Windsor Vacations

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    Save up to AEDĀ 5,000 when you book a flight and hotel together*

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Find the Best Windsor Vacation Packages

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 AEDĀ 257 per night from Jul 24 to Jul 25
AEDĀ 257
AEDĀ 279 total
24 Jul - 25 Jul
includes taxes & fees
Windsor Crossroads Motel
Econo Lodge Truman Inn

Econo Lodge Truman Inn

2 out of 5
3501 W Broadway Blvd Sedalia MO
Fully refundable
The price is AEDĀ 286 per night from Jul 27 to Jul 28
AEDĀ 286
AEDĀ 325 total
27 Jul - 28 Jul
includes taxes & fees
5.8/10 (819 reviews)
"Room was sufficiently clean, staff as ok, parking was available, bed was comfortable. Room needed some updating, Cot that was provided was very uncomfortable. No internet, minimal tv options. Room smelled musty/cigarette like."

Reviewed on 13 July 2026

Econo Lodge Truman Inn
Parkfield Inn

Parkfield Inn

2.5 out of 5
506 Kansas Ave Clinton MO
Get rates
Parkfield Inn
See all 216 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?
You can pick up a vacation package to this destination on Expedia. But how much your vacation to Windsor costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Windsor?
January, March and October are the best times to look for cheap Windsor vacation packages. Opting to travel in quieter months means you'll typically find better prices on flights and hotels.
How to find the best Windsor package deals?
Use Expedia's filters to find some terrific Windsor package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Windsor package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Windsor vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component separately. And you'll still get the flexibility to create a personalized Windsor vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Windsor?
If you're considering a spontaneous Windsor getaway, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Windsor?

  1. Choose your travel dates: What you want to do in Windsor and your preferred season can help you decide when to go.
  2. Figure out your budget: Make sure you have enough money to pay for everything from meals and transportation to activities and airfares. Your accommodations will likely be the biggest expense during your trip to Windsor.
  3. Decide how many days away: Start by making a list of all the attractions you'd like to experience in Windsor. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose a Windsor vacation package that brings all your bookings together.