Windsor Vacations from $1,392
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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 $1,691, price is now $1,392 per person
$1,392
per person
Nov 10 - Nov 13
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Sydney (SYD)
8.2/10 Very Good! (1,000 reviews)
Small room, good for short stay, reasonable walk to L2/3 on George St.
Reviewed on Aug 20, 2025
YEHS Hotel Sydney Harbour Suites
Sydney Central Business District
Price was $2,431, price is now $2,041 per person
$2,041
per person
Oct 6 - Oct 11
found 5 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sydney (SYD)
8.2/10 Very Good! (2,225 reviews)
Enjoyed my stay, I wanted to use the full suite of gym and leisure facilities but the sauna and some equipment was out of order.
Reviewed on Aug 24, 2025
Coogee Bay Boutique Hotel
Coogee
Price was $2,221, price is now $1,876 per person
$1,876
per person
Nov 12 - Nov 16
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Sydney (SYD)
8.8/10 Excellent! (824 reviews)
Great location. Spacious, clean room with a beautiful view. Everything within walking distance. Plenty of food options around. The beach is right across the street
Reviewed on Aug 16, 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
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
$117 nightly
The price is $129 total per night from Sep 4 to Sep 5
$129 total
Sep 4 - Sep 5
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
"Great hotel good shower and breakfast"
Reviewed on Aug 15, 2025
Tates Hotel Windsor
335 George St, Windsor, NSW
5.8/10 (71 reviews)
Comfortable to stay at
"Initially went past then found entrance off a side street. Quick book in. Parking availability limited.Nice bistro"
Reviewed on Jul 11, 2025
Windsor Riverview Inn
47 George Street, Windsor, NSW
$86 nightly
The price is $97 total per night from Aug 26 to Aug 27
$97 total
Aug 26 - Aug 27
Total with taxes and fees
6.6/10 (318 reviews)
"the shower was hot and the bed was comfortable"
Reviewed on Apr 14, 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
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
Blue Mountains Adventure: Scenic World, Zoo & Koala Photo
$143
per adult
88% of travellers recommend
Big Bus Sydney Hop-On Hop-Off Sightseeing Tour
$38
per adult
86% of travellers recommend
Sydney: Blue Mountains National Park Tour with River Cruise
$64
per adult
100% 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.