Windsor Vacations from $1,569

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Your Windsor Vacation

When you book a vacation package to Windsor, all the organizing is taken care of beforehand. This gives you more time to discover some of the best things about this riverfront city, such as its cosmopolitan vibe, diversity and friendly locals. You'll want to sightsee during your trip to Windsor. Carve out some time for big-name attractions such as Detroit Windsor Tunnel, Caesars Casino and Caesars Windsor. Expedia is here to help you escape your routine. Tailor your vacation to Windsor to suit your travel style, whatever that may look like.

The Latest Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites by Hilton Windsor

Hampton Inn & Suites by Hilton Windsor

2.5 out of 5
South Cameron
Price was $1,576, price is now $1,569 per person
$1,569
per person
Sep 28 - Sep 29
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to Windsor (YQG)
8.6/10 Excellent! (1,006 reviews)
Everything was good, would definitely stay again. Good breakfast selection, plenty of options.

Reviewed on Aug 22, 2025

Caesars Windsor

Caesars Windsor

4 out of 5
City Centre
Price was $1,609, price is now $1,595 per person
$1,595
per person
Sep 28 - Sep 29
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to Windsor (YQG)
8.6/10 Excellent! (3,043 reviews)
You have to go through the casino to get to your room.

Reviewed on Aug 22, 2025

Hotel STRY

Hotel STRY

2 out of 5
Price was $1,629, price is now $1,618 per person
$1,618
per person
Sep 28 - Sep 29
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to Windsor (YQG)
10/10 Exceptional! (11 reviews)
What an amazing hotel. It feels like we're staying at someone's well designed home. My daughter LOVES the bunk beds and I like that they're in a separate cubby-like area. There were welcome treats left to enjoy. And the surrounding neighborhood offers a number of shops, restaurants, and coffee shops. What a great getaway!

Reviewed on Aug 5, 2025

Windsor Manor

Windsor Manor

4 out of 5
City Centre
Price was $1,632, price is now $1,622 per person
$1,622
per person
Sep 28 - Sep 29
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to Windsor (YQG)
No reviews
Sandwich Boutique Hotel

Sandwich Boutique Hotel

3 out of 5
Sandwich
Price was $1,592, price is now $1,585 per person
$1,585
per person
Sep 28 - Sep 29
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to Windsor (YQG)
9.2/10 Wonderful! (17 reviews)
Well set up with a common kitchen area, basic room and bathroom. Everything one needs. Location was very convenient. Host was very approachable, even though not on site, and responded very quickly to questions.

Reviewed on Jun 12, 2025

Don't see what you're looking for?
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Where to stay in Windsor

Find the best Windsor areas and neighborhoods for the activities you enjoy most. Learn more about Windsor
Windsor featuring signage

Downtown Windsor

4 out of top 10 points of interest in this area

If you're spending some time in Downtown Windsor, Detroit Windsor Tunnel and Chrysler Theatre are top sights worth seeing.

Find hotels in Downtown Windsor

Discover the most popular places to visit in Windsor

Detroit is making a come back and you should see all it has to offer. Take a day to walk down town and the river front. You may be pleasantly surprise by what you see and feel about the motor city. From River days, to the American Auto show, to all the many events at Cobo hall and DTE center Detroit wants to welcome tourists and explorers. https://midlifemilestones.com/downtown-detroit/

Caesars Casino

Why not try your luck with a visit to Caesars Casino during your time in Windsor? Discover the top-notch restaurants and acclaimed theater scene in this family-friendly area.

Caesars Casino
Ambassador Bridge

Ambassador Bridge

You can learn about the history of Windsor with a visit to Ambassador Bridge. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.

Ambassador Bridge
Windsor Riverfront showing a sunset, a river or creek and fishing

Windsor Riverfront

After visiting Windsor Riverfront, make a plan to see the other sights and activities in Windsor.

Windsor Riverfront

What to do in Windsor

Step into the shadows and discover the haunting tales of Motor City's past.

Motor City Ghosts: Haunts, Spirits, and Poltergeists Walking Tour

$26
per adult
Motor City Ghosts: Haunts, Spirits, and Poltergeists Walking Tour
Downtown Detroit Donut and Pastry Adventure

Downtown Detroit Donut and Pastry Adventure

$70
per adult
Downtown Detroit Donut and Pastry Adventure
Detroit: Architectural Beauty and Hidden Gems Walking Tour

Detroit: Architectural Beauty and Hidden Gems Walking Tour

$135
per adult
Detroit: Architectural Beauty and Hidden Gems Walking Tour
See all activities in Windsor

Windsor Hotel Deals

Caesars Windsor

Caesars Windsor

4 out of 5
377 Riverside Dr E, Windsor, ON
$124 nightly
The price is $149 total per night from Sep 1 to Sep 2
$149 total
Sep 1 - Sep 2
Total with taxes and fees
8.4/10 Very Good! (3,031 reviews)
"I loved this hotel!! Everything was excellent!!! The staff, the restaurants (Spago for supper and Johnny Rockets for breakfast), the room (super comfortable bed and pillows)!! The casino itself was so clean! I definitely will be going back to this hotel!!!"

Reviewed on Aug 20, 2025

Caesars Windsor
Holiday Inn Express Windsor Waterfront by IHG

Holiday Inn Express Windsor Waterfront by IHG

2.5 out of 5
33 Riverside Drive East, Windsor, ON
Fully refundable
$104 nightly
The price is $124 total per night from Sep 1 to Sep 2
$124 total
Sep 1 - Sep 2
Total with taxes and fees
8.6/10 Excellent! (1,299 reviews)
"La proximité les service a la clientelle excellent"

Reviewed on Aug 20, 2025

Holiday Inn Express Windsor Waterfront by IHG
Best Western Plus Waterfront Hotel

Best Western Plus Waterfront Hotel

2.5 out of 5
277 Riverside Drive West, Windsor, ON
Fully refundableReserve now, pay when you stay
$117 nightly
The price is $141 total per night from Aug 25 to Aug 26
$141 total
Aug 25 - Aug 26
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
"Appreciated the river front view, all else good"

Reviewed on Aug 20, 2025

Best Western Plus Waterfront Hotel
See all 387 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.

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Frequently asked questions

How much does a Windsor vacation package cost?
You'll find cheap prices from $1,569 on Expedia for your Windsor getaway. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Windsor costs.
What are the cheapest months to go to Windsor?
If you're looking to snag a cheap Windsor vacation package, consider planning a trip in December, January and February. You'll usually find lower prices on airfares and hotels during these months — perfect for travelers wishing to save money.
How many days is enough for Windsor?
Windsor vacations come in various shapes and sizes, but to really sink your teeth into this place, we'd say 2 days is a good ballpark. This will mean you can fit in headline attractions like Walkerville Brewery and Windsor Community Museum and seek out some underrated gems. Don't miss out on neighborhoods such as Sandwich Towne and South Central either. If you plan wisely, you can even allow for a day trip from Windsor too.
Is it worth booking a vacation package to Windsor?
Windsor has everything you need for an amazing escape. Begin your Windsor vacation on a high note by visiting popular attractions like Adventure Bay Family Water Park.
How to find the best Windsor package deals?
Landing a cheap Windsor package deal is easy with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Windsor package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Windsor vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component individually. And you'll still have the freedom to create a customized Windsor vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Windsor?
If you're considering a spontaneous Windsor getaway, 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 find awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Windsor?

  1. Choose when to go: Check your schedule and get packing. Your favorite season and the activities on offer will also help you decide when to visit Windsor.
  2. Set your budget: Factor in expenses such as food, flights and transportation when calculating how much to put aside for your trip to Windsor. Then, choose a hotel that fits your budget, whether that's a low-cost stay or a deluxe getaway.
  3. Explore Windsor with Expedia's trip planning tool: Gain insights into the top attractions and best hotels for your trip to Windsor. You can also save your must-visit places, collaborate with friends and family and organize all your plans in one place.
  4. Decide your trip length: Think about how long you want to spend exploring Windsor. Plan your days so you can get to all the activities and attractions you're interested in at a leisurely pace.
  5. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to find a Windsor vacation package that brings all your bookings together.
  6. Book activities and experiences in advance: Whether it's entrance to a big attraction or a walking tour, you won't have to worry about missing out on the highlights of Windsor. Find all the fun things to do in Windsor with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Windsor vacation packages?
If you're anything like us, you love traveling the world but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Windsor vacation across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.