Windsor Holidays

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Top hotels in Windsor

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 €68 per night from 3 Dec to 4 Dec
€68
3 Dec - 4 Dec
includes taxes & fees
Windsor Crossroads Motel
Parkfield Inn

Parkfield Inn

2.5 out of 5
506 Kansas Ave Clinton MO
Fully refundableReserve now, pay when you stay
The price is €118 per night from 8 Nov to 9 Nov
€118
8 Nov - 9 Nov
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"Place is a decently quiet and clean hotel. Limited options in Clinton. Basic but good"

Reviewed on 5 Nov 2026

Parkfield Inn
Econo Lodge Truman Inn

Econo Lodge Truman Inn

2 out of 5
3501 W Broadway Blvd Sedalia MO
Fully refundableReserve now, pay when you stay
The price is €71 per night from 1 Dec to 2 Dec
€71
1 Dec - 2 Dec
includes taxes & fees
5.8/10 (878 reviews)
"If you want to save money, stay here. If you want to be right by Walmart an a couple restaurants , stay here . For the price you save don't except all the extras . The pool is not heated. The Jacuzzi could've been hotter. Some of the things that you might be used to they do not have . No coffee pot ..."

Reviewed on 3 Nov 2026

Econo Lodge Truman Inn
See all 236 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 holiday package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a holiday 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 holiday packages and you could get some excellent off-season deals.
How many days is enough for Windsor?
With a well-organised schedule, you can easily hit the main Windsor attractions in a few days. But if you want to discover hidden gems or go on day trips, consider booking your Windsor holiday for longer.
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," "Traveller 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 holiday as a package?
An Expedia holiday 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 holiday 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 favourite 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 accommodation 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 holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.