Windsor Trips (flight + hotel)

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    Better together
    Save up to P 3,118 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Windsor

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 P3,676 per night from Jun 30 to Jul 1
P3,676
P3,996 total
Jun 30 - Jul 1
includes taxes & fees
9/10 Wonderful! (80 reviews)
"Simple clean and quiet"

Reviewed on Jun 18, 2025

Windsor Crossroads Motel
Econo Lodge Truman Inn
Econo Lodge Truman Inn
2 out of 5
3501 W Broadway Blvd, Sedalia, MO
Fully refundableReserve now, pay when you stay
The price is P4,242 per night from Jul 6 to Jul 7
P4,242
P4,965 total
Jul 6 - Jul 7
includes taxes & fees
5.6/10 (669 reviews)
"Staff was very friendly and responded quickly to one issue with the bathroom lock."

Reviewed on Jun 8, 2025

Econo Lodge Truman Inn
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 P4,327 per night from Jun 30 to Jul 1
P4,327
P5,090 total
Jun 30 - Jul 1
includes taxes & fees
8/10 Very Good! (625 reviews)
"Excellent! Safe, Clean, Friendly! Would stay again definitely."

Reviewed on Jun 26, 2025

Westbridge Inn and Suites
See all 186 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.

Frequently asked questions

How much does a Windsor vacation package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a vacation 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 vacation packages and you could get some excellent off-season deals.
How many days is enough for Windsor?
With a well-organized 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 vacation 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," "Traveler 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 vacation as a package?
An Expedia vacation 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 vacation 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 favorite 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 accommodations 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 vacation 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.