Windsor Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to NZ$616 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Windsor Holiday

Our pick of the best Windsor Hotel Deals

Poshtel
Poshtel
5 out of 5
126 Thames Street, Oamaru, Otago
Fully refundableReserve now, pay when you stay
The price is NZ$182 per night from 25 June to 26 June
NZ$182
25 June - 26 June
includes taxes & fees
9.4/10 Exceptional! (301 reviews)
"We love Poshtel! From our arrival to our departure, everything was wonderful. The staff is incredibly kind and offered a wealth of information. Each room in the hotel is uniquely decorated. There are a lot of shopping and dining options within walking distance."

Reviewed on 18 Jun. 2025

Poshtel
Oamaru Motor Lodge
Oamaru Motor Lodge
4 out of 5
391 Thames Highway, Oamaru
Fully refundableReserve now, pay when you stay
The price is NZ$165 per night from 8 July to 9 July
NZ$165
8 July - 9 July
includes taxes & fees
9.4/10 Exceptional! (674 reviews)
Good motel
"Condition of room was very good. Very warm and quiet. Small kitchenette. Average size bathroom with good shower water pressure (although ran out of hot water one morning). Bed was a little too soft and bouncy for our liking"

Reviewed on 26 May 2025

Oamaru Motor Lodge
Brydone Hotel Oamaru
Brydone Hotel Oamaru
3.5 out of 5
115 Thames Street, Oamaru
The price is NZ$156 per night from 16 July to 17 July
NZ$156
16 July - 17 July
includes taxes & fees
8.4/10 Very Good! (529 reviews)
"Good overall"

Reviewed on 27 May 2025

Brydone Hotel Oamaru
See all 73 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?
You can pick up a holiday package to this destination on Expedia. However, how much your holiday to Windsor costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Windsor?
February, November and December are the best times to look for cheap Windsor holiday packages. Opting to travel in less busy periods means you can generally find lower prices on hotels and flights.
How many days is enough for Windsor?
With a well-organised itinerary, you can easily visit the most popular Windsor attractions in a handful of days. But if you want to explore off the beaten track or take day trips, think about booking your Windsor holiday for longer.
How to find the best Windsor package deals?
Landing a cheap Windsor package deal is a breeze with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, add a few filters and browse what's available. You can personalise your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Windsor package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Windsor holiday as a package?
You can enjoy significant savings on your Windsor retreat by booking a customised holiday package. Check the "Package" heading, then enter your destination and travel dates to browse some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Windsor?
If you've got your Windsor travel dates finalized, book as soon as you can to grab some unbeatable deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Windsor?

  1. Pick the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to go to Windsor.
  2. Work out your budget: Make sure you have enough money to cover everything from transportation and dining out to flights and activities. Your accommodation will probably be the biggest expense during your trip to Windsor.
  3. Decide how long to go away for: Now that you know more about Windsor, you can figure out the perfect length of your break. Put together a draft itinerary and allocate enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a customised Windsor holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.