Windsor Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now

Windsor Hotel Deals

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
$180 nightly
The price is $194 total per night from Feb 28 to Mar 1
$194 total
Feb 28 - Mar 1
Total with taxes and fees
Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO
Windsor Crossroads Motel

Windsor Crossroads Motel

2.5 out of 5
606 North Main Street Windsor MO
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $76 total per night from Feb 28 to Mar 1
$76 total
Feb 28 - Mar 1
Total with taxes and fees
9/10 Wonderful! (97 reviews)
Room was very cold even with heater going on 80. Had to ask for towels as well as was double charged on a night which was told was prior authorization and it still took 79 off my card additional. Will not be returning.

Reviewed on Feb 2, 2026

Windsor Crossroads Motel
Comfort Inn Sedalia Station

Comfort Inn Sedalia Station

2.5 out of 5
3600 W Broadway Blvd Sedalia MO
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $120 total per night from Mar 29 to Mar 30
$120 total
Mar 29 - Mar 30
Total with taxes and fees
9.2/10 Wonderful! (607 reviews)
room was very clean and the staff was very nice

Reviewed on Feb 15, 2026

Comfort Inn Sedalia Station
See all 202 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.

Find the Best Windsor Vacation Packages

Windsor Essential Information

Language
English
Currency
U.S dollars
Population
2,800

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

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're likely to find lower rates and greater availability in December, January and February. Take a look at our cheap Windsor vacation packages and you could get some great off-season deals.
How many days is enough for Windsor?
Typically, a handful of days is enough to go to the major sights during your Windsor vacation. But if you'd like to have more time to chill out or go on day trips, think about extending your itinerary.
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.
Does Expedia offer Book Now, Pay Later Windsor vacation packages?
Your Windsor trip is meant to be a relaxing escape from your busy life, not a reason for money-related stress. So to give you a little more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.