Windsor Vacations from $1,216
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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.
APX Darling Harbour
Sydney Central Business District
Price was $1,515, price is now $1,216 per person
$1,216
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Sydney (SYD)
7.6/10 Good! (1,001 reviews)
Room was great, huge bed,location amazing but the men front of house, not that happy or helpful
Reviewed on Jan 6, 2026
YEHS Hotel Sydney Harbour Suites
Sydney Central Business District
Price was $1,811, price is now $1,460 per person
$1,460
per person
Apr 15 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sydney (SYD)
8.2/10 Very Good! (2,388 reviews)
Conveniently close to Darling Harbor. Friendly and helpful staff.
Reviewed on Jan 21, 2026
InterContinental Sydney Double Bay by IHG
Double Bay
Price was $1,923, price is now $1,631 per person
$1,631
per person
Apr 15 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sydney (SYD)
9/10 Wonderful! (596 reviews)
Initial room was sub standard with mol
Reviewed on Dec 13, 2025
Rydges Australia Square
Sydney Central Business District
Price was $1,788, price is now $1,522 per person
$1,522
per person
Apr 15 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sydney (SYD)
9.2/10 Wonderful! (1,714 reviews)
The room was really small but it was clean and comfortable. It was in a good location; we could walk to many places.
Reviewed on Jan 21, 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
$121 nightly
The price is $133 total per night from Jan 26 to Jan 27
$133 total
Jan 26 - Jan 27
Total with taxes and fees
8.8/10 Excellent! (1,000 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
$75 nightly
The price is $82 total per night from Jan 25 to Jan 26
$82 total
Jan 25 - Jan 26
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
$494 nightly
The price is $494 total per night from Jan 26 to Jan 27
$494 total
Jan 26 - Jan 27
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
Flanked by the Opera House and Harbour Bridge, Sydney’s transportation hub is one of the prettiest terminals in the world.
Sydney Opera House
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
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
$132
per adult
76% of travellers recommend
Sydney Harbour Sightseeing Cruise Morning or Afternoon Departure
$37
per adult
96% of travellers recommend
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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.