Windsor Vacations

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Find the Best Windsor Vacation Packages

Windsor Hotel Deals

The Lodge at Geneva
The Lodge at Geneva
3.5 out of 5
4888 N. Broadway, Geneva, OH
Fully refundableReserve now, pay when you stay
The price is AED 584 per night from Apr 13 to Apr 14
AED 584
AED 725 total
includes taxes & fees
13 Apr - 14 Apr
9.2/10 Wonderful! (652 reviews)
"Beautiful views! Rooms were very clean. I didn't like the strong air freshoner smell in the main lobby. I would strongly suggest staying here!"

Reviewed on 31 March 2025

The Lodge at Geneva
Red Roof Inn Cleveland - Mentor/ Willoughby
Red Roof Inn Cleveland - Mentor/ Willoughby
2 out of 5
4166 State Route 306, Willoughby, OH
Fully refundableReserve now, pay when you stay
The price is AED 241 per night from Apr 13 to Apr 14
AED 241
AED 277 total
includes taxes & fees
13 Apr - 14 Apr
7.4/10 Good! (975 reviews)
"Staff is great and makes me feel at home everytime, appreciate all the efforts made to make my stay possible whenever I’m there! Another great say!!"

Reviewed on 4 April 2025

Red Roof Inn Cleveland - Mentor/ Willoughby
Red Roof Inn Ashtabula - Austinburg
Red Roof Inn Ashtabula - Austinburg
2 out of 5
1860 Austinburg-Ashtabula Rd, I-90 Exit 223, Austinburg, OH
Fully refundableReserve now, pay when you stay
The price is AED 231 per night from Apr 15 to Apr 16
AED 231
AED 266 total
includes taxes & fees
15 Apr - 16 Apr
6.6/10 (706 reviews)
"I come in from Arizona several times a year because of proximity to my son. The staff are always very friendly and helpful, but my last 2 stays (January and now) i have been VERY disappointed at the cleanliness of the rooms. Both times there was hair, dirt and dust bunnies on the bathroom floor, ..."

Reviewed on 25 March 2025

Red Roof Inn Ashtabula - Austinburg
See all 491 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 pleasantly surprised at how much a vacation to Windsor costs! Expedia’s packages make travel planning easier and your savings go further.
What are the cheapest months to go to Windsor?
If you’re hoping to score a cheap Windsor vacation package, consider planning a trip in January, February and November. You’re likely to find lower rates on flights and accommodations during these months — ideal for a budget-friendly break.
How to find the best Windsor package deals?
Use Expedia’s filters to help you find some tempting Windsor package deals. When you start your search, just set your maximum budget and then order the results by “Price: low to high.” If you want to save, plan your break for midweek, or browse for Windsor package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it’s usually best to lock in your vacation package well in advance.
Is it cheaper to book a Windsor vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You’ll typically land a better deal than booking each component separately. And you’ll still get the flexibility to create a tailored Windsor vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Windsor?
Secure incredible discounts by booking your flights early with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Windsor break.
How to plan a trip to Windsor?

  1. Choose when to go: Check your schedule and pack your bags. Your favorite time of year and the type of activities on offer will also help you decide when to escape to Windsor.
  2. Set a budget: Factor in costs like flights, meals and transportation when working out how much to put aside for your trip to Windsor. Then, pick a property that fits your budget, whether that’s a wallet-friendly stay or a swankier getaway.
  3. Decide how long to go away for: Now that you’re more familiar with Windsor, you can figure out the ideal length of your break. Pull together a draft plan and give yourself enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a tailored Windsor vacation package.

Discover the most popular places to visit in Windsor

Windsor Mills Covered Bridge

5/5(3 reviews)

Learn about the local history of Windsor when you take a trip to Windsor Mills Covered Bridge. Experience the area's festivals and entertainment venues.

Windsor Mills Covered Bridge