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.
Nicklin House

Nicklin House

3 out of 5
Price was CA $778, price is now CA $715 per person
CA $715
per person
Jul 18 - Jul 20
found 11 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Windsor (YQG)
9.4/10 Exceptional! (110 reviews)
A cozy house just south of downtown (just north of the ferry dock). We had the guest suite (downstairs), which had a minor disadvantage of pipes running across the ceiling, but otherwise, it was well soundproofed and got good light from outside. Breakfast was provided each morning and was a mix of berries, fruits, yoghurts, and scrambled eggs. The hosts (and their three dogs) ere wonderful people, very friendly, with a lot of hospitality experience. Would stay again!

Reviewed on Jun 15, 2026

Days Inn by Wyndham Leamington

Days Inn by Wyndham Leamington

2.5 out of 5
Price was CA $898, price is now CA $845 per person
CA $845
per person
Jul 18 - Jul 20
found 11 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Windsor (YQG)
7.8/10 Good! (940 reviews)
Very friendly, helpful staff. Comfortable and quiet !!

Reviewed on May 16, 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 $903, price is now CA $850 per person
CA $850
per person
Jul 18 - Jul 20
found 11 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Windsor (YQG)
9.4/10 Exceptional! (1,008 reviews)
Customer service very friendly and helpful Rooms were very clean

Reviewed on Jun 11, 2026

Coastal #1 and Cozy #2 - Seacliff Beach Suites

Coastal #1 and Cozy #2 - Seacliff Beach Suites

3.5 out of 5
Price was CA $1,077, price is now CA $1,020 per person
CA $1,020
per person
Jul 18 - Jul 20
found 11 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Windsor (YQG)
10/10 Exceptional! (12 reviews)
The place is perfect. Nice kitchen nice bathroom and clean .

Reviewed on Dec 13, 2025

Seacliffe Inn

Seacliffe Inn

3 out of 5
Price was CA $1,062, price is now CA $1,011 per person
CA $1,011
per person
Jul 20 - Jul 23
found 9 hours ago
Roundtrip flight included
Toronto (YYZ) to Windsor (YQG)
8/10 Very Good! (1,006 reviews)
Excellent location, friendly staff.

Reviewed on Jun 15, 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 $79 per night from Jul 13 to Jul 14
CA $79
CA $120 total
Jul 13 - Jul 14
includes taxes & fees
8.6/10 Excellent! (3,338 reviews)
"There was some issue with power but everything else was excellent!!"

Reviewed on Jun 16, 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 CA $155 per night from Jun 28 to Jun 29
CA $155
CA $186 total
Jun 28 - Jun 29
includes taxes & fees
9.2/10 Wonderful! (1,104 reviews)
"Room was very clean"

Reviewed on Jun 16, 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 CA $103 per night from Jul 13 to Jul 14
CA $103
CA $123 total
Jul 13 - Jul 14
includes taxes & fees
8/10 Very Good! (1,448 reviews)
"Room was clean and AC worked well."

Reviewed on Jun 16, 2026

Comfort Inn & Suites Ambassador Bridge
See all 464 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 $715, 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.