Windsor Vacations from $1,902
Book a Hotel + Flight or Car together to unlock savings
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 $2,277, price is now $1,902 per person
$1,902
per person
Nov 17 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Sydney (SYD)
7.6/10 Good! (1,010 reviews)
Second time staying here and will stay again. Friendly staff, very convenient location at darling harbour. Comfortable rooms
Reviewed on Oct 5, 2025
Furama Darling Harbour
Haymarket
Price was $2,462, price is now $2,141 per person
$2,141
per person
Nov 17 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Sydney (SYD)
8.4/10 Very Good! (1,001 reviews)
This is my 3rd time staying here and would stay again as locations very convenient.
Reviewed on Oct 6, 2025
Rydges Darling Square Apartment Hotel
Sydney Central Business District
Price was $2,372, price is now $2,067 per person
$2,067
per person
Nov 17 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Sydney (SYD)
8.8/10 Excellent! (1,478 reviews)
Great property. We usually stay Darling Harbour but opted to try this...much easier access to transport, and still walking distance to Darling Harbour & Chinatown for dining.
Reviewed on Oct 8, 2025
The Ultimo
Haymarket
Price was $2,338, price is now $2,045 per person
$2,045
per person
Nov 17 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Sydney (SYD)
8.8/10 Excellent! (1,001 reviews)
Great Hotel and staff - but lots of noisy building work going on while we were there and the lifts were out of order. Also had to request the air conditioning to our room was turned on each day.
Reviewed on Sep 3, 2025
Where to stay in Windsor
Find the best Windsor areas and neighborhoods for the activities you enjoy most. Learn more about Windsor
Sydney Central Business District
2 out of top 10 points of interest in this area
4.5/5(1,320 area reviews)
Historical and commercial heart of Sydney, the CBD boasts towering skyscrapers, lively café culture, and nightlife in areas like Darling Harbour. Explore parks such as Hyde Park and cultural institutions, while enjoying easy access to public transport.
Windsor Hotel Deals
Crowne Plaza Hawkesbury Valley by IHG
61 Hawkesbury Valley Way, Windsor, NSW
Fully refundable
$119 nightly
The price is $131 total per night from Oct 12 to Oct 13
$131 total
Oct 12 - Oct 13
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
"Clean and tidy, good staff and amenities."
Reviewed on Sep 20, 2025
Windsor Riverview Inn
47 George Street, Windsor, NSW
$95 nightly
The price is $105 total per night from Oct 24 to Oct 25
$105 total
Oct 24 - Oct 25
Total with taxes and fees
6.6/10 (319 reviews)
"the shower was hot and the bed was comfortable"
Reviewed on Apr 14, 2025
Windsor Heritage Motel
54 George Street, Windsor, NSW
$75 nightly
The price is $83 total per night from Oct 22 to Oct 23
$83 total
Oct 22 - Oct 23
Total with taxes and fees
5.2/10 (292 reviews)
"The motel is basic but suitable for my need."
Reviewed on Sep 18, 2025
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
Big Bus Sydney Hop-On Hop-Off Sightseeing Tour by Open-Top Bus
$39
per adult
86% of travellers recommend
Taronga Zoo Ticket with Hop-On Hop-Off Sydney Harbour Explorer Cruise
$54
per adult
88% of travellers recommend
Sydney Attractions Pass including SEA LIFE Sydney Aquarium
$34
per adult
84% of travellers recommend
Explore a world of travel with Expedia
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.