Windsor Vacation Packages 2026 from $1,450

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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 QVB

Sydney Central Business District

$1,450

per person

Nov 8 - Nov 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sydney (SYD)

8.6/10 Excellent! (1,008 reviews)

Room was a good size, clean and comfortable. Its not luxury accommodation, but its certainly not a dump and more that satisfied us for 3 days in central Sydney. Brilliant location next to the QVC. If you want somewhere safe, clean and comfortable and don't require 5 star luxury then this is the place. I would happily stay here again.

Reviewed on Sep 4, 2026

Kith Hotel Darling Harbour

Pyrmont

$1,484

per person

Nov 24 - Nov 28

found 1 day ago

Roundtrip non-stop flight included

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

8.8/10 Excellent! (513 reviews)

Very convenient, clean and close to light rail and Darling Harbour. Room a little small but ideal for a single person or couple. Will definitely stay there again as easy access to the Fish Markets and inner west.

Reviewed on Sep 4, 2026

YEHS Hotel Sydney Harbour Suites

Sydney Central Business District

$1,699

per person

Oct 15 - Oct 18

just found

Roundtrip non-stop flight included

New York (JFK) to Sydney (SYD)

8.2/10 Very Good! (2,903 reviews)

Hotel was conveniently located in the heart of

Reviewed on Sep 4, 2026

Elysium Manly

Manly

$1,930

per person

Nov 8 - Nov 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sydney (SYD)

9/10 Wonderful! (379 reviews)

This property was lovely and directly across from the beach. The staff were excellent, meals were fantastic and it was centrally located and walkable to shopping and enjoying the seaside board walk.

Reviewed on Aug 30, 2026

Capella Sydney

Sydney Central Business District

$2,879

per person

Oct 19 - Oct 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sydney (SYD)

9.8/10 Exceptional! (410 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.

Berowra Waters

While visiting Berowra Waters, you might make a stop by sights like Berowra Waters Marina and Marramarra National Park.

A boat on a sandy beach, a calm lake, and hills in the background.

Dangar Island

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

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

$124 nightly

$137 total

Sep 27 - Sep 28

Total with taxes and fees

9/10 Wonderful! (1,000 reviews)

"Like: - Beautiful area for the breakfast buffet and great selection of food! - We booked the king room for 2 adults and 1 child 10 yrs old. They put in an extra bed w/o being asked. - Indoor heated pool n spa were great but the pool is tiny and can get pretty busy. - Microwave in room - Gave free ..."

Reviewed on Aug 19, 2026

Windsor Heritage Motel

54 George Street Windsor NSW

$74 nightly

$82 total

Sep 6 - Sep 7

Total with taxes and fees

5.2/10 (308 reviews)

"It was what one expected for the price. A little dusting within room required but overall good."

Reviewed on Aug 31, 2026

Rydges Parramatta

116 James Ruse Drive Rosehill NSW

Fully refundableReserve now, pay when you stay

$104 nightly

$115 total

Sep 20 - Sep 21

Total with taxes and fees

8.2/10 Very Good! (1,002 reviews)

"All ok"

Reviewed on Aug 29, 2026

See all 689 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.