Windsor Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to AU$703 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Windsor Holiday

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
Fully refundableReserve now, pay when you stay
The price is AU$118 per night from 21 Aug to 22 Aug
AU$118
21 Aug - 22 Aug
includes taxes & fees
9/10 Wonderful! (84 reviews)
"Soooo clean! Room was small but very comfortable. We slept well. Nice mattress."

Reviewed on 15 Aug. 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
The price is AU$245 per night from 21 Aug to 22 Aug
AU$245
21 Aug - 22 Aug
includes taxes & fees
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
Westbridge Inn and Suites

Westbridge Inn and Suites

2 out of 5
106 S Baird St., Clinton, MO
Fully refundableReserve now, pay when you stay
The price is AU$135 per night from 24 Aug to 25 Aug
AU$135
24 Aug - 25 Aug
includes taxes & fees
8/10 Very Good! (653 reviews)
"Very nice place would definitely stay again"

Reviewed on 17 Aug. 2025

Westbridge Inn and Suites
See all 189 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
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Windsor holiday package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a holiday to Windsor costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Windsor?
You can typically find reduced prices and greater availability in January, March and October. Explore our cheap Windsor holiday packages and you could get some excellent off-season deals.
How many days is enough for Windsor?
With a well-organised schedule, you can easily hit the main Windsor attractions in a few days. But if you want to discover hidden gems or go on day trips, consider booking your Windsor holiday for longer.
How to find the best Windsor package deals?
Bagging a cheap Windsor package deal is easy with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget range, add a few filters and see what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to view the most wallet-friendly Windsor package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Windsor holiday as a package?
An Expedia holiday package could land you considerable savings when compared to booking flights and hotels separately. Better still, you can tailor your Windsor escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a holiday package to Windsor?
If you're considering a spontaneous Windsor trip, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land incredible deals on your hotels and flights by booking well in advance.
How to plan a trip to Windsor?

  1. Choose when to get away: Check your diary and pack your bags. Your favourite season and the available activities will also help you decide when to visit Windsor.
  2. Figure out your budget: Make sure you have enough money to cover everything from transportation and dining out to flights and experiences. Your accommodation will probably be the largest expense during your trip to Windsor.
  3. Set the duration of your trip: Start by making a list of all the sights and activities you'd like to experience in Windsor. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to find a Windsor holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.