Windsor Holidays

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    Save up to S$134 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Windsor

Oamaru Motor Lodge
Oamaru Motor Lodge
4 out of 5
391 Thames Highway, Oamaru
Fully refundableReserve now, pay when you stay
The price is S$123 per night from 7 Dec to 8 Dec
S$123
includes taxes & fees
7 Dec - 8 Dec
9.4/10 Exceptional! (634 reviews)
"Very nice modern apartment good location too for visiting the penguins in the evening"

Reviewed on 20 Nov,2024

Oamaru Motor Lodge
Brydone Hotel Oamaru
Brydone Hotel Oamaru
3.5 out of 5
115 Thames Street, Oamaru
The price is S$124 per night from 26 Nov to 27 Nov
S$124
includes taxes & fees
26 Nov - 27 Nov
8.4/10 Very Good! (472 reviews)
"Just a good place to stay in the middle of town. Nice friendly staff."

Reviewed on 13 Nov,2024

Brydone Hotel Oamaru
Poshtel
Poshtel
5 out of 5
126 Thames Street, Oamaru, Otago
Fully refundableReserve now, pay when you stay
The price is S$147 per night from 8 Dec to 9 Dec
S$147
includes taxes & fees
8 Dec - 9 Dec
9.4/10 Exceptional! (250 reviews)
Cute place, but too small
"Very well-decorated room in a renovated historic building on a busy road. The front desk person was very friendly and helpful. The room was small but cozy. The parking was a block away, which wasn't a problem, but there wasn't any place to drop off your luggage while you checked in. The continental ..."

Reviewed on 19 Nov,2024

Poshtel
See all 71 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?
Tailor make your Windsor holiday package from a low . Pick from any combination of rental cars, flights and hotels to craft the escape you’ve long been dreaming about. Be sure to add on one or two experiences!
How do I get a cheap travel package to Windsor?
It’s as simple as bundling. Hotels, flights and rental cars — combine whatever you need into a Windsor holiday package to save tons of cash. Score even bigger bargains when you include extras such as activities or tours to your booking. But that’s not the only impressive part. You have the flexibility to customize your holiday your way. We offer more than 550 partner airlines and 1,000,000 hotel options worldwide, so that everyone has an opportunity to travel and live out those holiday fantasies.
Where should I stay in Windsor?
An escape to Windsor wouldn’t be complete without checking out Old School Gallery. Why not book a hotel near this interesting attraction?
How far in advance should I book my Windsor holiday?
Browse Expedia to compare airfares as soon as you know your travel dates. In most cases, you can purchase a ticket up to a year before departure. If it’s too early for your preferred air carrier, or you’ve left things to the last minute, don’t stress. Cheap tickets to Windsor occasionally appear just weeks before the date of departure.
What does an Expedia Windsor travel package include?
Hotels, flights and rental cars, or any combination of them — it’s your pick! Whether you’re venturing to Windsor with the entire family or travelling with your friends, there’s a package to suit your style and budget. Once you’ve made your booking, why not add on one or two tours or activities?
Can I choose my airline with a Windsor Expedia holiday package?
You can, and with over 550 airlines to pick from across the globe, you’re not short on choice. Have a look through the available options and see which airline best fits your needs and budget.
If I'm not able to travel, can I cancel my Windsor holiday package?
It is possible to cancel your Windsor booking if your travel plans have been upended. Whether you’ll incur a fee or not depends on your hotel, airline or car rental company. It may be possible to change or cancel free of charge if you booked in the last 24 hours. Visit our Customer Service Portal for more information.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.