Windsor Vacations

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Windsor Hotel Deals

289 Midway Motel

289 Midway Motel

3 out of 5
289 Thames Street, Oamaru
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $88 total per night from Oct 27 to Oct 28
$88 total
Oct 27 - Oct 28
Total with taxes and fees
8/10 Very Good! (299 reviews)
"They were very accommodating, meeting my request for a single bed added if it could fit (for a child). We also couldn’t make it before checkin closed and they assisted with that too. Our room had been renovated and made for a lovely comfortable stay. Thank you"

Reviewed on Sep 21, 2025

289 Midway Motel
Poshtel

Poshtel

5 out of 5
126 Thames Street, Oamaru, Otago
$90 nightly
The price is $105 total per night from Oct 14 to Oct 15
$105 total
Oct 14 - Oct 15
Total with taxes and fees
9.4/10 Exceptional! (320 reviews)
"Central, lovely staff, great breakfast. Quirky style. Would definitely recommend"

Reviewed on Sep 24, 2025

Poshtel
Oamaru Motor Lodge

Oamaru Motor Lodge

4 out of 5
391 Thames Highway, Oamaru
Fully refundableReserve now, pay when you stay
$68 nightly
The price is $79 total per night from Sep 28 to Sep 29
$79 total
Sep 28 - Sep 29
Total with taxes and fees
9.4/10 Exceptional! (688 reviews)
"Just an amazing experience"

Reviewed on Sep 13, 2025

Oamaru Motor 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.

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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.