Maidstone Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

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

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

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    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.
Towneplace Suites By Marriott Tecumseh Windsor

Towneplace Suites By Marriott Tecumseh Windsor

2 out of 5
Price was CA $1,023, price is now CA $890 per person
CA $890
per person
May 28 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Comox (YQQ) to Windsor (YQG)
9.6/10 Exceptional! (41 reviews)
This is a nice, new hotel. I hope they can keep it up in terms of cleanliness and freshness, because we had a great stay and will stay here again in the future as long as it’s the same experience. Room is well equipped, with comfortable beds, linens and pillows. Tyler at the bar was great and made a good cocktail. I love to see a hotel like this with a bar. Very reasonable prices.

Reviewed on Mar 9, 2026

Holiday Inn Express & Suites Windsor East - Lakeshore by IHG

Holiday Inn Express & Suites Windsor East - Lakeshore by IHG

2.5 out of 5
Price was CA $991, price is now CA $908 per person
CA $908
per person
May 28 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Comox (YQQ) to Windsor (YQG)
9.4/10 Exceptional! (1,002 reviews)
Breakfast was good. The people were friendly. Lot was well lit with multiple entry points, so you're not required to walk around the building at night to get in.

Reviewed on Apr 9, 2026

Maidstone Hotel Deals

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 CA $127 per night from May 11 to May 12
CA $127
CA $177 total
May 11 - May 12
includes taxes & fees
8.6/10 Excellent! (3,183 reviews)
I went to the front desk at 6am to check out but said I wouldn’t be leaving the room until 7:30am. I paid up and the one at the front desk said she didn’t che k me out so that my key would work, well as soon as my door shut and I was heading to the elevator with no key, I knew I was in trouble. I ...

Reviewed on Apr 10, 2026

Caesars Windsor - A Caesars Rewards Destination
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 $139 per night from May 10 to May 11
CA $139
CA $166 total
May 10 - May 11
includes taxes & fees
8.6/10 Excellent! (1,365 reviews)
The breakfast was excellent. I won't be back at this location because of the parking. Should not be first come first served. I came in late as this was a business stay. I couldn't get parking near the hotel and was advised to go to the underground parking. It's too bad as I'm in Windsor 3 times ...

Reviewed on Apr 10, 2026

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 $105 per night from Apr 19 to Apr 20
CA $105
CA $130 total
Apr 19 - Apr 20
includes taxes & fees
Holiday Inn & Suites Windsor Ambassador Bridge by IHG
See all 429 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 Vacations
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Frequently asked questions

How much does a Maidstone vacation package cost?
Starting from as low as CA $890, 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.