Windsor Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Windsor Hotel Deals

Brydone Hotel Oamaru

Brydone Hotel Oamaru

3.5 out of 5
115 Thames Street Oamaru
$76 nightly
The price is $89 total per night from May 27 to May 28
$89 total
May 27 - May 28
Total with taxes and fees
8.6/10 Excellent! (609 reviews)
Check in was excellent. Very friendly and helpful. We were given a room upgrade. A pleasant surprise. The Bistro and dining room were great. The food was a bit pricey but we didn’t mind paying a bit more to eat in when we were looked after so well. We would stay there again.

Reviewed on Apr 28, 2026

Brydone Hotel Oamaru
Poshtel

Poshtel

5 out of 5
126 Thames Street Oamaru Otago
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $116 total per night from Jun 1 to Jun 2
$116 total
Jun 1 - Jun 2
Total with taxes and fees
9.6/10 Exceptional! (401 reviews)
Beautiful hotel, family run business that went out of their way to make us feel welcome. We had a nice continental breakfast as well. Definitely recommend staying here

Reviewed on May 7, 2026

Poshtel
The Mews Oamaru

The Mews Oamaru

4.5 out of 5
26 Exe Street Oamaru
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $104 total per night from Jun 7 to Jun 8
$104 total
Jun 7 - Jun 8
Total with taxes and fees
9.4/10 Exceptional! (361 reviews)
Great

Reviewed on Apr 29, 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.

Find the Best Windsor Vacation Packages

Windsor Essential Information

Language
English
Currency
New Zealand dollars
Max Temp Winter
50ºF
Max Temp Summer
60ºF
Top Sights
Oamaru Gardens, Janet Frame House and Totara Estate

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

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?
Usually, a handful of days is enough to go to the major attractions during your Windsor vacation. But if you'd like to have time to kick back or take day tours, think about extending your trip.
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.
Does Expedia offer Book Now, Pay Later Windsor vacation packages?
Secure your dream trip to Windsor with our Book Now, Pay Later vacations. No need to save like crazy or hold off until payday — we've partnered with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans let you spread the total cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to budget for your trip and snap up bargains before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.