Windsor Vacations

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Find the Best Windsor Vacation Packages

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
The price is AED 239 per night from Mar 24 to Mar 25
AED 239
AED 260 total
includes taxes & fees
24 Mar - 25 Mar
9/10 Wonderful! (76 reviews)
"Very pleasant stay. Most definitely would recommend. Easy to get around as well"

Reviewed on 23 February 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
The price is AED 364 per night from Mar 30 to Mar 31
AED 364
AED 573 total
includes taxes & fees
30 Mar - 31 Mar
9.4/10 Exceptional! (28 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 12 February 2025

Newly remodeled, cozy cottage only steps away from the Katy Trail in Windsor, MO
Parkfield Inn
Parkfield Inn
2.5 out of 5
506 Kansas Ave, Clinton, MO
Fully refundableReserve now, pay when you stay
The price is AED 393 per night from Mar 24 to Mar 25
AED 393
AED 443 total
includes taxes & fees
24 Mar - 25 Mar
9/10 Wonderful! (855 reviews)
"Friendly, helpful staff. A little bit of an older place. Location is good. There are some stores and a couple of places to eat. Pool is good."

Reviewed on 17 March 2025

Parkfield Inn
See all 184 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.

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 can typically find reduced prices and greater availability in January, March and October. Explore our cheap Windsor vacation packages and you could get some excellent off-season deals.
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.
How to plan a trip to Windsor?

  1. Choose when to get away: Check your diary and pack your bags. Your favorite season and the available activities will also help you decide when to visit Windsor.
  2. Figure out your budget: Make sure you have enough money to cover everything from transportation and dining out to flights and experiences. Your accommodations will probably be the largest expense during your trip to Windsor.
  3. Set the duration of your trip: Start by making a list of all the sights and activities you’d like to experience in Windsor. Then, estimate how long you’ll need for each, including any travel time.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that’s left is to find a Windsor vacation package that brings all your bookings together.