Windsor Vacations from $1,232

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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 Harbour Suites

YEHS Hotel Sydney Harbour Suites

4 out of 5
Sydney Central Business District
Price was $1,576, price is now $1,232 per person
$1,232
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Sydney (SYD)
8.2/10 Very Good! (2,770 reviews)
Great Location...near Pitt Street Mall...Darling Harbour...fantastic for Vivid Festival..stayed in a suite bedroom..so kitchen facilities..and lounge area.. Cafe next door for breakfast..good value..

Reviewed on Jun 11, 2026

Nesuto Woolloomooloo Sydney Apartments

Nesuto Woolloomooloo Sydney Apartments

3.5 out of 5
Woolloomooloo
Price was $1,750, price is now $1,577 per person
$1,577
per person
Jul 26 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Sydney (SYD)
8.6/10 Excellent! (1,000 reviews)
Enjoyed our stay, clean, had everything we needed.

Reviewed on May 23, 2026

Bright 2-bed Flat With Balcony in Vaucluse

Bright 2-bed Flat With Balcony in Vaucluse

2.5 out of 5
Vaucluse
Price was $3,016, price is now $2,396 per person
$2,396
per person
Aug 26 - Aug 31
found 18 hours ago
Roundtrip flight included
Los Angeles (LAX) to Sydney (SYD)
No reviews
Sofitel Sydney Darling Harbour

Sofitel Sydney Darling Harbour

5 out of 5
Sydney Central Business District
Price was $3,335, price is now $2,698 per person
$2,698
per person
Aug 26 - Aug 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sydney (SYD)
9/10 Wonderful! (1,010 reviews)
My first 5 star hotel experience, I can understand why people pay the extra

Reviewed on Jun 11, 2026

Spicers Potts Point

Spicers Potts Point

4.5 out of 5
Potts Point
Price was $3,651, price is now $2,962 per person
$2,962
per person
Aug 26 - Aug 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sydney (SYD)
9.8/10 Exceptional! (154 reviews)
Potts Point is a great area to base yourselves in in Sydney and Spicers is a great "hotel" - actually, that's too impersonal, it feels more like a home away from home. The reception staff are interested and attentive, our room (No.8) was well provisioned and superclean, we were in walking distance of interesting local shops and restaurants, and a short Uber to the CBD. Thoroughly recommend.

Reviewed on Apr 25, 2026

Where to stay in Windsor

Find the best Windsor areas and neighborhoods for the activities you enjoy most. Learn more about Windsor
Three horses in the shade in a field on the Great Northern Road between Wiseman's Ferry and Bucketty, Yengo National Park, NSW, Australia

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.

Find hotels in Wisemans Ferry

Windsor Hotel Deals

Crowne Plaza Hawkesbury Valley by IHG

Crowne Plaza Hawkesbury Valley by IHG

4 out of 5
61 Hawkesbury Valley Way Windsor NSW
Fully refundable
$114 nightly
The price is $126 total per night from Jun 21 to Jun 22
$126 total
Jun 21 - Jun 22
Total with taxes and fees
9/10 Wonderful! (1,004 reviews)
"Very nice room and great breakfast. Only downside was no microwave in the room we stayed in."

Reviewed on Jun 8, 2026

Crowne Plaza Hawkesbury Valley by IHG
Windsor Heritage Motel

Windsor Heritage Motel

3 out of 5
54 George Street Windsor NSW
$69 nightly
The price is $77 total per night from Jun 13 to Jun 14
$77 total
Jun 13 - Jun 14
Total with taxes and fees
5.2/10 (301 reviews)
"Permanent residents noisy"

Reviewed on May 31, 2026

Windsor Heritage Motel
Windsor Riverview Inn

Windsor Riverview Inn

3 out of 5
47 George Street Windsor NSW
$92 nightly
The price is $102 total per night from Jul 13 to Jul 14
$102 total
Jul 13 - Jul 14
Total with taxes and fees
6.6/10 (327 reviews)
"Room was clean. Tv worked but could only access Network 10 channels only. Very disappointing."

Reviewed on May 3, 2026

Windsor Riverview Inn
See all 678 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
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Stay near popular Windsor attractions

Hawkesbury Regional Gallery

Hawkesbury Regional Gallery is just one of the places to see in Sydney, so why not enjoy the other things to explore during your travels? Amble within the gardens or visit the spas in this relaxing area.
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