Windsor Vacations from $1,181
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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.
YEHS Hotel Sydney Harbour Suites
Sydney Central Business District
Price was $1,907, price is now $1,448 per person
$1,448
per person
Feb 19 - Feb 23
found 2 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sydney (SYD)
8.2/10 Very Good! (2,388 reviews)
Front desk staff were great - helpful and efficient.
Reviewed on Jan 12, 2026
InterContinental Sydney Double Bay by IHG
Double Bay
Price was $2,825, price is now $2,237 per person
$2,237
per person
Feb 16 - Feb 21
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Sydney (SYD)
9/10 Wonderful! (596 reviews)
Initial room was sub standard with mol
Reviewed on Dec 13, 2025
APX Darling Harbour
Sydney Central Business District
Price was $2,227, price is now $1,775 per person
$1,775
per person
Feb 16 - Feb 21
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) 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
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 18 to Jan 19
$130 total
Jan 18 - Jan 19
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
Clean rooms. Friendly service. Excellent breakfast.
Reviewed on Jan 2, 2026
Windsor Heritage Motel
54 George Street Windsor NSW
Fully refundableReserve now, pay when you stay
$78 nightly
The price is $86 total per night from Jan 23 to Jan 24
$86 total
Jan 23 - Jan 24
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
$460 nightly
The price is $460 total per night from Jan 15 to Jan 16
$460 total
Jan 15 - Jan 16
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
Taronga Zoo Ticket with Sydney Harbour Ferry Return
$50
per adult
84% of travellers recommend
From Sydney: Port Stephens Dolphin, Koalas, Lunch & Sandboarding
$148
per adult
80% 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.