Maidstone Holidays

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Your Maidstone Holiday

With plenty of highlights as well as some hidden gems, this city is best explored with a Maidstone holiday package. Find a place to stay in Greektown Historic District, which is good for history, dining and culture. If seeing the sights is on your list of things to do during your trip to Maidstone, schedule a stop at major attractions like McAuliffe Woods Conservation Area Trail Trailhead. Don't delay your visit to this destination any longer. The perfect Maidstone holiday is a few clicks away with Expedia.

Our pick of the best Maidstone Hotel Deals

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 AU$120 per night from 25 Jan to 26 Jan
AU$120
25 Jan - 26 Jan
includes taxes & fees
8/10 Very Good! (1,000 reviews)
Very nice place.

Reviewed on 11 Jan 2026

Best Western Plus Waterfront Hotel
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 AU$261 per night from 18 Jan to 19 Jan
AU$261
18 Jan - 19 Jan
includes taxes & fees
8.6/10 Excellent! (3,198 reviews)
The lady at the check in was terrific i received a corner room thank you

Reviewed on 12 Jan 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 AU$205 per night from 8 Feb to 9 Feb
AU$205
8 Feb - 9 Feb
includes taxes & fees
9/10 Wonderful! (1,063 reviews)
Staff very helpful and informative

Reviewed on 9 Jan 2026

DoubleTree by Hilton Windsor Hotel & Suites
See all 423 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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.