Title: Book the Best HISTORIC Hotels in Woolloomooloo in 2026 | Expedia.ca [Woolloomooloo Travel Guide](https://expedia.ca/Sydney-Woolloomooloo.dx10765)[Vacation Rentals in Sydney](https://expedia.ca/Sydney-Vacation-Rentals.d178312.Travel-Guide-VacationRentals)[Flights to Sydney](https://expedia.ca/Cheap-Flights-To-Sydney.d178312.Travel-Guide-Flights)[Things to do in Sydney](https://expedia.ca/Things-To-Do-In-Sydney.d178312.Travel-Guide-Activities)[Woolloomooloo Car Rentals](https://expedia.ca/Car-Rentals-In-Woolloomooloo.d10765.Car-Rental-Guide)[Woolloomooloo Vacations](https://expedia.ca/Woolloomooloo.d10765.Destination-Travel-Guides) ![Woolloomooloo](https://images.trvl-media.com/place/10765/e380d3f9-9346-49d2-8f12-2c8c3320e623.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/10765/e380d3f9-9346-49d2-8f12-2c8c3320e623.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Woolloomooloo Historic Hotels Tonight [Mar 14 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=10765&startDate=2026-03-14&endDate=2026-03-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 15 - Mar 16](https://www.expedia.ca/Hotel-Search?regionId=10765&startDate=2026-03-15&endDate=2026-03-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=10765&startDate=2026-03-20&endDate=2026-03-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=10765&startDate=2026-03-27&endDate=2026-03-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Woolloomooloo historic hotels ![Exterior](https://images.trvl-media.com/lodging/34000000/33690000/33681800/33681763/w1920h1279x0y0-ac557785.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/34000000/33690000/33681800/33681763/25b9a459.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33690000/33681800/33681763/d94e7190.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/34000000/33690000/33681800/33681763/e6fc6ab8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spectacular Location Overlooking Sydney Harbour from a Unique & Historic Setting [](https://www.expedia.ca/Sydney-Hotels-Spectacular-Location-Overlooking-Sydney-Harbour-From-A-Unique-Historic-Setting.h33681763.Hotel-Information) Millers Point 9.6/10 Exceptional (304 reviews) "We had a wonderful stay, the accomodation was perfect for our family of 4, clean and comfy, and the best location, would definitely stay here again when in Sydney, thank you " ![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg) Veronika F. CA $290 CA $549 total includes taxes & fees Mar 17 - Mar 18 [](https://www.expedia.ca/Sydney-Hotels-Spectacular-Location-Overlooking-Sydney-Harbour-From-A-Unique-Historic-Setting.h33681763.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/74000000/73640000/73636400/73636313/w1920h1279x0y0-6daf2454.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/74000000/73640000/73636400/73636313/0d578c3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/74000000/73640000/73636400/73636313/41e1ecc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73640000/73636400/73636313/f69b0905.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spectacular Harbour Peninsular Location with a Unique Historic Village Setting. [](https://www.expedia.ca/Sydney-Hotels-Spectacular-Location-Overlooking-Sydney-Harbour-From-A-Unique-Historic-Setting.h73636313.Hotel-Information) Millers Point 9.8/10 Exceptional (126 reviews) "Great location Sam was very helpful Everything we needed for our stay Would definitely recommend " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Mark M. CA $278 CA $512 total includes taxes & fees Mar 19 - Mar 20 [](https://www.expedia.ca/Sydney-Hotels-Spectacular-Location-Overlooking-Sydney-Harbour-From-A-Unique-Historic-Setting.h73636313.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/96000000/95110000/95107000/95106922/2301abe6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/96000000/95110000/95107000/95106922/1a48791f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/96000000/95110000/95107000/95106922/c48f7fb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/96000000/95110000/95107000/95106922/0be0d1f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Citadines Walker North Sydney [](https://www.expedia.ca/Sydney-Hotels-Citadines-Walker-North-Sydney.h95106922.Hotel-Information) North Sydney 9.0/10 Wonderful (687 reviews) "Clean Room, friendly staff, excellent location close to eateries and transport options." ![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg) Sundeep CA $165 CA $181 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Sydney-Hotels-Citadines-Walker-North-Sydney.h95106922.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-03-28&endDate=2026-03-29®ionId=10765&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Price trends for hotels in Woolloomooloo | Less expensive | More expensive | This month | Next month | | -------------- | -------------- | ---------- | ---------- | | May | December | CA $219 | CA $170 | | Month | Price | | --------- | ------- | | January | CA $235 | | February | CA $263 | | March | CA $219 | | April | CA $170 | | May | CA $168 | | June | CA $171 | | July | CA $171 | | August | CA $217 | | September | CA $203 | | October | CA $261 | | November | CA $248 | | December | CA $274 | Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed hotels in Woolloomooloo. Select dates and complete search for nightly totals inclusive of taxes and fees. ## Top Woolloomooloo Hotel Reviews ![Paradox Sydney](https://images.trvl-media.com/lodging/1000000/570000/564600/564600/05890585_y.jpg) ### Paradox Sydney 10/10 Excellent "Great location and excellent bathroom" [](https://expedia.ca/Sydney-Hotels-Paradox-Sydney.h564600.Hotel-Information) ![PARKROYAL Darling Harbour, Sydney](https://images.trvl-media.com/lodging/1000000/30000/22600/22576/fe55f674_y.jpg) ### PARKROYAL Darling Harbour, Sydney 10/10 Excellent "Close to walking distance to Darling Harbour and the lower end of the CBD. Very clean, staff friendly, courteous, and obliging, food well prepared and tasty, rooms very clean and well appointed - highly recommend." [](https://expedia.ca/Sydney-Hotels-PARKROYAL-Darling-Harbour.h22576.Hotel-Information) ![The Grace Hotel](https://images.trvl-media.com/lodging/1000000/470000/460400/460380/e4b94ad8_y.jpg) ### The Grace Hotel 10/10 Excellent "Stayed quite a few times previously, will stay again very soon." [](https://expedia.ca/Sydney-Hotels-The-Grace-Hotel.h460380.Hotel-Information) ![Four Seasons Hotel Sydney](https://images.trvl-media.com/lodging/1000000/10000/2300/2220/11f73159_y.jpg) ### Four Seasons Hotel Sydney 10/10 Excellent "Room was great. Fabulous window seat with glimpses of the harbour bridge. Staff were very friendly" [](https://expedia.ca/Sydney-Hotels-Four-Seasons-Hotel-Sydney.h2220.Hotel-Information) ![The Fullerton Hotel Sydney](https://images.trvl-media.com/lodging/1000000/290000/284400/284308/6aa7dc33_y.jpg) ### The Fullerton Hotel Sydney 10/10 Excellent "Great location in the CBD, a modern 5 star hotel with historic highlights of the old GPO " [](https://expedia.ca/Sydney-Hotels-The-Fullerton-Hotel-Sydney.h284308.Hotel-Information) ![Rydges Sydney Airport Hotel](https://images.trvl-media.com/lodging/6000000/5940000/5932400/5932305/dd75ee82_y.jpg) ### Rydges Sydney Airport Hotel 8/10 Good "Very convenient for the international terminal at Melbourne Airport. Reception staff friendly and efficient. Room clean and bed comfortable. Bathroom arrangements unusual, with separate w.c. and shower room. Hand basin in the bedroom. Being close to the airport there was a smell of aviation fuel in the bedroom, which was not pleasant. (Window closed)." [](https://expedia.ca/Sydney-Hotels-Rydges-Sydney-Airport-Hotel.h5932305.Hotel-Information) ![YEHS Hotel Sydney Harbour Suites](https://images.trvl-media.com/lodging/1000000/430000/426200/426104/144baa87_y.jpg) ### YEHS Hotel Sydney Harbour Suites 8/10 Good "The room was decent with modern touches. There is a slight smell when you run the water initially but then goes away. There hotel is in a great location and the staff are very friendly (Thank you Mild)" [](https://expedia.ca/Sydney-Hotels-YEHS-Hotel-Sydney-Harbour-Suites.h426104.Hotel-Information) ![Mercure Sydney](https://images.trvl-media.com/lodging/1000000/470000/460500/460470/d2aceae8_y.jpg) ### Mercure Sydney 2/10 Terrible "Very poor customer service. Unfair treatment." [](https://expedia.ca/Sydney-Hotels-Mercure-Sydney.h460470.Hotel-Information) ![Hyatt Regency Sydney](https://images.trvl-media.com/lodging/1000000/20000/15900/15886/c4f7df02_y.jpg) ### Hyatt Regency Sydney 6/10 Okay "The check in was not welcoming and it felt like they were doing us a favour. Check in was 3pm and we were emailed to advise our room was available an hour early so that was appreciated. P" [](https://expedia.ca/Sydney-Hotels-Hyatt-Regency-Sydney.h15886.Hotel-Information) ## Frequently asked questions ### What should I expect on my historical trip to Woolloomooloo? ### How many historically relevant hotels are there in Woolloomooloo? ### What are the most important historical sites and other places to visit in Woolloomooloo? ### What is a historic hotel like in Woolloomooloo? ### What is the difference between a historic hotel and a heritage hotel? ### Do historic hotels in Woolloomooloo have modern facilities? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [4 Star Hotels in Sydney ](https://www.expedia.ca/4Star-Sydney-Hotels.s40-0-d178312.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Sydney ](https://www.expedia.ca/5Star-Sydney-Hotels.s50-0-d178312.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Blue Mountains ](https://www.expedia.ca/Blue-Mountains-Hotels-Hotel-With-Early-Check-In.0-0-d6035338-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - 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