Windsor Holidays

Book a Hotel + Flight or Car together to unlock savings

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 2.336.745 ₫ per night from 31 Aug to 1 Sept
2.336.745 ₫
2.687.272 ₫ total
31 Aug - 1 Sept
includes taxes & fees
9.4/10 Exceptional! (316 reviews)
"This is a fabulous place to stay. So very cleverly put together. Felt safe and very welcome. Could have some background music in lobby and breakfast room. Great breakfast. Will stay again."

Reviewed on 8 Aug 2025

Poshtel
The Mews Oamaru

The Mews Oamaru

4.5 out of 5
26 Exe Street, Oamaru
The price is 2.623.445 ₫ per night from 17 Aug to 18 Aug
2.623.445 ₫
3.016.962 ₫ total
17 Aug - 18 Aug
includes taxes & fees
9.2/10 Wonderful! (346 reviews)
"The motel is very good, I think it is the best choice in Oamaru. It has spa bath, very clean and all the other details are also very good. Definitely will come back."

Reviewed on 13 Jul 2025

The Mews Oamaru
AAA Thames Court Motel

AAA Thames Court Motel

3 out of 5
252 Thames Street, Oamaru
The price is 2.069.006 ₫ per night from 20 Aug to 21 Aug
2.069.006 ₫
2.379.357 ₫ total
20 Aug - 21 Aug
includes taxes & fees
9/10 Wonderful! (223 reviews)
"Great stay, basic but everything we needed."

Reviewed on 4 Jul 2025

AAA Thames Court Motel
See all 72 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.