Windsor Vacations from $1,770
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Your Windsor Vacation
Book a vacation package to Windsor and immerse yourself in everything this fishing neighborhood has to offer. With a reputation for watersports, cycling and culture, your next great adventure is waiting for you here. Eager to explore the sights during your trip to Windsor? Make sure you check out nearby attractions such as Hawkesbury River, Hawkesbury Race Club and Lynwood Country Club. No matter your travel plans or budget, booking your dream Windsor vacation is simple with Expedia.
The Latest Windsor Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Courthouse Hotel
Darlinghurst
Price was $3,060, price is now $1,770 per person
$1,770
per person
Apr 3 - Apr 7
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Sydney (SYD)
7.4/10 Good! (42 reviews)
Great staff & no troubles with accommodation, it is old, but i love old, it is tidy & comfortable..
The atmosphere of the place is awesome with a great view over oxford st..
My only problem with the whole stay is, there is no parking at all & as far as im concerned, if you pay for a room, you get a space for your car aswell, city or not..
Reviewed on Dec 16, 2025
25hours Hotel Sydney The Olympia
Paddington
Price was $3,338, price is now $1,957 per person
$1,957
per person
Apr 3 - Apr 7
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Sydney (SYD)
10/10 Exceptional! (4 reviews)
What a delightful respite from the heatwave outside. The funky design elements make the room really stand out without being offensive. The staff were super friendly and helpful. Comfortable bed and great shower! Also of note are the fabulous rooftop bar and Palomar restaurant which was pure 'chef's kiss'.
Reviewed on Jan 11, 2026
Kith Hotel
Pyrmont
Price was $3,168, price is now $1,861 per person
$1,861
per person
Apr 3 - Apr 7
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Sydney (SYD)
8.8/10 Excellent! (390 reviews)
Hotel was exactly what we needed for a stay in darling harbour! Shout out to Sophie on the front desk who was so friendly and welcoming! Great Service!
Reviewed on Jan 11, 2026
Coogee Bay Boutique Hotel
Coogee
Price was $3,511, price is now $2,084 per person
$2,084
per person
Apr 3 - Apr 7
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Sydney (SYD)
8.8/10 Excellent! (836 reviews)
Yes air conditioner will work clean my staff very helpful
Reviewed on Jan 15, 2026
Where to stay in Windsor
Find the best Windsor areas and neighborhoods for the activities you enjoy most. Learn more about Windsor
Wisemans Ferry
You'll enjoy the cafes and riverfront in Wisemans Ferry. You might want to make time for a stop at Dharug National Park or Hawkesbury River.
Windsor Hotel Deals
Crowne Plaza Hawkesbury Valley by IHG
61 Hawkesbury Valley Way Windsor NSW
Fully refundable
$118 nightly
The price is $130 total per night from Jan 21 to Jan 22
$130 total
Jan 21 - Jan 22
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
Our stay was wonderful the rooms were perfect, the adult pool was amazing, the staff went above & beyond to cater for all of our needs, definently staying again, thank you.
Reviewed on Jan 11, 2026
Windsor Heritage Motel
54 George Street Windsor NSW
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $84 total per night from Jan 18 to Jan 19
$84 total
Jan 18 - Jan 19
Total with taxes and fees
5.2/10 (294 reviews)
The motel is basic but suitable for my need.
Reviewed on Sep 18, 2025
Luxury House 5 Bedrooms River View
Windsor NSW
$485 nightly
The price is $485 total per night from Jan 19 to Jan 20
$485 total
Jan 19 - Jan 20
Total with taxes and fees
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.
Discover the most popular places to visit in Windsor
Circular Quay
4.5/5(1,399 reviews)
Flanked by the Opera House and Harbour Bridge, Sydney’s transportation hub is one of the prettiest terminals in the world.
Sydney Opera House
4.5/5(1,512 reviews)
One of the world’s most famous buildings is surprisingly accessible; take in a show or just take a stroll to admire this astonishing building.
Sydney Harbour Bridge
4.5/5(1,379 reviews)
Stroll from end-to-end or climb to the top; either way, Sydney’s “Coat Hanger” serves up memories to last a lifetime.
Things to do
Sydney Opera House Tour & Dine Experience
$59
per adult
96% of travellers recommend
From Sydney: Port Stephens Dolphin, Koalas, Lunch & Sandboarding
$148
per adult
80% of travellers recommend
Sydney Harbour Sightseeing Cruise Morning or Afternoon Departure
$37
per adult
96% of travellers recommend
Explore a world of travel with Expedia
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.