Windsor Vacation Packages 2026 from $1,720

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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.

Easy Beach Access From Tranquil Retreat

Curl Curl

$1,720

per person

Oct 22 - Oct 27

found 20 hours ago

Roundtrip non-stop flight included

Chicago (CHI) to Sydney (SYD)

No reviews

YEHS Hotel Sydney CBD

Sydney Central Business District

$1,725

per person

Oct 22 - Oct 27

found 20 hours ago

Roundtrip non-stop flight included

Chicago (CHI) to Sydney (SYD)

8.4/10 Very Good! (1,000 reviews)

Seaside Retreat With Parking and Balcony

Newport

$1,846

per person

Oct 24 - Oct 27

found 1 hour ago

Roundtrip non-stop flight included

Chicago (CHI) to Sydney (SYD)

No reviews

Luxury 2-bed With Ocean Views and Garden

Collaroy

$1,744

per person

Oct 24 - Oct 27

found 15 hours ago

Roundtrip non-stop flight included

Chicago (CHI) to Sydney (SYD)

No reviews

Spacious 3-bed Apartment in the Heart of St Ives

St Ives

$1,760

per person

Oct 22 - Oct 27

found 20 hours ago

Roundtrip non-stop flight included

Chicago (CHI) to Sydney (SYD)

No reviews

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 Marramarra National Park.

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 calm lake with several boats, a bridge, and hills in the background.

North Richmond

Travelers like the parks in North Richmond, and Hawkesbury River 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

$123 nightly

$135 total

Sep 27 - Sep 28

Total with taxes and fees

9/10 Wonderful! (1,000 reviews)

"Clean renovated room. Above expectations for breakfast for type of hotel. Kids loved the Nutella pancakes and great to have ordering of egg plates and good size coffees made to order. Beautiful surroundings around hotel. Older building though still causing issues with fire alarm going off and speakers ..."

Reviewed on Sep 13, 2026

Windsor Heritage Motel

54 George Street Windsor NSW

$73 nightly

$82 total

Sep 20 - Sep 21

Total with taxes and fees

Windsor Riverview Inn

47 George Street Windsor NSW

$95 nightly

$106 total

Oct 8 - Oct 9

Total with taxes and fees

6.6/10 (328 reviews)

"Building was dated, but it was clean and tidy. Reception was pleasant. Good experience overall."

Reviewed on Jul 5, 2026

See all 690 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.