Windsor Trips (flight + hotel)

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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 P5,419 per night from Jul 13 to Jul 14
P5,419
P6,232 total
Jul 13 - Jul 14
includes taxes & fees
9.4/10 Exceptional! (304 reviews)
"A bit of a hidden gem, close to the centre, lovely stay"

Reviewed on Jun 24, 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 P5,037 per night from Jun 28 to Jun 29
P5,037
P5,793 total
Jun 28 - Jun 29
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 May 26, 2025

Oamaru Motor Lodge
Heritage Court Lodge
Heritage Court Lodge
4 out of 5
346 Thames Highway, Oamaru
Fully refundableReserve now, pay when you stay
8.4/10 Very Good! (361 reviews)
"Really handy to the town and shopping and cafes. Unfortunately the unit was cold on arrival...no heating turned on and extremely cold day. Unit was very clean and tidy. There was a locked door to the next unit and you could hear all conversation."

Reviewed on Jun 22, 2025

Get rates
Heritage Court Lodge
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 vacation package cost?
You can pick up a vacation package to this destination on Expedia. However, how much your vacation 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 vacation 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-organized 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 vacation 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 personalize 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 vacation as a package?
You can enjoy significant savings on your Windsor retreat by booking a customized vacation 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 vacation 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, favorite 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 accommodations 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 customized Windsor vacation package.

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