Maidstone Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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 S$183 per night from 4 May to 5 May
S$183
4 May - 5 May
includes taxes & fees
8.6/10 Excellent! (3,206 reviews)
It would of been great if I know how to pick a room on the river. Perhaps your website should tell you the the view is we tried to get a room facing the river but they refuse because we went through your website

Reviewed on 29 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 S$149 per night from 10 May to 11 May
S$149
10 May - 11 May
includes taxes & fees
9.2/10 Wonderful! (1,077 reviews)
Our family of four stayed at this hotel and, on the surface, it was ok and appeared clean and in good working order. Both beds in our room were broken, both sides of the beds being raised creating a V shape and making it very difficult to rest comfortably. The bathroom had black mold on the floor, ...

Reviewed on 28 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 S$100 per night from 21 May to 22 May
S$100
21 May - 22 May
includes taxes & fees
8/10 Very Good! (1,277 reviews)
All good

Reviewed on 29 Apr, 2026

Comfort Inn & Suites Ambassador Bridge
See all 433 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.