Title: Windsor and Maidenhead Vacations & Trips 2026 from CA $1,681 | Expedia.ca [Windsor and Maidenhead Hotels](https://expedia.ca/Destinations-In-Windsor-And-Maidenhead.d553248635976996336.Hotel-Destinations)[Vacation Rentals in Windsor and Maidenhead](https://expedia.ca/Destinations-In-Windsor-And-Maidenhead.d553248635976996336.Vacation-Rental-Destinations)[Windsor and Maidenhead Car Rentals](https://expedia.ca/Destinations-In-Windsor-And-Maidenhead.d553248635976996336.Car-Rental-Destinations) ![](https://images.trvl-media.com/place/5479/deb199ae-19d7-4f63-b6a4-fdd57c4bd60a.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Windsor and Maidenhead Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Sasa Nikolic - ## 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 ## Top Windsor and Maidenhead Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Sloane Place](https://images.trvl-media.com/lodging/34000000/33780000/33770300/33770257/339a5668_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sloane Place London City Centre CA $1,681 per person Mar 19 - Mar 24 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to London (LHR) 9.2/10 Wonderful! (807 reviews) Room was comfortable, clean and homey. Staff were wonderful and the location is simply fantastic. Highly recommended place to stay for this part of London. Reviewed on Jan 25, 2026 ![Charles Hope Apartment Canary Wharf](https://images.trvl-media.com/lodging/60000000/59640000/59634700/59634631/b08c0f94_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Charles Hope Apartment Canary Wharf Canary Wharf CA $2,097 per person Mar 30 - Apr 9 found 8 hours ago Roundtrip non-stop flight included Montreal (YMQ) to London (LHR) 9.4/10 Exceptional! (14 reviews) Clean space, great view, easy check in + check out. Only thing it lacked was oven mitts (but that’s nitpicking). Will book again! Reviewed on Jan 26, 2026 ![Cleveland Residences Chelsea](https://images.trvl-media.com/lodging/102000000/101280000/101276700/101276648/5b674d3b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cleveland Residences Chelsea London City Centre CA $2,431 per person Mar 30 - Apr 9 found 8 hours ago Roundtrip non-stop flight included Montreal (YMQ) to London (LHR) 9.4/10 Exceptional! (19 reviews) Clean and bright felt safe location - kitchen facilities good - bed was fresh and clean - would be good to have had a long mirror Reviewed on Sep 10, 2025 ![Spacious 5 Bdrm Townhouse in Camden](https://images.trvl-media.com/lodging/118000000/117240000/117236200/117236178/daf758f7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Spacious 5 Bdrm Townhouse in Camden Camden CA $4,765 per person Mar 17 - Mar 25 found 6 hours ago Roundtrip non-stop flight included Montreal (YMQ) to London (LHR) No reviews ![One Bed Serviced Apartment in Chelsea](https://images.trvl-media.com/lodging/98000000/97590000/97586500/97586467/d6c2d15f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### One Bed Serviced Apartment in Chelsea London City Centre CA $3,028 per person Apr 24 - May 4 found 1 hour ago Roundtrip non-stop flight included Vancouver (YVR) to London (LHR) 6/10 (1 review) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_553248635976996336) ## Windsor and Maidenhead Hotel Deals ![De Vere Beaumont Estate](https://images.trvl-media.com/lodging/2000000/1780000/1775700/1775624/e2fc3664_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### De Vere Beaumont Estate Burfield Road, Berkshire Windsor England Fully refundableReserve now, pay when you stay CA $152 CA $182 total Feb 17 - Feb 18 includes taxes & fees 8/10 Very Good! (1,004 reviews) Amazing hotel and location. Staff were incredibly friendly and helpful. The pool and gym are excellent! Only downside to the bar is the don’t have Guinness on draft Reviewed on Feb 6, 2026 [](https://expedia.ca/Hotel-Search?startDate=17%2F02%2F2026&endDate=18%2F02%2F2026&selected=1775624&PinnedHotelID=1775624&HadPinnedHotel=true®ionId=553248635976996336) ![Sir Christopher Wren Hotel](https://images.trvl-media.com/lodging/1000000/50000/47800/47781/148298d0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sir Christopher Wren Hotel Thames Street Windsor England Fully refundableReserve now, pay when you stay CA $225 CA $270 total Feb 23 - Feb 24 includes taxes & fees 8.8/10 Excellent! (1,006 reviews) A beautiful hotel, fantastic location with great facilities and staff. Will definitely go there again. Reviewed on Feb 8, 2026 [](https://expedia.ca/Hotel-Search?startDate=23%2F02%2F2026&endDate=24%2F02%2F2026&selected=47781&PinnedHotelID=47781&HadPinnedHotel=true®ionId=553248635976996336) ![Harte and Garter](https://images.trvl-media.com/lodging/108000000/107550000/107546600/107546546/13a14b63_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Harte and Garter 31 High St Windsor England Fully refundableReserve now, pay when you stay CA $97 CA $117 total Mar 1 - Mar 2 includes taxes & fees 7.6/10 Good! (353 reviews) Excellent location and reasonably priced. Reviewed on Feb 4, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=107546546&PinnedHotelID=107546546&HadPinnedHotel=true®ionId=553248635976996336) [See all 524 properties in Windsor and Maidenhead](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=13%2F02%2F2026&endDate=14%2F02%2F2026®ionId=553248635976996336) 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 Windsor and Maidenhead vacation package cost? ### How do I get a cheap travel package to Windsor and Maidenhead? ### How far in advance should I book my Windsor and Maidenhead vacation? ### What does an Expedia Windsor and Maidenhead travel package include? ### What should I know before booking a Windsor and Maidenhead travel package? ### Can I choose my airline with a Windsor and Maidenhead Expedia vacation package? ### If I'm not able to travel, can I cancel my Windsor and Maidenhead vacation package? \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app