage and alive with modern flair. Think lacework Victorian terraces, golden sandstone buildings, and charming corners that make you slow down and smile. As you wander these leafy streets, you’ll find independent boutiques, art galleries, and quaint cafes humming with creative energy.

Start your day with a book and a brew at Ampersand Café & Bookstore, or sip a perfect espresso at Paddington Alimentari, surrounded by European provisions and locals chatting in the sunshine. Stroll through the Five Ways intersection, where fashion, food, and friendly faces converge in one of Sydney’s most beloved pockets.

Art lovers will be spoiled for choice with over 15 galleries to explore – from the experimental works at Saint Cloche to thought-provoking installations at the Sherman Contemporary Art Foundation. And just across the way, you’ll discover a true hidden gem: the Paddington Reservoir Gardens, a sunken oasis blending ancient stonework with tranquil reflections, where history meets serenity.

On Saturdays, the iconic Paddington Markets bring the suburb to life. Here, stallholders offer up handmade crafts, designer pieces, and gourmet nibbles in the shade of the Uniting Church – it’s the kind of place where you find something you didn’t know you were looking for.

And when the sun dips below the rooftops, culture lingers. Catch an indie film at the heritage Chauvel Cinema, or step inside the majestic Paddington Town Hall, where ideas and community collide.

And through it all, there’s The Smiling Stays. A place to pause, to create, to recharge. To feel at home while being gently nudged out of your routine. It’s a passion project born from love, laughter, and the spirit of discovery.

Please help us to spread the word. Now open for bookings. 🥑👇


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