Maidstone Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • Better together

    Save up to ₩234,741 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

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

Maidstone Hotel Deals

Caesars Windsor - A Caesars Rewards Destination

Caesars Windsor - A Caesars Rewards Destination

4 out of 5
377 Riverside Dr E, Windsor, ON
The price is ₩156,421 per night from Nov 6 to Nov 7
₩156,421
₩216,404 total
Nov 6 - Nov 7
includes taxes & fees
8.6/10 Excellent! (3,092 reviews)
We love seeing a show and staying at Caesars Winds
The staff couldn’t have been more friendly, helpful, or kind!

Reviewed on Oct 26, 2025

Caesars Windsor - A Caesars Rewards Destination
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 ₩95,251 per night from Nov 2 to Nov 3
₩95,251
₩114,091 total
Nov 2 - Nov 3
includes taxes & fees
8/10 Very Good! (1,012 reviews)
Nice and convenient

Reviewed on Oct 26, 2025

Best Western Plus Waterfront Hotel
DoubleTree by Hilton Windsor Hotel & Suites

DoubleTree by Hilton Windsor Hotel & Suites

4 out of 5
333 Riverside Dr W, Windsor, ON
Fully refundableReserve now, pay when you stay
The price is ₩169,529 per night from Nov 2 to Nov 3
₩169,529
₩203,062 total
Nov 2 - Nov 3
includes taxes & fees
9/10 Wonderful! (1,030 reviews)
The breakfast unfortunately was not included in our stay it also didn’t give us the option not sure if it was due to Expedia or the hotel that was pretty much only downside, other than that stay was nice hotel seemed clean somewhat close to everything in city all in all decent stay.

Reviewed on Oct 23, 2025

DoubleTree by Hilton Windsor Hotel & Suites
See all 418 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.