Windsor Vacations from $309
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The Latest Windsor vacation packages
Price found within the past 48 hours. Click for updated prices.
Silver Heart Inn and Cottages
$387
per person
Oct 21 - Oct 24
found 13 hours ago
Roundtrip flight included
Denver (DEN) to Kansas City (MCI)
9.6/10 Exceptional! (124 reviews)
The Hotel Silver Heart Inn was an amazing place to stay....beautifully maintained 170 year old home decorated with wonderful antiques. Breakfast was served in the morning including fresh fruit, german apple pancake and sausage! We loved the touches including bathrobes, and Gentle Bee shampoo, conditioner, body wash and lotion. The Gentle Bee was so amazing I ordered shampoo and conditioner when I got home! We would 100% stay at Silver Heart Inn again!!
Reviewed on Sep 4, 2026
The Inn at Meadowbrook
$827
per person
Nov 14 - Nov 17
found 19 hours ago
Roundtrip flight included
Philadelphia (PHL) to Kansas City (MCI)
9.8/10 Exceptional! (448 reviews)
The Inn at Meadowbrook was a lovely experience. It’s a clean and spacious property with exceptional staff. The Verbena restaurant on site is particularly good, patronised by guests and locals. One amenity I really enjoyed was the “Bevi” water dispenser on each floor, complete with an ice machine. Still or sparkling water with a choice of flavours was on tap. This was really appreciated as Kansas was experiencing extreme heat at the time.
Reviewed on Sep 5, 2026
Windsor Hotel Deals
Windsor Crossroads Motel
606 North Main Street Windsor MO
Fully refundableReserve now, pay when you stay
$70 nightly
$76 total
Sep 7 - Sep 8
Total with taxes and fees
9.2/10 Wonderful! (109 reviews)
"Great place to stay. Friendly and professional staff. Clean rooms."
Reviewed on Aug 24, 2026
Econo Lodge Truman Inn
3501 W Broadway Blvd Sedalia MO
$78 nightly
$89 total
Sep 8 - Sep 9
Total with taxes and fees
Westbridge Inn and Suites
106 S Baird St. Clinton MO
Fully refundableReserve now, pay when you stay
$87 nightly
$98 total
Oct 6 - Oct 7
Total with taxes and fees
8/10 Very Good! (834 reviews)
"The property was clean on the grounds and in the office. Rooms were clean and comfortable. The bathroom was clean and the water was hot. The television did not work. The room had a very strong smell of air freshener. It was a very strong smell - too strong really. There is an ice maker near the office. ..."
Reviewed on Sep 5, 2026
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 from $309 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.