A bird in flight over water.

Windsor Vacations from $2,031

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.
  • Jan 23 - Jan 31

    Sofitel Sydney Darling Harbour + Flight

    Sydney Central Business District
    6 nights
    5.0 star property
    9.0/10 - Wonderful (1,003 reviews)
    "Great location, good room with views."
    Reviewed November 6, 2026
    Roundtrip • Dallas (DFW) - Sydney (SYD)
    DFW - SYD • 1 stop SYD - DFW • 2 stops
    $2,387
    $2,031
    per traveler
    found 2 hours ago
    Sofitel Sydney Darling Harbour
  • Jan 23 - Jan 31

    Harbour Rocks by Ode Hotels + Flight

    The Rocks
    6 nights
    5.0 star property
    8.6/10 - Excellent (1,000 reviews)
    "This hotel is in a fantastic location and it is a very nice hotel but it should not be billed as a 5 star luxury hotel. It is really a 3.5 star hotel. The biggest complaints are no elevator, they do have a dumb waiter for bags. The windows are single pane (barely). When people walk ups and down the Suez Canal or Nurses walk you can hear every conversation. There is a bar behind the property that gets loud as well. Next is no bottled water but the staff did tell me I could feel free to..."
    Reviewed November 5, 2026
    Roundtrip • Dallas (DFW) - Sydney (SYD)
    DFW - SYD • 1 stop SYD - DFW • 2 stops
    $2,902
    $2,215
    per traveler
    found 2 hours ago
    Harbour Rocks by Ode Hotels
  • Jan 23 - Jan 31

    Sofitel Sydney Wentworth + Flight

    Sydney Central Business District
    6 nights
    5.0 star property
    8.8/10 - Excellent (237 reviews)
    "Very helpful staff"
    Reviewed November 6, 2026
    Roundtrip • Dallas (DFW) - Sydney (SYD)
    DFW - SYD • 1 stop SYD - DFW • 2 stops
    $2,507
    $2,107
    per traveler
    found 2 hours ago
    Sofitel Sydney Wentworth
  • Dec 16 - Dec 23

    YEHS Hotel Sydney QVB + Flight

    Sydney Central Business District
    5 nights
    3.5 star property
    8.4/10 - Very good (1,001 reviews)
    "Hotel in good location close to shops and public transport. Easy access to airport by train. Room was sparse but clean and comfortable with basic amenities."
    Reviewed November 3, 2026
    Roundtrip • Dallas (DFW) - Sydney (SYD)
    DFW - SYD • 1 stop SYD - DFW • 1 stop
    $2,552
    $2,158
    per traveler
    found 19 hours ago
    YEHS Hotel Sydney QVB
  • Jan 23 - Jan 31

    Establishment Hotel + Flight

    Sydney Central Business District
    6 nights
    5.0 star property
    9.0/10 - Wonderful (707 reviews)
    Roundtrip • Dallas (DFW) - Sydney (SYD)
    DFW - SYD • 1 stop SYD - DFW • 2 stops
    $2,415
    $2,049
    per traveler
    found 2 hours ago
    Establishment Hotel

Where to stay in Windsor

Find the best Windsor areas and neighborhoods for the activities you enjoy most. Learn more about Windsor
Learn more about Windsor

Sydney Central Business District

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.

Darling Harbour

Adjacent to Sydney's city centre, Darling Harbour boasts a pedestrian precinct with attractions like the Australian National Maritime Museum and Chinese Garden of Friendship. Enjoy dining at Cockle Bay Wharf, explore Tumbalong Park, and access various transport options, including the Inner West Light Rail and ferry services.

Sydney Olympic Park

Featuring a large sports and entertainment area, commercial developments, and extensive parklands, this Greater Western Sydney suburb offers attractions like Bicentennial Park and Newington Armory. Easily accessible via Olympic Park railway line and ferry services.

Bondi Beach

See a perfect example of the Australian beach lifestyle in this famous Sydney neighborhood with ocean pools, excellent surf and a bustling brunch scene.

Manly

Beach-side suburb with easy ferry access, Manly offers a mix of ocean and harbor beaches, scenic cycle tracks, and a lively commercial area along The Corso. Explore historic sites like North Head Quarantine Station and enjoy outdoor dining.

Discover the most popular places to visit in Windsor

What to do near Windsor

Windsor Hotel Deals

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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.