Maidstone Holidays

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    Better together

    Save up to €185 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

Top hotels in Maidstone

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 €111 per night from 31 Jul to 1 Aug
€111
31 Jul - 1 Aug
includes taxes & fees
8/10 Very Good! (1,038 reviews)
"Water view room is the best, you will see Freighter ships travel up and down the connecting great lakes , plus the detroit downtown vista s are còls as well"

Reviewed on 27 Jul 2025

Best Western Plus Waterfront Hotel
Caesars Windsor

Caesars Windsor

4 out of 5
377 Riverside Dr E, Windsor, ON
The price is €135 per night from 17 Aug to 18 Aug
€135
17 Aug - 18 Aug
includes taxes & fees
8.4/10 Very Good! (3,055 reviews)
"I enjoyed my stay here. The keycards were a little difficult at times to use for many people. It became a joke for everyone who used the elevators in the Forum tower because it would not always scan properly. I also look young for my age, so I made sure I walk with my ID because I was stopped upon ..."

Reviewed on 28 Jul 2025

Caesars Windsor
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 €123 per night from 3 Aug to 4 Aug
€123
3 Aug - 4 Aug
includes taxes & fees
8.8/10 Excellent! (1,014 reviews)
"Great experience"

Reviewed on 26 Jul 2025

DoubleTree by Hilton Windsor Hotel & Suites
See all 415 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 holiday 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 holiday 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 holiday?
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 favourite 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 holiday.
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 holiday package?
Yes — that's the beauty of an Expedia holiday 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 holiday 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.