Title: Book the Best Windsor Hotels with Early Check-in in 2026 | Expedia.ca [Windsor Travel Guide](https://expedia.ca/Windsor.dx5479)[Hotels in Windsor](https://expedia.ca/Windsor-Hotels.d5479.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.ca/Windsor-Vacation-Rentals.d5479.Travel-Guide-VacationRentals)[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)[Windsor Car Rentals](https://expedia.ca/Car-Rentals-In-Windsor.d5479.Car-Rental-Guide)[Windsor Vacation Packages](https://expedia.ca/Windsor.d5479.Destination-Travel-Guides) ![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=1200&h=500&q=medium) # Find Hotels with Early Check-in in Windsor - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Windsor Hotels with Early Check-in Tonight [Dec 21 - Dec 22](https://www.expedia.ca/Hotel-Search?regionId=5479&startDate=2025-12-21&endDate=2025-12-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 22 - Dec 23](https://www.expedia.ca/Hotel-Search?regionId=5479&startDate=2025-12-22&endDate=2025-12-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=5479&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=5479&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Find out more about Windsor ### Discover top Windsor attractions Windsor is a paradise of experiences that cater to discerning travellers seeking both culture and comfort. Begin your adventure at the grand Windsor Castle, the oldest and largest inhabited castle in the world, where you can explore the lavish State Apartments and catch the Changing of the Guard ceremony. Just a short stroll away is the picturesque Long Walk, a stunning tree-lined avenue that invites leisurely strolls, perfect for families wanting to soak in the natural beauty and charm of the area. For a slice of history combined with modern flair, visit the Windsor Royal Shopping, where you can indulge in boutique shopping, savour delightful dining options, and even enjoy a film at the local cinema. Thrill-seekers will appreciate the nearby Legoland Windsor, offering a magical day out for children with its thrilling rides and interactive experiences. After a day of exploration, consider staying in the heart of Windsor, where options like the luxurious Macdonald Windsor Hotel provide an exquisite blend of comfort and convenience—enjoying a relaxing evening in their stylish rooms or dining in their acclaimed restaurant. With easy access to all the main attractions, you’ll feel pampered and well cared for, making your visit to Windsor an effortless delight. ### Find the best hotels with early check-in in Windsor For travellers seeking flexibility during their stay in Windsor, these top hotels offer convenient early check-in options. Enjoy a seamless experience with amenities tailored to your schedule. [**The Winning Post**](https://www.expedia.ca/Windsor-Hotels-The-Winning-Post.h4430939.Hotel-Information) - **Why it's great for flexible check-in:** The Winning Post is an excellent choice for travellers looking for early check-in flexibility, a rating of 9.2\. This traditional hotel allows guests to check in early, ensuring a straightforward arrival when exploring the scenic surroundings of Windsor. - **Other amenities:** The hotel features a lovely terrace, onsite parking, and complimentary toiletries. Guests can enjoy nearby winery tours, and the serene garden provides a peaceful escape. Additional offerings include daily housekeeping, premium bedding for a restful night's sleep, and a pet-friendly policy for those travelling with service animals. - **Nearby attractions:** Lapland UK - 5.5 km, LEGOLAND® Windsor - 5.9 km, Royal Ascot Golf Club - 6 km [**Goswell House**](https://www.expedia.ca/Windsor-Hotels-Goswell-House.h57751774.Hotel-Information) - **Why it's great for flexible check-in:** With a stellar review rating of 9.2, Goswell House stands out as a welcoming option for those needing early check-in. The hotel offers express check-in services designed to streamline your arrival, allowing guests to settle in quickly and enjoy their visit to Windsor. - **Other amenities:** The hotel features daily housekeeping, air conditioning for comfort, and is conveniently located near shopping districts. Guests can also benefit from breakfast options tailored for children, enhancing the family-friendly atmosphere. Its nearby the historical district adds to the charm of this inviting hotel. - **Neighborhood:** Windsor City Centre - **Nearby attractions:** St. Georges Chapel - 0.2 km, Theatre Royal - 0.2 km, Windsor Castle - 0.1 km [**Castle Hotel Windsor**](https://www.expedia.ca/Windsor-Hotels-Castle-Hotel-Windsor-MGallery.h16500.Hotel-Information) - **Why it's great for flexible check-in:** The Castle Hotel Windsor is a fantastic choice for those who value early check-in, offering a convenient check-in time to suit your travel plans. With an impressive guest review rating of 9.0, this luxurious hotel provides a range of amenities including late check-out options that allow guests to maximise their time in this beautiful city. - **Other amenities:** Guests can enjoy a delightful terrace, electric car charging stations, and self-parking facilities. The hotel is situated in a historic district, perfect for exploring Windsor's rich heritage. Additional offerings include 24-hour room service, daily housekeeping, and access to nearby golf facilities, ensuring a comfortable and enjoyable stay. - **Neighborhood:** Windsor City Centre - **Nearby attractions:** St. Georges Chapel - 0.3 km, Theatre Royal - 0.3 km, Windsor Castle - 0.2 km [**Sir Christopher Wren Hotel**](https://www.expedia.ca/Windsor-Hotels-Sir-Christopher-Wren-Hotel.h47781.Hotel-Information) - **Why it's great for flexible check-in:** Sir Christopher Wren Hotel welcomes guests with an early check-in option, allowing for a smooth start to your stay. Rated 8.8 by guests, this sophisticated hotel is located in the heart of Windsor, making it an ideal base for exploration while enjoying the comfort of late check-out as well. - **Other amenities:** The hotel features a lovely terrace, complimentary breakfast, and a selection of designer toiletries. Guests can take advantage of free parking nearby, a health club for fitness enthusiasts, and a garden for relaxation. With 24-hour room service and kid-friendly meal options at the restaurant, the hotel caters to diverse needs while ensuring a pleasant stay. - **Neighborhood:** Windsor City Centre - **Nearby attractions:** Thames Path - 0.2 km, St. Georges Chapel - 0.1 km, Theatre Royal - 0.2 km ## Top Windsor Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - [Hotels with Tennis Courts in Ascot ](https://www.expedia.ca/Ascot-Hotels-Hotels-With-Tennis-Courts.0-0-d4271-tHotelswithTennisCourts.Travel-Guide-Filter-Hotels) - [Spa Hotels in Ascot ](https://www.expedia.ca/Ascot-Hotels-Spa-Hotel.0-0-d4271-tSpaHotel.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in Brunel ](https://www.expedia.ca/Brunel-London-Hotels-LGBT-Friendly-Hotel.0-n553248635976383089-0-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [B&B in Datchet ](https://www.expedia.ca/Datchet-Bed-And-Breakfast.d601766-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Datchet Hotels ](https://www.expedia.ca/Datchet-Hotels.d601766.Travel-Guide-Hotels) - 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