Windsor Holidays from NZ$1,390

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Top Holiday Package Deals in Windsor

Price found within the past 48 hours. Click for updated prices.
YEHS Hotel Sydney CBD

YEHS Hotel Sydney CBD

3.5 out of 5
Sydney Central Business District
Save 100% on your flight
Price was NZ$2,552, price is now NZ$1,390 per person
NZ$1,390
per person
22 May - 29 May
found 19 hours ago
Return flight included
Auckland (AKL) to Sydney (SYD)
8.2/10 Very Good! (1,001 reviews)
Very small rooms but otherwise very good

Reviewed on 29 Mar 2026

Stylish 2-bed Cottage in Trendy Erskineville

Stylish 2-bed Cottage in Trendy Erskineville

2.5 out of 5
Erskineville
Save 100% on your flight
Price was NZ$3,217, price is now NZ$1,952 per person
NZ$1,952
per person
9 May - 16 May
found 6 hours ago
Return flight included
Auckland (AKL) to Sydney (SYD)
No reviews
Spacious 3-bed With Alfresco Dining by Amenities

Spacious 3-bed With Alfresco Dining by Amenities

2 out of 5
Kingsford
Save 100% on your flight
Price was NZ$3,708, price is now NZ$2,267 per person
NZ$2,267
per person
22 May - 29 May
found 19 hours ago
Return flight included
Auckland (AKL) to Sydney (SYD)
No reviews
Spacious Stay Near Shops & Cafes in Marrickville

Spacious Stay Near Shops & Cafes in Marrickville

2.5 out of 5
Marrickville
Save 100% on your flight
Price was NZ$3,045, price is now NZ$1,874 per person
NZ$1,874
per person
9 May - 16 May
found 6 hours ago
Return flight included
Auckland (AKL) to Sydney (SYD)
No reviews
Stylish 2-bed House With Private Courtyard

Stylish 2-bed House With Private Courtyard

2.5 out of 5
Redfern
Save 100% on your flight
Price was NZ$3,543, price is now NZ$2,189 per person
NZ$2,189
per person
22 May - 29 May
found 19 hours ago
Return flight included
Auckland (AKL) to Sydney (SYD)
No reviews

Our guide on where to stay in Windsor

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

Berowra Waters

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

Find hotels in Berowra Waters

Our pick of the best 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
The price is NZ$229 per night from 15 Apr to 16 Apr
NZ$229
15 Apr - 16 Apr
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
Everything I needed in one place

Reviewed on 25 Mar 2026

Crowne Plaza Hawkesbury Valley by IHG
Windsor Heritage Motel

Windsor Heritage Motel

3 out of 5
54 George Street Windsor NSW
The price is NZ$147 per night from 8 Apr to 9 Apr
NZ$147
8 Apr - 9 Apr
includes taxes & fees
5.2/10 (299 reviews)
Room sme

Reviewed on 23 Mar 2026

Windsor Heritage Motel
Windsor Riverview Inn

Windsor Riverview Inn

3 out of 5
47 George Street Windsor NSW
The price is NZ$173 per night from 1 May to 2 May
NZ$173
1 May - 2 May
includes taxes & fees
6.6/10 (324 reviews)
The room was very clean and comfortable. However, there was no toaster or crockery despite having a microwave, and the balcony door could barely be opened.

Reviewed on 27 Nov 2025

Windsor Riverview Inn
See all 649 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.

Frequently asked questions

How much does a Windsor holiday package cost?
Perhaps less than you might think — from a tempting NZ$1,390, in fact! By combining flights, hotels and car rentals into a custom-built travel package, your Windsor escape is just clicks away.
How do I get a cheap travel package to Windsor?
If you love getting an amazing deal, combine your bookings into a Windsor holiday package. Whether you're looking for flights, hotels, rental cars or activities, you can book them all in one place. You'll have loads of choice at your fingertips too. Expedia has over 550 air carriers and 1 000 000 hotel options globally to choose from. Fly with who you want, check in where you like and save some cash — now that's the perfect getaway!
Where should I stay in Windsor?
A trip to Windsor isn't complete without visiting Hawkesbury River, Hawkesbury Race Club and Lynwood Country Club. Spend your evenings close to these attractions and make sightseeing a breeze.
What are the top hotels in Windsor?
If it's your first visit to Windsor, lock in a room at Crowne Plaza Hawkesbury Valley, an IHG Hotel or Windsor Terrace Motel. Both will make you feel at home and are favourites with lots of travellers.
How far in advance should I book my Windsor holiday?
Reserving your flights early with Expedia means one less thing to have to worry about. Most air carriers advertise tickets up to a year in advance. This is usually the cheapest time to book. If circumstances have left you booking late, low prices to Windsor will sometimes occur in the weeks leading up to departure.
What does an Expedia Windsor travel package include?
Expedia has all you need to book your Windsor escape, but what your package looks like depends on you. Choose from a combination of rental cars, flights and hotels. After some tours or experiences to fill in your time? Once you've made your booking, you can add them on too. No matter your budget or style, there's a package to suit your needs.
What should I know before booking a Windsor travel package?
A travel package can be customized for your circumstances and is a fantastic way to stretch your hard-earned dollars. What you include is completely up to you. Rental cars, hotels and flights — come up with a combination that works with your plans.
Can I choose my airline with a Windsor Expedia holiday package?
Expedia has access to more than 550 airline partners globally, so you sure can! Just select your favourite carrier and put together your ideal Windsor trip.
If I'm not able to travel, can I cancel my Windsor holiday package?
It's impossible to predict what the future holds, so it's comforting to know that you can cancel or change your Windsor holiday package. If you booked in the last 24 hours, you may be eligible for a refund. If your booking is older, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal for more information.

Discover the most popular places to visit in Windsor

Sydney Opera House

Sydney Opera House

4.5/5(3,528 reviews)

The bold lines of the Sydney Opera House speak more about Sydney than any other part of this cosmopolitan city of four million.

Sydney Opera House
Circular Quay

Circular Quay

4.5/5(4,928 reviews)

Trains, buses and boats all make a bee-line for Circular Quay, a place at the heart of Sydney's journeying – and so should you.

Circular Quay
Sydney Harbour Bridge

Sydney Harbour Bridge

4.5/5(3,629 reviews)

A colossus of engineering, the Harbour Bridge brings the pieces of Sydney together, and offers you a different perspective on the city's wide-angle drama.

Sydney Harbour Bridge

Activities

Sydney Hop-On Hop-Off Big Bus Tour

Big Bus Sydney Hop-On Hop-Off Sightseeing Tour by Open-Top Bus

NZ$74
per adult
86% of travellers recommend
Big Bus Sydney Hop-On Hop-Off Sightseeing Tour by Open-Top Bus
Sydney Attractions Pass including SEA LIFE Sydney Aquarium

Sydney Attractions Pass including SEA LIFE Sydney Aquarium

NZ$61
per adult
86% of travellers recommend
Sydney Attractions Pass including SEA LIFE Sydney Aquarium
BridgeClimb Summit at Sydney Harbour Bridge

BridgeClimb Summit at Sydney Harbour Bridge

NZ$401
per adult
98% of travellers recommend
BridgeClimb Summit at Sydney Harbour Bridge
See all activities in Sydney
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.