Maidstone Vacation Packages
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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.
Top Holiday Package Deals in Maidstone
Price found within the past 48 hours. Click for updated prices.
Hotel STRY
Price was CA $2,069, price is now CA $1,829 per person
CA $1,829
per person
Dec 24 - Dec 28
found 21 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Windsor (YQG)
10/10 Exceptional! (46 reviews)
I almost don’t want to share how spectacular Hotel STRY is! I will make a point to book this hotel every single time I am in this area. I will drive from Windsor just to stay here. If you have the pleasure of meeting Cat, she is amazing and will take care of all your needs. This is a Must Stay if you are anywhere near Amherstburg!
Reviewed on Oct 30, 2026
Towneplace Suites By Marriott Tecumseh Windsor
Price was CA $1,646, price is now CA $1,515 per person
CA $1,515
per person
Dec 24 - Dec 28
found 21 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Windsor (YQG)
9.6/10 Exceptional! (179 reviews)
Beautiful, new, very clean and modern hotel! Room was very spacious and beds were very comfortable! Great amenities including a pool and gym. Lobby and hotel bar were inviting and created a great social environment. Staff were incredible from the front desk, bar staff and even the housekeeping lady who offered us Halloween chocolate!
Would stay hear again in a heartbeat!!!
Reviewed on Oct 29, 2026
Dream Estate Inn
Price was CA $1,084, price is now CA $1,051 per person
CA $1,051
per person
Dec 11 - Dec 13
found 1 hour ago
Roundtrip non-stop flight included
Calgary (YYC) to Windsor (YQG)
9.4/10 Exceptional! (142 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
377 Riverside Dr E Windsor ON
The price is CA $63 per night from Nov 30 to Dec 1
CA $63
CA $101 total
Nov 30 - Dec 1
includes taxes & fees
8.8/10 Excellent! (3,595 reviews)
"Nice option to have valet and someone to take your things to your room for a fee. the walk was very very long from the valet to the room in the Forum tower. If you have someone with you that has walking challenges, you may want to ask about wheelchair access ahead of time. The Vu bar with a view ..."
Reviewed on Oct 30, 2026
Best Western Plus Waterfront Hotel
277 Riverside Drive West Windsor ON
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from Nov 8 to Nov 9
CA $134
CA $161 total
Nov 8 - Nov 9
includes taxes & fees
Comfort Inn & Suites Ambassador Bridge
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
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.
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.