Maidstone Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Maidstone

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 2.724.965 ₫ per night from 8 Mar to 9 Mar
2.724.965 ₫
3.801.911 ₫ total
8 Mar - 9 Mar
includes taxes & fees
8.6/10 Excellent! (3,205 reviews)
Would stay again

Reviewed on 15 Feb 2026

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 1.965.174 ₫ per night from 22 Feb to 23 Feb
1.965.174 ₫
2.353.829 ₫ total
22 Feb - 23 Feb
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
Staff was amazing, location is perfect. The hotel is clean and decently maintained. But number 1, your staff are incredible. From the restaurant to the desk to the house keeping. All are so polite and professional.

Reviewed on 15 Feb 2026

Best Western Plus Waterfront Hotel
Holiday Inn Express Windsor Waterfront by IHG

Holiday Inn Express Windsor Waterfront by IHG

2.5 out of 5
33 Riverside Drive East Windsor ON
Fully refundable
The price is 2.726.869 ₫ per night from 25 Feb to 26 Feb
2.726.869 ₫
3.266.243 ₫ total
25 Feb - 26 Feb
includes taxes & fees
8.6/10 Excellent! (1,380 reviews)
Very clean, clean and modern building

Reviewed on 8 Feb 2026

Holiday Inn Express Windsor Waterfront by IHG
See all 426 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 great live music.

Ciocairo Club of Windsor