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
$67 nightly
The price is $73 total per night from Apr 15 to Apr 16
$73 total
Apr 15 - Apr 16
Total with taxes and fees
9/10 Wonderful! (99 reviews)
Everything was great!

Reviewed on Apr 5, 2026

Windsor Crossroads Motel
Parkfield Inn

Parkfield Inn

2.5 out of 5
506 Kansas Ave Clinton MO
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $119 total per night from Apr 16 to Apr 17
$119 total
Apr 16 - Apr 17
Total with taxes and fees
9.2/10 Wonderful! (1,003 reviews)
Very clean nice breakfast.

Reviewed on Apr 11, 2026

Parkfield 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
$84 nightly
The price is $95 total per night from Apr 20 to Apr 21
$95 total
Apr 20 - Apr 21
Total with taxes and fees
8/10 Very Good! (753 reviews)
Very little hot water available. Continental breakfast was good. Rooms were clean with adequate parking. Just was disappointed with the hot water situation. I haved stayed several times over the past few years. First time wth hot h2o ussue.

Reviewed on Apr 12, 2026

Westbridge Inn and Suites
See all 205 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.