Windsor Vacation Packages 2026 from $1,387

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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

$1,387

per person

Nov 14 - Nov 18

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Sydney (SYD)

8.4/10 Very Good! (1,005 reviews)

Fabulous location. Close to trains and food. Easy walk to darling harbour. Very comfortable bed. Free bottled water in room. Nice bathroom. Staff very pleasant and helpful

Reviewed on Oct 3, 2026

YEHS Hotel Sydney Harbour Suites

Sydney Central Business District

$2,075

per person

Dec 12 - Dec 17

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Sydney (SYD)

8.2/10 Very Good! (2,960 reviews)

It is very old and outdated. The only pros is it’s location

Reviewed on Oct 3, 2026

Mariners Court Hotel Sydney

Woolloomooloo

$1,463

per person

Nov 20 - Nov 25

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Sydney (SYD)

8.6/10 Excellent! (1,005 reviews)

Delicious breakfast, friendly staff and well located affordable accommodation

Reviewed on Sep 27, 2026

YEHS Hotel Sydney QVB

Sydney Central Business District

$1,983

per person

Nov 22 - Nov 26

found 6 hours ago

Roundtrip non-stop flight included

Chicago (CHI) to Sydney (SYD)

8.6/10 Excellent! (1,002 reviews)

La habitación es pequeña pero el hotel está fabuloso, muy limpio todo, la ropa de cama y toallas nuevas, el personal muy amable, está frente al Queen Victoria Building y puede tomarse metro, camión o tram caminando 2 min, catedral está a 3 cuadras y la zona nunca se queda sola, tienes súper enfrente por cualquier urgencia, puedes descansar super bien, no es un hotel de mochileros, me encantó

Reviewed on Oct 3, 2026

The Darling at the Star

Pyrmont

$2,327

per person

Dec 12 - Dec 17

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Sydney (SYD)

9.6/10 Exceptional! (1,002 reviews)

Great!

Reviewed on Oct 3, 2026

Where to stay in Windsor

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

A tree in a grassy field with horses grazing nearby.

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 Hawkins Lookout.

A river with a bridge, a forested island, and boats.

Dangar Island

Travelers like the parks in Dangar Island, and Brisbane Water National Park is a top attraction you might want to visit.

Berowra Waters

While visiting Berowra Waters, you might make a stop by sights like Berowra Waters Marina and Muogamarra Nature Reserve.

An aerial view of a coastal area with a bridge, dense forests, and a small island with buildings.

Kurrajong

Travelers like the parks in Kurrajong, and Wollemi National Park is a top attraction you might want to visit.

A large steel bridge spanning a wide river with multiple supports.

Canoelands

Travelers like the parks in Canoelands, and Brisbane Water National Park is a top attraction you might want to visit.

Windsor Hotel Deals

Crowne Plaza Hawkesbury Valley by IHG

61 Hawkesbury Valley Way Windsor NSW

Fully refundable

$126 nightly

$138 total

Oct 25 - Oct 26

Total with taxes and fees

9/10 Wonderful! (1,000 reviews)

"We love this place"

Reviewed on Sep 27, 2026

Windsor Heritage Motel

54 George Street Windsor NSW

$71 nightly

$79 total

Oct 17 - Oct 18

Total with taxes and fees

5.2/10 (311 reviews)

"The room was dirty , the airconditioner n"

Reviewed on Sep 22, 2026

Windsor Riverview Inn

47 George Street Windsor NSW

$93 nightly

$104 total

Oct 19 - Oct 20

Total with taxes and fees

6.6/10 (329 reviews)

"Way overpriced for poor service, smelly…very smelly room. Convenient location but have traffic all night over bridge. Shower was okay and clean sheets."

Reviewed on Sep 25, 2026

See all 676 properties in Windsor

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.