Vacation Home w Private Rooftop and Harbour View

Hotel Description

You know what caught me off guard about this place? The moment you step onto that rooftop, Sydney just unfolds in front of you in this way that makes you forget you’re staying in what’s essentially a vacation rental. I mean, 36A High Street puts you right in the thick of the CBD, but somehow this spot feels like a secret – probably because most people walking past have no idea there’s this incredible private terrace situation happening above their heads.

The harbor view is honestly the star here, and I’m not just saying that because it’s in the name. From up there, you can watch the ferries doing their thing between Circular Quay and the North Shore, and if you time it right (around sunset, obviously), the whole Opera House and Bridge setup looks like someone’s showing off. The rooftop itself is actually well thought out – not just some afterthought deck with plastic chairs. They’ve got proper seating, some shade options, and honestly, it’s where I ended up having my morning coffee every single day instead of rushing out to explore. Which, for someone who usually can’t sit still on vacation, says something.

Location-wise, you’re walking distance to everything that matters. Wynyard Station is maybe three minutes away, so getting around is dead easy. The Observatory Hotel is just down the street if you want to feel fancy for a drink, and you’re close enough to The Rocks that you can actually walk there without dealing with transport – though I’d recommend the long way around through the Botanic Gardens if you’ve got time. One thing I appreciated was how quiet it stays at night, considering you’re basically in the heart of everything. High Street doesn’t get the late-night foot traffic that some of the other CBD streets do, so you can actually sleep with the windows open if you want that harbor breeze.

The place itself feels more like staying at a friend’s well-appointed apartment than a typical hotel experience. Check-in was smooth – no lobby drama or waiting around – and the space has that lived-in quality that makes you comfortable immediately. The kitchen actually works (shocking, I know), so you can grab supplies from the IGA down the street or the weekend markets and not feel like you’re cooking in a toy kitchen. Storage is decent too, which matters when you’re staying more than a couple nights.

What really sets this apart is how it hits that sweet spot between being right in the middle of everything but still feeling like you have your own space. The 8.9 rating makes sense – it’s not trying to be the fanciest place in Sydney, but it nails the things that actually matter when you’re staying somewhere. The rooftop alone is worth the price difference from a standard hotel room, especially if you’re the type who likes having somewhere to decompress after a day of playing tourist. Just don’t expect room service or a concierge – this is more about having a genuinely great base to explore from, with one of the better private outdoor spaces you’ll find in the CBD.

Rooms

• Estimated price from: $671. Two-Bedroom Apartment with 2 × 1 double bed for Max persons: 4

Reviews

• Fabulous – Paula from New Zealand – 12 June 2025 (10/10)

  The location was fantastic especially with Vivid on.

• Superb – Simon from Australia – 3 June 2025 (9/10)

  We were let down by our previous accommodation and found this loveley little cottage. It was clean ancomfortable and was near to the city centre with a view of the harbour and vivid Sydney.
  
  What could be improved: It was all perfect thankyou

• Excellent property, our group loved sitting on the verandah and watching the boats on the harbour – Karen from Australia – 2 June 2025 (9/10)

  Very comfortable two bedroom cottage in historic Milsons Point. A recent renovation has updated the interior feel of the property. Great location opposite Barangaroo shops, restaurants and train and ferry stations though a little walking is required. Easy walking to The Rocks, Circular Quay

• Helpfully Located Sydney Unit – Chelsea from Australia – 2 June 2025 (8/10)

  Location is perfect for getting around the city, great spot for people new to the area, close to the major things you want to see! Beds are really comfortable as well which ensures a great sleep after a long day.

• Very good location for tourists to experience Sydney. – Joanne from United Kingdom – 26 April 2025 (9/10)

  Good location and an interesting older property.
  
  What could be improved: Older doors and windows allowed every noise from outside to be heard – this was significant and disturbed our sleep.

• It was a wonderful holiday for our family in a beautiful home – Jane from Australia – 10 March 2025 (9/10)

  The location was excellent. We loved the terrace and the sea view. Could have sat there all day looking out. It was also super quiet.
  
  What could be improved: I prefer a quilt cover than sheets either side of the quilt.

• Exceptional – Adam from Australia – 8 March 2025 (10/10)

  The property is modern and well appointed. It was in a quiet spot and we could get around really well. It was perfect for 4 of us and there was an extra bed if needed (we didn't). Beds were comfortable. It was great having a room with a view of the water.
  
  What could be improved: Not really that we didn't like, but having an extra bath mat or two would be great! Otherwise ant fault the place!!

• This location made it a breeze to get anywhere by foot, we would definitely stay here again – Kalleina from Australia – 22 February 2025 (10/10)

  Fantastic location, great views
  
  What could be improved: There wasn’t anything we didn’t like

• Very enjoyable. Highly recommended – Alicia from Australia – 27 January 2025 (10/10)

  Clean, kitchen well stocked, great location, very attentive hosts.
  
  What could be improved: As it is an old building the front stairs’ step are narrow and one has to be careful when carrying luggage

• Beautiful stay thank you will definitely recommend to my friends – Raja from United Kingdom – 1 January 2025 (10/10)

  Great location spacious place
  
  What could be improved: Parking charges

SURROUNDINGS

Facilities