Maidstone Vacations from $523
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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.
The Latest Maidstone Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Towneplace Suites By Marriott Tecumseh Windsor
Price was $523, price is now $523 per person
$523
per person
Aug 2 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Windsor (YQG)
9.8/10 Exceptional! (91 reviews)
The hotel was very clean and staff was friendly.
Reviewed on Jun 13, 2026
Holiday Inn Express & Suites Windsor East - Lakeshore by IHG
Price was $591, price is now $553 per person
$553
per person
Aug 2 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Windsor (YQG)
9.4/10 Exceptional! (1,016 reviews)
Clean property and has a very nice walking in shower
Reviewed on Jun 19, 2026
Maidstone Hotel Deals
Best Western Plus Waterfront Hotel
277 Riverside Drive West Windsor ON
Fully refundableReserve now, pay when you stay
$78 nightly
The price is $93 total per night from Jun 25 to Jun 26
$93 total
Jun 25 - Jun 26
Total with taxes and fees
8.2/10 Very Good! (1,020 reviews)
"It was a nice hotel. Everything was lovely."
Reviewed on Jun 21, 2026
Caesars Windsor - A Caesars Rewards Destination
377 Riverside Dr E Windsor ON
$70 nightly
The price is $84 total per night from Jul 21 to Jul 22
$84 total
Jul 21 - Jul 22
Total with taxes and fees
8.6/10 Excellent! (3,282 reviews)
"Nice"
Reviewed on Jun 22, 2026
DoubleTree by Hilton Windsor Hotel & Suites
333 Riverside Dr W Windsor ON
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $132 total per night from Jun 28 to Jun 29
$132 total
Jun 28 - Jun 29
Total with taxes and fees
9.2/10 Wonderful! (1,114 reviews)
"The staff was very helpful. Tge facility was excellent and tge breakfast buffet was great"
Reviewed on Jun 21, 2026
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.
Discover the most popular places to visit in Maidstone
Ciocairo Club of Windsor
Why not roll the dice with a visit to Ciocairo Club of Windsor during your time in Tecumseh? Amble around this vibrant area's riverfront or experience its acclaimed theater scene.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.