Maidstone Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

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

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

Your Maidstone Vacation

Say goodbye to the hassle of planning and hello to a Maidstone vacation package. With the finer details organized before you take off, you can focus on discovering this city, starting with Greektown Historic District, which is good for history, dining and culture. Your trip to Maidstone wouldn't be complete without visiting its top attractions, such as McAuliffe Woods Conservation Area Trail Trailhead. A couple of clicks is all it takes to build a customized Maidstone vacation on Expedia.

Top Holiday Package Deals in Maidstone

Price found within the past 48 hours. Click for updated prices.
Nicklin House
Windsor Manor
Parkside Flat #5 - Seacliff Beach Suites
Travelodge by Wyndham Windsor
Holiday Inn Express & Suites Windsor East - Lakeshore by IHG

Maidstone Hotel Deals

Caesars Windsor

Caesars Windsor

4 out of 5
377 Riverside Dr E, Windsor, ON
The price is CA $152 per night from Sep 1 to Sep 2
CA $152
CA $207 total
Sep 1 - Sep 2
includes taxes & fees
Caesars Windsor
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 CA $144 per night from Sep 7 to Sep 8
CA $144
CA $172 total
Sep 7 - Sep 8
includes taxes & fees
Holiday Inn Express Windsor Waterfront by IHG
Holiday Inn & Suites Windsor Ambassador Bridge by IHG

Holiday Inn & Suites Windsor Ambassador Bridge by IHG

3.5 out of 5
1855 Huron Church Road, Windsor, ON
Fully refundable
The price is CA $161 per night from Sep 4 to Sep 5
CA $161
CA $199 total
Sep 4 - Sep 5
includes taxes & fees
7.4/10 Good! (1,013 reviews)
"Overall our stay was good. The bed was so very comfortable. The dressers are worn and older and we did not get coffee cups in our room."

Reviewed on Aug. 24, 2025

Holiday Inn & Suites Windsor Ambassador Bridge by IHG
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 vacation package cost?
Starting from as low as CA $763, 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 vacation 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 vacation?
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 favorite 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 vacation.
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 vacation package?
Yes — that's the beauty of an Expedia vacation 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 vacation 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.