Windsor Vacations

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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
$70 nightly
The price is $76 total per night from Nov 26 to Nov 27
$76 total
Nov 26 - Nov 27
Total with taxes and fees
9/10 Wonderful! (96 reviews)
Very clean, newly renovated and the manager was so helpful, even to offer to help us get supplies for our continuing bike trip. thenks

Reviewed on Oct 27, 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
$180 nightly
The price is $189 total per night from Nov 26 to Nov 27
$189 total
Nov 26 - Nov 27
Total with taxes and fees
9.4/10 Exceptional! (31 reviews)
Perfect stop right on the Katy Trail! All was just as described in the listing. Close to shopping areas to stock up on food and supplies. Sent stay request on Friday after 6pm to arrive on Saturday and host replied within an hour that late reservation was no problem and property would be ready for ...

Reviewed on Sep 29, 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
$78 nightly
The price is $88 total per night from Dec 11 to Dec 12
$88 total
Dec 11 - Dec 12
Total with taxes and fees
8/10 Very Good! (709 reviews)
Everything was nice

Reviewed on Nov 14, 2025

Westbridge Inn and Suites
See all 197 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

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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.