A rustic barn surrounded by autumn foliage and a field.

Windsor Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Your Windsor Vacation

The cosmopolitan vibe and rich history are just the beginning of the things Windsor has going for it. Enjoy the best parts of this fascinating city your way with a personalized Windsor vacation package. A trip to Windsor is an ideal opportunity to see the sights. Be sure to stop by big-name attractions such as XL Center, Xfinity Theatre and University of Hartford. Whatever your travel plans or budget, putting together the ultimate tailored Windsor vacation is simple with Expedia.

Top Windsor vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Jan 21 - Jan 23

    The Surfside Hotel + Flight

    Lordship
    2 nights
    2.0 star property
    9.2/10 - Wonderful (229 reviews)
    Roundtrip • Toronto (YYZ) - New Haven (HVN)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $698
    CA $667
    per traveller
    found 1 day ago
    The Surfside Hotel
  • Dec 13 - Dec 16

    Beechmont - Perfect for Family Retreat! + Flight

    North End
    3 nights
    5.0 star property
    Roundtrip • Toronto (YYZ) - New Haven (HVN)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $2,035
    CA $1,779
    per traveller
    found 1 day ago
    Beechmont - Perfect for Family Retreat!

Discover the most popular places to visit in Windsor

What to do in Windsor

Windsor Hotel Deals

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 from CA $667 on Expedia, you'll be surprised at how little a vacation to Windsor costs! Our packages mean less travel planning for you and greater savings.

What are the cheapest months to go to Windsor?

If you're looking to score a cheap Windsor vacation package, consider planning a trip in December, January and February. You'll generally find lower rates on flights and hotels during these months — perfect for travellers wishing to save money.

How many days is enough for Windsor?

With about 2 days, you'll have enough time to enjoy popular neighbourhoods such as Downtown Hartford and North Meadows during your Windsor vacation. Make sure to also add Shoppes at Buckland Hills and Promenade Shops at Evergreen Walk to your must-see list. Looking for more adventures? Consider venturing outside of Windsor on day trips and tours.

Is it worth booking a vacation package to Windsor?

Whether you're looking to explore attractions such as Oliver Ellsworth Homestead and Windsor Meadows State Park on your Windsor vacation, or coming for its excellent history, festivals and culture, there's something for everyone here. With so much to see and do, you'll soon discover why so many people think Windsor is a good vacation destination.

How to find the best Windsor package deals?

Finding a cheap Windsor package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, add a couple of filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most economical Windsor package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.

Is it cheaper to book a Windsor vacation as a package?

Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Windsor vacation by choosing your favourite type of stay, airline and car class.

When to book a vacation package to Windsor?

If you're considering a spontaneous Windsor adventure, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can score incredible deals on your hotels and flights by booking ahead.

How to plan a trip to Windsor?

  1. Choose when to travel: Check your diary and get your bags packed. Your favourite 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 expenses like flights, meals and transportation when working out how much to put aside for your trip to Windsor. Then, choose a hotel that fits your budget, whether that's a wallet-friendly option or a more upscale getaway.
  3. Decide how long to go away for: Now that you know more about Windsor, you can work out the perfect length of your break. Put together a rough itinerary and give yourself enough time to get through everything on your must-do list.
  4. Bundle your airfare and accommodations: After you've nailed down your trip dates and duration, lock in the ideal Windsor vacation package for you.

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