Maidstone Vacation Packages 2026

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
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.

Maidstone Hotel Deals

Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

377 Riverside Dr E Windsor ON

$59 nightly

$71 total

Nov 2 - Nov 3

Total with taxes and fees

8.8/10 Excellent! (3,532 reviews)

"Confusion checking in as we had 2,rooms. Have a brother with dementia so the PSW stayed with him while I checked in. Not till we got to our room did we realize the only have is 1 rooms let. Went all the way back to reception to find out the PSW was to check in also. Proper customer service would ..."

Reviewed on Oct 3, 2026

Best Western Plus Waterfront Hotel

277 Riverside Drive West Windsor ON

Fully refundableReserve now, pay when you stay

$94 nightly

$113 total

Oct 9 - Oct 10

Total with taxes and fees

Holiday Inn Express Windsor Waterfront by IHG

33 Riverside Drive East Windsor ON

Fully refundable

$95 nightly

$113 total

Nov 1 - Nov 2

Total with taxes and fees

See all 473 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.