
Windsor Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to CA $1,096 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
Windsor Hotel Deals

Windsor Crossroads Motel
606 North Main Street, Windsor, MO
Fully refundableReserve now, pay when you stay
The price is CA $97 per night from Aug 21 to Aug 22
CA $97
CA $105 total
Aug 21 - Aug 22
includes taxes & fees
9/10 Wonderful! (84 reviews)
"Soooo clean! Room was small but very comfortable. We slept well. Nice mattress."
Reviewed on Aug. 15, 2025

Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO
Windsor
The price is CA $137 per night from Aug 21 to Aug 22
CA $137
CA $215 total
Aug 21 - Aug 22
includes taxes & fees
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

Westbridge Inn and Suites
106 S Baird St., Clinton, MO
Fully refundableReserve now, pay when you stay
The price is CA $104 per night from Aug 24 to Aug 25
CA $104
CA $123 total
Aug 24 - Aug 25
includes taxes & fees
8/10 Very Good! (655 reviews)
"Clean complex. Older motel but well kept. Friendly staff"
Reviewed on Aug. 19, 2025
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
Other vacations you might like
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
Expedia's Latest Trends
Hotels
Flights
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.