Maidstone Holidays

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Our pick of the best 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 NZ$256 per night from 24 May to 25 May
NZ$256
24 May - 25 May
includes taxes & fees
8.6/10 Excellent! (3,206 reviews)
With hotel and casino being large, took a bit to find lobby after parking but had lots of signage. Enjoyed the experience ..great food and entertainment. Hotel room was very nice. Elevators nice with outside view and very quick.

Reviewed on 25 Apr 2026

Caesars Windsor - A Caesars Rewards Destination
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 NZ$184 per night from 10 May to 11 May
NZ$184
10 May - 11 May
includes taxes & fees
9.2/10 Wonderful! (1,080 reviews)
We always stay here when we come to Windsor. We have eaten at the Riverside restaurant several times for dinner and breakfast and the food is excellent as usual and priced well. The staff at the restaurant and front desk are friendly and helpful. The hotel and restaurant are clean and well maintained. ...

Reviewed on 24 Apr 2026

DoubleTree by Hilton Windsor Hotel & Suites
Comfort Inn & Suites Ambassador Bridge

Comfort Inn & Suites Ambassador Bridge

2.5 out of 5
2330 Huron Church Rd Windsor ON
Fully refundable
The price is NZ$143 per night from 17 May to 18 May
NZ$143
17 May - 18 May
includes taxes & fees
8/10 Very Good! (1,265 reviews)
Great stay and great staff!

Reviewed on 22 Apr 2026

Comfort Inn & Suites Ambassador Bridge
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 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.