Windsor Holidays

Book a Hotel + Flight or Car together to unlock savings

    deals illustration
    Better together
    Save up to £335 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

Windsor Essential Information

Language
English
Currency
U.S dollars
Population
2,800
Max Temp Winter
4ºC
Max Temp Summer
29ºC

Our pick of the best Windsor Hotel Deals

Windsor Crossroads Motel
Windsor Crossroads Motel
2.5 out of 5
606 North Main Street, Windsor, MO
Stay at this motel in Windsor. Enjoy free parking, daily housekeeping and a picnic area.
9/10 Wonderful! (80 reviews)
"Simple clean and quiet"

Reviewed on 18 Jun 2025

Windsor Crossroads Motel
Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO
Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO
Windsor, MO
Stay at this holiday home in Windsor. Enjoy laundry facilities, an in-room coffee maker and air conditioning.
9.4/10 Exceptional! (30 reviews)
small
"House is small but nice. The stairs going upstairs have a fold down ladder attic access and bit tricky to climb up."

Reviewed on 12 Feb 2025

Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO
Econo Lodge Truman Inn
Econo Lodge Truman Inn
2 out of 5
3501 W Broadway Blvd, Sedalia, MO
Stay at this business-friendly hotel in Sedalia. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Daum Museum of Contemporary Art and Missouri ...
5.6/10 (670 reviews)
"Staff was very friendly and responded quickly to one issue with the bathroom lock."

Reviewed on 8 Jun 2025

Econo Lodge Truman Inn
See all 192 properties in Windsor
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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Windsor travel package cost?
Our Windsor packages, which start from just , are the best way to save loads of cash. Choose your preferred flights, hotels and rental cars to create a customized getaway.
If I'm not able to travel, can I cancel my Windsor travel package?
It's good to know that you can cancel your Windsor booking if your travel plans have changed. Whether you'll be charged a fee or not depends on your hotel, airline or car rental company. You may be able to cancel or change your booking for free if you booked in the last 24 hours. Head to our Customer Service Portal for more information.
How do I get a cheap travel package to Windsor?
Creating your own Windsor holiday package with Expedia is a great way to save. We have over 550 partner airlines and 1,000,000 properties across the globe. With such an amazing range to select from, you'll have no hassles pulling together your perfect trip.
Does Expedia offer Book Now, Pay Later Windsor holidays?
Expedia has partnered with online lender Klarna to make booking your next getaway easier on your hip pocket. Paying by instalment means you can spread the costs of your dream holiday, leaving you with more money to play with while you're travelling. Klarna has several payment plans to choose from, so you're sure to find one that works with your budget. Browse these flexible payment options:

  • Pay monthly holidays: If paying bite-sized amounts each month works for you, Klarna can help. Paying in easy monthly instalments will make your holiday dreams possible.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it possible to pay for your trip across multiple transactions.
  • Low deposit holidays: Hitting the "book now" button is easier with this plan. Just put down a small deposit on your booking and then start packing your bags.

Where should I stay in Windsor?
A getaway in Windsor isn't complete without seeing Royal Oaks Hospital. Why not book a hotel close to this fantastic attraction?
What are the top hotels in Windsor?
Pear Tree Inn St. Louis Airport and City Place St. Louis Downtown are two of the most sought-after hotels in Windsor. Why not check out the rates and amenities at each and then make a decision?
How far in advance should I book my Windsor holiday?
Travellers are normally able to browse international flights on Expedia within 12 months of the departure date. Booking late? With a bit of luck, it's still possible to score an affordable ticket just weeks before your journey.
What does an Expedia Windsor travel package include?
Hotels, flights and a reliable car for your road trip adventures. Simply select your favourite bundle and get access to incredible deals. Once you've made your booking, add on some sightseeing tours and watch your savings pile up. When it comes to creating your Windsor holiday, you're in control!
What should I know before booking a Windsor travel package?
When you book your flights, hotels and car rentals together, you'll nab awesome discounts. Whether you're organising an island getaway in a villa or want to stay in a luxurious city hotel, Expedia will help make it happen.
Can I choose my airline with a Windsor Expedia travel package?
Yes --- that's one of the best things about an Expedia travel package. You can mix and match your flights, hotels and more. We have access to more than 550 partner airlines worldwide, so you have options galore when arranging your Windsor getaway.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.