Maidstone Vacations from $895
Book a Hotel + Flight or Car together to unlock savings
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.
Town N Country Motor Inn
Price was $895, price is now $895 per person
$895
per person
May 2 - May 6
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) to Windsor (YQG)
8/10 Very Good! (75 reviews)
Please be aware of bringing your own coffee or tea bags, as there is only coffee machine.
Reviewed on Mar 13, 2026
Park Bungalow #4 - Seacliff Beach Suites
Price was $1,588, price is now $1,389 per person
$1,389
per person
May 2 - May 6
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) to Windsor (YQG)
9.6/10 Exceptional! (15 reviews)
The property is super clean. Walking distance to the parks. Gas stations, groceries shopping are all closed by.
Reviewed on Jul 28, 2025
Dream Estate Inn
Price was $1,155, price is now $1,011 per person
$1,011
per person
May 2 - May 6
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) to Windsor (YQG)
9.4/10 Exceptional! (127 reviews)
This was a lovely place to stay. The room was spacious, comfortable, ultra clean and had a little gratitude practice available to guests. While the bed and breakfast is self serve, the complementary items were healthy, easy and convenient. This is a lovely place with a lot of thoughtful touches. I highly recommend this hidden gem in Leamington Ontario.
Reviewed on Nov 5, 2025
Days Inn by Wyndham Leamington
Price was $1,071, price is now $1,057 per person
$1,057
per person
May 2 - May 6
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) to Windsor (YQG)
7.8/10 Good! (921 reviews)
Very clean, basic hotel. The staff were all incredibly friendly & helpful (Anun gave me both bakery and restaurant recommendations that were excellent).
It was the perfect spot to stay for a hockey tournament.
Reviewed on Mar 10, 2026
Maidstone Hotel Deals
Caesars Windsor - A Caesars Rewards Destination
377 Riverside Dr E Windsor ON
$109 nightly
The price is $130 total per night from Apr 12 to Apr 13
$130 total
Apr 12 - Apr 13
Total with taxes and fees
8.6/10 Excellent! (3,190 reviews)
Quiet, clean, and nice view
Reviewed on Mar 13, 2026
Best Western Plus Waterfront Hotel
277 Riverside Drive West Windsor ON
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $91 total per night from Mar 16 to Mar 17
$91 total
Mar 16 - Mar 17
Total with taxes and fees
8.2/10 Very Good! (1,006 reviews)
No microwaves but great stay
Reviewed on Mar 13, 2026
Holiday Inn Express Windsor Waterfront by IHG
33 Riverside Drive East Windsor ON
Fully refundable
$99 nightly
The price is $119 total per night from Mar 15 to Mar 16
$119 total
Mar 15 - Mar 16
Total with taxes and fees
8.6/10 Excellent! (1,360 reviews)
Well kept
Reviewed on Mar 13, 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 great live music.
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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.