Windsor Vacations from $431

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The Latest Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
Hawthorne Inn

Hawthorne Inn

2 out of 5
Price was $439, price is now $431 per person
$431
per person
Nov 7 - Nov 9
found 17 hours ago
Roundtrip flight included
Chicago (ORD) to Versailles (VRS)
9.2/10 Wonderful! (46 reviews)
A beautiful home with a history. Very clean and well kept. A wonderful home cooked breakfast. I would definitely recommend.

Reviewed on Feb 26, 2025

Lazy Dayz Resort

Lazy Dayz Resort

3 out of 5
Price was $702, price is now $566 per person
$566
per person
Oct 7 - Oct 12
found 13 hours ago
Roundtrip flight included
Chicago (ORD) to Versailles (VRS)
8.6/10 Excellent! (24 reviews)
Arrived and was given literally zero direction on getting into our cabin, expectations or process of needs for the week. First night we spent the evening at Boondockz and had a freaking blast with the locals. Drinks were great and there was plenty of things for the kids 12& over to do. The rest of the week we had a heck of a time catching anyone in the office for things needed. The cabin…. There is so much potential for this cabin but man the whole place needs some TLC. I loved the cabin but to hold 12 like the ad said is a joke. Not enough bed space, towels, seating in the living room and literally NOTHING for cooking in the tiny kitchen. We ended up spending around $50 at DG for things we needed just to make it the week. Would we stay here again, no, but it does have the potential to be a great fun place that could be very enjoyable by a bigger family like ours.

Reviewed on Jul 25, 2025

Panoramic Paradise - Lakefront Home for 15

Panoramic Paradise - Lakefront Home for 15

4.5 out of 5
Price was $2,237, price is now $2,128 per person
$2,128
per person
Oct 7 - Oct 12
found 13 hours ago
Roundtrip flight included
Chicago (ORD) to Versailles (VRS)
No reviews
Sunset Escape - Fit For 8

Sunset Escape - Fit For 8

4 out of 5
Price was $677, price is now $660 per person
$660
per person
Oct 7 - Oct 12
found 13 hours ago
Roundtrip flight included
Chicago (ORD) to Versailles (VRS)
No reviews
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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 Aug 26 to Aug 27
$76 total
Aug 26 - Aug 27
Total with taxes and fees
9/10 Wonderful! (85 reviews)
"there was nothing about the property I didnt like"

Reviewed on Aug 21, 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
9.4/10 Exceptional! (30 reviews)
small
"House is small but nice. The stairs going upstairs have a fold down ladder attic access and bit tricky to climb up."

Reviewed on Feb 12, 2025

Get rates
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
$72 nightly
The price is $81 total per night from Aug 26 to Aug 27
$81 total
Aug 26 - Aug 27
Total with taxes and fees
8/10 Very Good! (655 reviews)
"Clean complex. Older motel but well kept. Friendly staff"

Reviewed on Aug 19, 2025

Westbridge Inn and Suites
See all 189 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.

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Frequently asked questions

How much does a Windsor vacation package cost?
Offering great value package deals from $431 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.