Maidstone Vacations from $486
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
The Latest Maidstone Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel STRY
$547
per person
Oct 29 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Bakersfield (BFL) to Windsor (YQG)
10/10 Exceptional! (37 reviews)
Check was very easy. Room was beautifully decorated and very large. We liked the kitchen and the ability to
make our morning coffee was a lovely feature. It is located in a great area and lots of restaurants and parks are within walking distance
Reviewed on Aug 14, 2026
Maidstone Hotel Deals
Caesars Windsor Hotel & Casino - A Caesars Rewards Destination
377 Riverside Dr E Windsor ON
$68 nightly
$81 total
Aug 17 - Aug 18
Total with taxes and fees
8.6/10 Excellent! (3,357 reviews)
"N"
Reviewed on Aug 15, 2026
Best Western Plus Waterfront Hotel
277 Riverside Drive West Windsor ON
Fully refundableReserve now, pay when you stay
$96 nightly
$115 total
Aug 25 - Aug 26
Total with taxes and fees
Holiday Inn Express Windsor Waterfront by IHG
33 Riverside Drive East Windsor ON
Fully refundable
$100 nightly
$120 total
Sep 1 - Sep 2
Total with taxes and 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.
Explore a world of travel with Expedia
- Flights to Town of Essex
- Westjet Calgary (YYC) to Windsor (YQG) flights
- Flights from Newark Liberty Intl. Airport (EWR) to Windsor (YQG)
- Flights from Edmonton (YEG) to Windsor (YQG)
- Flights from Atlanta (ATL) to Windsor (YQG)
- Flights from Boston (BOS) to Windsor (YQG)
- Flights from Columbus (CMH) to Windsor (YQG)
- Flights from Amman (AMM) to Windsor (YQG)
- Flights from Chilliwack (YCW) to Windsor (YQG)
- Flights from Detroit (DTW) to Windsor (YQG)
- Flights from Philadelphia (PHL) to Windsor (YQG)
- Flights from Cincinnati (CVG) to Windsor (YQG)
- Air Canada Toronto (YYZ) to Windsor (YQG) flights
- Flights from San Francisco (SFO) to Windsor (YQG)
- Flights from Houston (IAH) to Windsor (YQG)
- Flights from Hartford (BDL) to Windsor (YQG)
- Flights from Seattle (SEA) to Windsor (YQG)
- Flights from Phoenix (PHX) to Windsor (YQG)
- Flights from Beirut (BEY) to Windsor (YQG)
- Flights from Lahore (LHE) to Windsor (YQG)
- Flights from Indianapolis (IND) to Windsor (YQG)
- Flights from Halifax (YHZ) to Windsor (YQG)
- Flights from Toronto (YYZ) to Windsor (YQG)
- Flights from Calgary (YYC) to Windsor (YQG)
- Flights from Milwaukee (MKE) to Windsor (YQG)
- Flights from Dallas (DFW) to Windsor (YQG)
- Flights from Minneapolis (MSP) to Windsor (YQG)
- Flights from Ottawa (YOW) to Windsor (YQG)
- Flights from New York (JFK) to Windsor (YQG)
- Flights from Honolulu (HNL) to Windsor (YQG)
- Flights from Cleveland (CLE) to Windsor (YQG)
- Flights from Orlando (MCO) to Windsor (YQG)
- Flights from Dhaka (DAC) to Windsor (YQG)
- Flights from Adelaide (ADL) to Windsor (YQG)
- Flights from Las Vegas (LAS) to Windsor (YQG)
- Flights from San Diego (SAN) to Windsor (YQG)
- Flights from Kelowna (YLW) to Windsor (YQG)
- Flights from Vancouver (YVR) to Windsor (YQG)
- Flights from Los Angeles (LAX) to Windsor (YQG)
- Flights from London (YXU) to Windsor (YQG)
- Flights from Montreal (YUL) to Windsor (YQG)
- Flights from St. Louis (STL) to Windsor (YQG)
- Porter Airlines Toronto (YTZ) to Windsor (YQG) flights
- Flights from Chatham (XCM) to Windsor (YQG)
- Flights to Windsor
- Flights from Denver (DEN) to Windsor (YQG)
- Flights from Syracuse (SYR) to Windsor (YQG)
- Flights from Baltimore (BWI) to Windsor (YQG)
- Flights from Chicago (ORD) to Windsor (YQG)
- Flights from Hamilton (YHM) to Windsor (YQG)
- Flights from Washington (IAD) to Windsor (YQG)
- Flights from Windsor
- Flights from Colombo (CMB) to Windsor (YQG)
- 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.