Maidstone Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to ￥45,448 when you book a flight and hotel together*
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    Find the right fit

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

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

Maidstone Hotel Deals

Caesars Windsor

Caesars Windsor

4 out of 5
377 Riverside Dr E, Windsor, ON
The price is ￥16,323 per night from Oct 6 to Oct 7
￥16,323
￥22,582 total
Oct 6 - Oct 7
includes taxes & fees
8.6/10 Excellent! (3,088 reviews)
Wonderful stay!
"Stay was great. The casino is so clean and beautiful. Loved it!!"

Reviewed on Sep 24, 2025

Caesars Windsor
Best Western Plus Waterfront Hotel

Best Western Plus Waterfront Hotel

2.5 out of 5
277 Riverside Drive West, Windsor, ON
Fully refundableReserve now, pay when you stay
The price is ￥14,499 per night from Oct 1 to Oct 2
￥14,499
￥17,366 total
Oct 1 - Oct 2
includes taxes & fees
8/10 Very Good! (1,002 reviews)
"Everything"

Reviewed on Sep 25, 2025

Best Western Plus Waterfront Hotel
Holiday Inn Express Windsor Waterfront by IHG

Holiday Inn Express Windsor Waterfront by IHG

2.5 out of 5
33 Riverside Drive East, Windsor, ON
Fully refundable
The price is ￥16,736 per night from Oct 1 to Oct 2
￥16,736
￥20,048 total
Oct 1 - Oct 2
includes taxes & fees
8.6/10 Excellent! (1,340 reviews)
"The room was a bit small and they had the tv infront of one bed only and a dresser right beside it so you couldn’t really see the tv from the other bed. Staff were great, beds comfy, pillows nice, view of city was good, the area was cute right by the water and a walking area to go sit and look at ..."

Reviewed on Sep 28, 2025

Holiday Inn Express Windsor Waterfront by IHG
See all 428 properties in Maidstone
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 Maidstone vacation package cost?
Starting from as low as , you can create your own Maidstone package. Simply combine flights, hotels and car rentals and we'll reward you with discounts.
How do I get a cheap travel package to Maidstone?
Booking a Maidstone vacation package with Expedia is a smart way to save. We have access to more than 550 partner airlines and 1,000,000 hotel options across the globe. With such an awesome range to pick from, you'll have no issues putting together your dream escape.
How far in advance should I book my Maidstone vacation?
While not all airlines release tickets early, it's usually possible to look up international flights on Expedia up to 12 months in advance. This is the time when you'll nab some fantastic deals. If you're booking last minute, there's a chance you could get lucky. Sometimes the lowest prices emerge a few weeks before departure.
What does an Expedia Maidstone travel package include?
Flights, car rentals and hotels — we bring you the very best bargains. All you have to do is pick your favorite combination. After you've made your booking, you can add on the exciting stuff like experiences and tours. Our travel packages make it simple to create an awesome Maidstone vacation.
What should I know before booking a Maidstone travel package?
You can save big by combining your flights, hotels and rental cars. Once you've created your package, you can add on sightseeing tours or experiences. Your next awesome adventure is only a few clicks away.
Can I choose my airline with a Maidstone Expedia vacation package?
Yes — that's the beauty of an Expedia vacation package. You get to decide. We have access to more than 550 airline partners throughout the world, so you have options galore when planning your Maidstone adventure.
If I'm not able to travel, can I cancel my Maidstone vacation package?
You can cancel your Maidstone booking if your travel plans have changed. Whether you'll incur a fee or not depends on your hotel, airline or car rental company. You may be able to cancel or change free of charge if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.