Title: Maidstone Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $1,072 Expedia.ca [Hotels in Maidstone](https://expedia.ca/Maidstone-Tecumseh-Hotels.0-n3000408290-0.Travel-Guide-Filter-Hotels)[Flights to Tecumseh](https://expedia.ca/Cheap-Flights-To-Tecumseh.d6003759.Travel-Guide-Flights)[Maidstone Car Rentals](https://expedia.ca/Car-Rentals-In-Maidstone.d3000408290.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Maidstone Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 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](https://www.expedia.ca/McAuliffe-Woods-Conservation-Area-Trail-Trailhead-Windsor.d642981843593011200.Vacation-Attraction). 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. ![Nicklin House](https://images.trvl-media.com/lodging/49000000/48230000/48225800/48225738/ac065fb6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Nicklin House CA $1,072 per person Mar 29 - Apr 1 found 1 day ago Roundtrip flight included Charlottetown (YYG) to Windsor (YQG) 9.2/10 Wonderful! (92 reviews) Clean and peaceful place. Reviewed on Nov 23, 2025 ![Seacliffe Inn](https://images.trvl-media.com/lodging/4000000/3150000/3144300/3144232/ddc19b3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Seacliffe Inn CA $1,215 per person Mar 29 - Apr 1 found 1 day ago Roundtrip flight included Charlottetown (YYG) to Windsor (YQG) 8.2/10 Very Good! (1,000 reviews) Clean quiet comfortable bed and nice gas fireplace. Easy parking Reviewed on Feb 16, 2026 ![Dream Estate Inn](https://images.trvl-media.com/lodging/96000000/96000000/95995200/95995136/ee81656e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Dream Estate Inn CA $1,198 per person Mar 29 - Apr 1 found 1 day ago Roundtrip flight included Charlottetown (YYG) to Windsor (YQG) 9.4/10 Exceptional! (123 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 ![Parkside Flat #5 - Seacliff Beach Suites](https://images.trvl-media.com/lodging/105000000/104200000/104193100/104193053/3cdbfbcd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Parkside Flat #5 - Seacliff Beach Suites CA $1,203 per person Mar 29 - Apr 1 found 1 day ago Roundtrip flight included Charlottetown (YYG) to Windsor (YQG) 10/10 Exceptional! (3 reviews) Very close to beach. Nice and clean place to stay ☺️ Reviewed on Jul 11, 2024 ## Maidstone Hotel Deals ![Caesars Windsor - A Caesars Rewards Destination](https://images.trvl-media.com/lodging/3000000/2240000/2232500/2232457/8112ff17_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Caesars Windsor - A Caesars Rewards Destination 377 Riverside Dr E Windsor ON CA $159 CA $219 total Feb 23 - Feb 24 includes taxes & fees 8.6/10 Excellent! (3,203 reviews) Was what id expected. But there is NO noise barrier between adjoining rooms or between rooms and hallway. You hear a LOT! Ive never stayed before. It was a valentines day treat. View was what i wanted. Room was comfortable. But i paid $350 for one night! No robe in the room, only one comfortable ... Reviewed on Feb 22, 2026 [](https://expedia.ca/Hotel-Search?startDate=23%2F02%2F2026&endDate=24%2F02%2F2026&selected=2232457&PinnedHotelID=2232457&HadPinnedHotel=true®ionId=3000408290) ![Best Western Plus Waterfront Hotel](https://images.trvl-media.com/lodging/1000000/20000/11000/10954/a3d331c0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Plus Waterfront Hotel 277 Riverside Drive West Windsor ON Fully refundableReserve now, pay when you stay CA $103 CA $124 total Mar 8 - Mar 9 includes taxes & fees 8.2/10 Very Good! (1,009 reviews) Room was ok. Toilet seemed like it was going to overflow every time you flushed! The bathroom could use some updating. Reviewed on Feb 22, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F03%2F2026&endDate=09%2F03%2F2026&selected=10954&PinnedHotelID=10954&HadPinnedHotel=true®ionId=3000408290) ![Holiday Inn Express Windsor Waterfront by IHG](https://images.trvl-media.com/lodging/1000000/30000/21500/21423/61671e42_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Express Windsor Waterfront by IHG 33 Riverside Drive East Windsor ON Fully refundable CA $143 CA $172 total Feb 25 - Feb 26 includes taxes & fees 8.6/10 Excellent! (1,380 reviews) Very clean, clean and modern building Reviewed on Feb 8, 2026 [](https://expedia.ca/Hotel-Search?startDate=25%2F02%2F2026&endDate=26%2F02%2F2026&selected=21423&PinnedHotelID=21423&HadPinnedHotel=true®ionId=3000408290) [See all 420 properties in Maidstone](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=23%2F02%2F2026&endDate=24%2F02%2F2026®ionId=3000408290) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Frequently asked questions ### How much does a Maidstone vacation package cost? ### How do I get a cheap travel package to Maidstone? ### How far in advance should I book my Maidstone vacation? ### What does an Expedia Maidstone travel package include? ### What should I know before booking a Maidstone travel package? ### Can I choose my airline with a Maidstone Expedia vacation package? ### If I'm not able to travel, can I cancel my Maidstone vacation package? \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.