Maidstone Holidays

Book a Hotel + Flight or Car together to unlock savings

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 1.769.782 ₫ per night from 4 Jan to 5 Jan
1.769.782 ₫
2.119.845 ₫ total
4 Jan - 5 Jan 2026
includes taxes & fees
8/10 Very Good! (1,004 reviews)
Easy parking on a cold day. Staff is great. Keg next door. Was just great

Reviewed on 10 Dec 2025

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 2.906.339 ₫ per night from 15 Dec to 16 Dec
2.906.339 ₫
4.020.838 ₫ total
15 Dec - 16 Dec
includes taxes & fees
8.6/10 Excellent! (3,160 reviews)
Very clean room, staff very helpfull

Reviewed on 9 Dec 2025

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 3.038.714 ₫ per night from 4 Jan to 5 Jan
3.038.714 ₫
3.639.771 ₫ total
4 Jan - 5 Jan 2026
includes taxes & fees
9/10 Wonderful! (1,044 reviews)
Clean room…friendly staff…prompt response from housekeeping

Reviewed on 12 Dec 2025

DoubleTree by Hilton Windsor Hotel & Suites
See all 424 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 1null000null000 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.

Popular places to visit

Ciocairo Club of Windsor

Why not roll the dice with a visit to Ciocairo Club of Windsor during your visit to Tecumseh? Amble around this vibrant area's riverfront or experience its acclaimed theatre scene.

Ciocairo Club of Windsor