Windsor Holidays

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Top hotels in Windsor

Poshtel

Poshtel

5 out of 5
126 Thames Street Oamaru Otago
Fully refundableReserve now, pay when you stay
The price is S$130 per night from 30 Jul to 31 Jul
S$130
30 Jul - 31 Jul
includes taxes & fees
9.6/10 Exceptional! (416 reviews)
"I absolutely loved this accommodation, and it was much better than expected :). Looking forward to next time already."

Reviewed on 15 Jun, 2026

Poshtel
Brydone Hotel Oamaru

Brydone Hotel Oamaru

3.5 out of 5
115 Thames Street Oamaru
The price is S$114 per night from 8 Aug to 9 Aug
S$114
8 Aug - 9 Aug
includes taxes & fees
8.6/10 Excellent! (629 reviews)
"Great location"

Reviewed on 12 Jul, 2026

Brydone Hotel Oamaru
The Mews Oamaru

The Mews Oamaru

4.5 out of 5
26 Exe Street Oamaru
The price is S$141 per night from 26 Jul to 27 Jul
S$141
26 Jul - 27 Jul
includes taxes & fees
9.4/10 Exceptional! (367 reviews)
"Everything was there that we needed. Lovely & warm on arrival which was great. Easy parking & nothing was far away."

Reviewed on 7 Jul, 2026

The Mews Oamaru
See all 74 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.

Explore a world of travel with Expedia

* 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.