Maidstone Vacations from $717
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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.
Hotel STRY
$935
per person
Oct 12 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Windsor (YQG)
10/10 Exceptional! (41 reviews)
The STRY is a wonderful gem in a lovely little town at the best location possible! This magnificent boutique hotel is owner-managed by a sweet and warm family who rightfully take pride in their labor of love! The design - our room, rooms we got a glimpse of, the great restaurant and everything in between is brilliant with as much attention to detail as artistic creativity! Each and every staff person is welcoming and professional. Of course you should also make sure to eat at The Missing O - great food and vibe! Start to finish, we had a wonderful experience and wholeheartedly recommend the STRY to others!!
Reviewed on Aug 26, 2026
Maidstone Hotel Deals
Caesars Windsor Hotel & Casino - A Caesars Rewards Destination
377 Riverside Dr E Windsor ON
$63 nightly
$75 total
Sep 2 - Sep 3
Total with taxes and fees
Best Western Plus Waterfront Hotel
277 Riverside Drive West Windsor ON
Fully refundableReserve now, pay when you stay
$97 nightly
$116 total
Sep 7 - Sep 8
Total with taxes and fees
Holiday Inn Express Windsor Waterfront by IHG
33 Riverside Drive East Windsor ON
Fully refundable
$97 nightly
$116 total
Sep 4 - Sep 5
Total with taxes and fees
8.8/10 Excellent! (1,445 reviews)
"Wasn’t in the best area but once you’re inside, it’s great!"
Reviewed on Aug 25, 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.
Explore a world of travel with Expedia
- Flights to Town of Essex
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- Visit Windsor
- Serenity Lavender Farm
- North 42 Degrees Estate Winery
- Adventure Bay Family Water Park
- Walkerville Brewery
- Wheatley Provincial Park
- Buxton National Historic Site & Museum
- Pelee Island Winery
- Gordon House
- Colio Estate Winery
- Dieppe Gardens
- Leamington Municipal Marina
- Leamington Vacations
- Windsor Riverfront
- Sprucewood Shores Estate Winery
- Kingsville Vacations
- Detroit Windsor Tunnel
- Windsor Vacations
- East Windsor Vacations
- Olde Walkerville Neighborhood
- Coventry Gardens
- Tecumseh Vacations
- Ontario Travel Information Centre - Windsor
- Chatham-Kent Vacations
- Chatham-Kent Museum
- Point Pelee National Park
- Caesars Casino
- Cottam Vacations
- Wheatley Harbour
- Ambassador Bridge
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.