Title: Old Windsor Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $1,782 Expedia.ca [Old Windsor Travel Guide](https://expedia.ca/Windsor-Old-Windsor.dx6056735)[Hotels in Old Windsor](https://expedia.ca/Old-Windsor-Windsor-Hotels.0-n6056735-0.Travel-Guide-Filter-Hotels)[Flights to Windsor](https://expedia.ca/Cheap-Flights-To-Windsor.d5479.Travel-Guide-Flights)[Things to do in Windsor](https://expedia.ca/Things-To-Do-In-Windsor.d5479.Travel-Guide-Activities)[Old Windsor Car Rentals](https://expedia.ca/Car-Rentals-In-Old-Windsor.d6056735.Car-Rental-Guide) ![](https://images.trvl-media.com/place/4271/40489cda-fa9c-4677-80ea-f75eb55e3fa4.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Old Windsor Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Tristan Young - ## 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 Old Windsor Vacation Say farewell to planning worries and hello to a Old Windsor vacation package. With the finer details organized before you take off, you can focus on discovering this city, starting with Brookwood, which is great for hiking, adventure sports and golfing. If sightseeing is part of the plan during your trip to Old Windsor, stop by leading attractions like [Windsor Castle](https://www.expedia.ca/Windsor-Castle-Windsor-City-Centre.d501522.Vacation-Attraction), [LEGOLAND® Windsor](https://www.expedia.ca/LEGOLAND-Windsor-Windsor.d6083947.Vacation-Attraction) and [Frogmore House](https://www.expedia.ca/Frogmore-House-Windsor.d6083937.Vacation-Attraction). Stop daydreaming and start adventuring. Explore the wide range of options on Expedia today and put your Old Windsor vacation plans into gear! ## Top Holiday Package Deals in Old Windsor Price found within the past 48 hours. Click for updated prices. ![Croydon by Charles Hope](https://images.trvl-media.com/lodging/101000000/100580000/100572100/100572019/f6efcc40_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Croydon by Charles Hope Fairfield CA $1,782 per person May 14 - May 20 found 1 day ago Roundtrip flight included Toronto (YTZ) to London (LHR) 8.6/10 Excellent! (18 reviews) Great property in a great location. Apart from a few minor broken things in the unit, it was clean, comfortable and had everything we needed. Will certainly be back! Reviewed on Jul 4, 2025 ![The George Street Residences](https://images.trvl-media.com/lodging/105000000/104380000/104375500/104375483/w1534h1024x0y0-1b8124a9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The George Street Residences London City Centre CA $4,013 per person May 28 - Jun 3 found 9 hours ago Roundtrip non-stop flight included Toronto (YYZ) to London (LHR) No reviews ![The Princes Residences](https://images.trvl-media.com/lodging/105000000/104380000/104372800/104372797/7a554ac7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Princes Residences London City Centre CA $3,435 per person May 28 - Jun 3 found 9 hours ago Roundtrip non-stop flight included Toronto (YYZ) to London (LHR) No reviews ![The Chesham Residences](https://images.trvl-media.com/lodging/105000000/104280000/104280000/104279965/593c4c6a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Chesham Residences London City Centre CA $4,588 per person May 28 - Jun 3 found 9 hours ago Roundtrip non-stop flight included Toronto (YYZ) to London (LHR) 6/10 (2 reviews) The flat was spacious, clean, ans well furnished. My issue is the communication. The lights in the kitchen did not work the entire week. I reached out to the management company via email, portal, and Expedia multiple times, all without response. We were not able to fix a meal after sundown and my wife nearly fell on the stairs due to the lack of light. It should have been an easy solve and I hope they fixed it for the next person. Reviewed on Apr 13, 2025 ![The Mayfair Collection](https://images.trvl-media.com/lodging/105000000/104440000/104437000/104436980/f5fdd424_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Mayfair Collection London City Centre CA $2,187 per person May 28 - Jun 3 found 9 hours ago Roundtrip non-stop flight included Toronto (YYZ) to London (LHR) No reviews ## Where to stay in Old Windsor Find the best Old Windsor areas and neighborhoods for the activities you enjoy most. [Learn more about Old Windsor](https://expedia.ca/Windsor-Old-Windsor.dx6056735) ![Windsor Castle showing château or palace and heritage architecture](https://images.trvl-media.com/place/501522/3d7227c1-1ad7-442a-9d31-8640104b027b.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Windsor City Centre 2 out of top 10 points of interest in this area 4.5/5(16 area reviews) The lively bars and stunning river views are top of the list for many visitors to Windsor City Centre. A stop by Thames Path or Thames River might round out your trip. [Find hotel + flight trips in Windsor City Centre](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Windsor%20City%20Centre&DestID=553248635810423668&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Eton](https://images.trvl-media.com/place/11950/9be42729-a897-4609-ac2f-9e72d9e56963.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Eton 1 out of top 10 points of interest in this area Explore this town’s enchanting high street for galleries and pubs. Learn about six centuries of the iconic college’s history and its famous alumni. [Find hotel + flight trips in Eton](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Eton&DestID=11950&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Windsor Great Park](https://images.trvl-media.com/place/915362425499639808/a3329362-21a7-4612-ab5d-1ae3024ba9d5.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Park If you're looking for some top things to see and do in Park and surrounding area, you can visit LEGOLAND® Windsor and Windsor Great Park. [Find hotel + flight trips in Park](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Park&DestID=915362425499639808&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Aerial view of the Windsor castle and the river Thames](https://images.trvl-media.com/place/915187318353395712/769639f2-5b46-48c1-bf13-541b5dc35181.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Clewer East Clewer East might not have many top sights, but LEGOLAND® Windsor and Windsor Racecourse are two attractions nearby that you can check out. [Find hotel + flight trips in Clewer East](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Clewer%20East&DestID=915187318353395712&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Windsor marina . ](https://images.trvl-media.com/place/5479/37f49b68-15dc-4a20-ad4f-56c90f7c91bb.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Clewer North 1 out of top 10 points of interest in this area While visiting Clewer North, you might make a stop by sights like Windsor Racecourse and Thames Path. [Find hotel + flight trips in Clewer North](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Clewer%20North&DestID=915186833745711104&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Old Windsor Hotel Deals ![Royal Garden Hotel](https://images.trvl-media.com/lodging/1000000/60000/55000/54987/86ea6f58_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Royal Garden Hotel 2-24 Kensington High Street London England Fully refundableReserve now, pay when you stay CA $264 CA $317 total Mar 15 - Mar 16 includes taxes & fees 9.2/10 Wonderful! (1,844 reviews) Fantastic staff, amazing room view and location Reviewed on Mar 13, 2026 [](https://expedia.ca/Hotel-Search?startDate=15%2F03%2F2026&endDate=16%2F03%2F2026&selected=54987&PinnedHotelID=54987&HadPinnedHotel=true®ionId=6056735) ![ The Drey - Kensington, Earl's Court](https://images.trvl-media.com/lodging/119000000/118960000/118958900/118958877/f6e696d3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Drey - Kensington, Earl's Court 1 Barkston Gardens London England Fully refundable CA $139 CA $167 total Mar 23 - Mar 24 includes taxes & fees 9/10 Wonderful! (135 reviews) This is a fabulous stay. On a quiet street near the underground. Not a far trip anywhere. Rooms are a great size! Definitely recommend! Reviewed on Mar 13, 2026 [](https://expedia.ca/Hotel-Search?startDate=23%2F03%2F2026&endDate=24%2F03%2F2026&selected=118958877&PinnedHotelID=118958877&HadPinnedHotel=true®ionId=6056735) ![Copthorne Tara Hotel London Kensington](https://images.trvl-media.com/lodging/1000000/30000/26200/26145/a8cf46a6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Copthorne Tara Hotel London Kensington Scarsdale Place London England Fully refundableReserve now, pay when you stay CA $102 CA $122 total Mar 22 - Mar 23 includes taxes & fees 7.8/10 Good! (3,534 reviews) Good clean and service Reviewed on Mar 13, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&selected=26145&PinnedHotelID=26145&HadPinnedHotel=true®ionId=6056735) [See all 17,068 properties in Old Windsor](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=14%2F03%2F2026&endDate=15%2F03%2F2026®ionId=6056735) 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 an Old Windsor vacation package cost? ### What are the cheapest months to go to Old Windsor? ### How many days is enough for Old Windsor? ### Is it worth booking a vacation package to Old Windsor? ### How to find the best Old Windsor package deals? ### Is it cheaper to book an Old Windsor vacation as a package? ### When to book a vacation package to Old Windsor? ### How to plan a trip to Old Windsor? > 1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Old Windsor. > 2. Plan your budget wisely: On top of the cost of your hotel, you'll need to consider other expenses too. These include flights, transportation and food. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Old Windsor. > 3. Decide how long to go away for: Now that you're more familiar with Old Windsor, you can work out the right length of your break. Put together a draft itinerary and allocate enough time for all the things you want to do. > 4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a customized Old Windsor vacation package. ### Things to do ![LEGOLAND® Windsor Resort Tickets](https://mediaim.expedia.com/localexpert/509407/12ed7808-635c-433a-a4d4-c998acab4b89.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### LEGOLAND® Windsor Resort Tickets CA $59 per traveller **78%** of travellers recommend [](https://expedia.ca/things-to-do/legoland-windsor-resort-tickets.a509407.activity-details) ![sunset at Windsor Castle in London](https://mediaim.expedia.com/localexpert/169694/4fe79ceb-570e-4a4b-825d-44ad6fd3554f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Windsor Castle Admission Tickets CA $59 per adult **82%** of travellers recommend [](https://expedia.ca/things-to-do/windsor-castle-admission-tickets.a169694.activity-details) ![young boy poses next to Lego Pirate at Lego Land in London](https://mediaim.expedia.com/localexpert/169894/b52f8731-dd1f-457a-ba58-463307013177.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Legoland® Windsor with Roundtrip Transportation CA $146 per adult **74%** of travellers recommend [](https://expedia.ca/things-to-do/legoland-windsor-with-roundtrip-transportation.a169894.activity-details) [See all activities in Windsor](https://expedia.ca/things-to-do/search?rid=6056735) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.