Windsor Vacations from $1,263
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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 CBD
Sydney Central Business District
Price was $1,689, price is now $1,263 per person
$1,263
per person
Jul 1 - Jul 6
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Sydney (SYD)
8.2/10 Very Good! (1,006 reviews)
Great location at CBD. Close to everything. As a female solo traveler, safety and convenience are my top priorities. This hotel works. My room was small and there is no view. My window faces another wall. But I don’t mind. The room was quiet and I got good rest after each day’s outing. No complaints.
Reviewed on Apr 30, 2026
Quest North Sydney
North Sydney
Price was $1,903, price is now $1,615 per person
$1,615
per person
Aug 2 - Aug 8
found 13 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Sydney (SYD)
9.2/10 Wonderful! (374 reviews)
Amenities, proximity to public transportation, kitchen, big closets, great shower.
Reviewed on Jan 25, 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 Hawkesbury River or Dharug National Park.
Windsor Hotel Deals
Crowne Plaza Hawkesbury Valley by IHG
61 Hawkesbury Valley Way Windsor NSW
Fully refundable
$125 nightly
The price is $138 total per night from Jun 8 to Jun 9
$138 total
Jun 8 - Jun 9
Total with taxes and fees
9/10 Wonderful! (1,000 reviews)
Great location, lovely surrounds, great service, great food.
Reviewed on May 8, 2026
Windsor Riverview Inn
47 George Street Windsor NSW
$97 nightly
The price is $107 total per night from May 22 to May 23
$107 total
May 22 - May 23
Total with taxes and fees
6.6/10 (326 reviews)
Room was clean. Tv worked but could only access Network 10 channels only. Very disappointing.
Reviewed on May 3, 2026
Windsor Heritage Motel
54 George Street Windsor NSW
$81 nightly
The price is $89 total per night from Jun 4 to Jun 5
$89 total
Jun 4 - Jun 5
Total with taxes and fees
5.2/10 (300 reviews)
Lots of cockroaches and glues onside of the room where we stayed. The towels are worn out. The floor looks terrible.
Reviewed on Apr 24, 2026
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
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.
Circular Quay
Flanked by the Opera House and Harbour Bridge, Sydney’s transportation hub is one of the prettiest terminals in the world.
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 Official Guided Walking Tour
$36
per adult
96% of travellers recommend
Sydney Harbour Cultural Cruise with Island Stop
$60
per adult
Sydney Harbour Sightseeing Cruise Morning or Afternoon Departure
$43
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.