Maidstone Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $4,200 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

2.5 out of 5
Price was CA $1,053, price is now CA $992 per person
CA $992
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Windsor (YQG)
9.6/10 Exceptional! (179 reviews)

Hotel STRY

Hotel STRY

2 out of 5
Price was CA $1,263, price is now CA $1,116 per person
CA $1,116
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Windsor (YQG)
10/10 Exceptional! (46 reviews)
A unique, beautiful, clean and well-maintained place to stay. The room was incredible and the owner Laurie was so helpful at checkin. I can’t say more about the decor and themed rooms! We will definitely stay again.

Reviewed on Oct 27, 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 $1,092, price is now CA $1,027 per person
CA $1,027
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Windsor (YQG)
9.6/10 Exceptional! (1,010 reviews)
I have picked the hotel because, indoor pool, free parking and location near a plaza.

Reviewed on Oct 27, 2026

Days Inn by Wyndham Leamington

Days Inn by Wyndham Leamington

2.5 out of 5
Price was CA $1,051, price is now CA $1,010 per person
CA $1,010
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Windsor (YQG)
7.8/10 Good! (1,001 reviews)
Hotel is dated but the rooms are good. Shower has lots of pressure and hot water. Room was clean but I did find a couple hairs in the bathroom and in the bed.

Reviewed on Oct 22, 2026

Dream Estate Inn

Dream Estate Inn

3.5 out of 5
Price was CA $1,054, price is now CA $1,019 per person
CA $1,019
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Windsor (YQG)
9.4/10 Exceptional! (138 reviews)
Turn in to property driveway is awkward when approaching from WB Seacliffe and borderline unsafe when coming EB from the roundabout. Remember- Leamington drivers can often be unpredictable.

Reviewed on Oct 19, 2026

Maidstone Hotel Deals

Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

4 out of 5
377 Riverside Dr E Windsor ON
The price is CA $71 per night from Nov 2 to Nov 3
CA $71
CA $110 total
Nov 2 - Nov 3
includes taxes & fees
Caesars Windsor Hotel & Casino - 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 CA $121 per night from Oct 29 to Oct 30
CA $121
CA $145 total
Oct 29 - Oct 30
includes taxes & fees
8.4/10 Very good! (1,381 reviews)
"There was no packing at the hotel premises. It had a smart TV, but it was not subscribed popular channels anything. The only programs you could watch come through the air (local programs)"

Reviewed on Oct 28, 2026

Best Western Plus Waterfront Hotel
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 CA $88 per night from Nov 22 to Nov 23
CA $88
CA $106 total
Nov 22 - Nov 23
includes taxes & fees
8.2/10 Very good! (1,635 reviews)
"The room was too small. You could only get off the beds on one side. The water pressure was not good in the bathroom plus the grout was black and dirty. One bed had a topper on it and the other one didn’t the swimming area was very good and the breakfast was very good. Also, there was only one chair ..."

Reviewed on Oct 27, 2026

Comfort Inn & Suites Ambassador Bridge
See all 471 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.
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Frequently asked questions

How much does a Maidstone vacation package cost?
Starting from as low as CA $992, 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.