Windsor Vacations from $1,442

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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.
Nicklin House

Nicklin House

3 out of 5
per person
Sep 17 - Sep 21
found 13 hours ago
Roundtrip flight included
Amman (AMM) to Windsor (YQG)
9.2/10 Wonderful! (66 reviews)
This was the most amazing bed and breakfast I’ve ever stayed at . The room was beautiful and everything was laid out for us. Most enjoyable stay we’ve ever had ! Paul makes an absolutely astonishing breakfast Outside property was perfectly set up for guests and socializing I highly recommend that anyone stays in this area to book a room here .

Reviewed on Jul 21, 2025

Parkside Flat #5 - Seacliff Beach Suites

Parkside Flat #5 - Seacliff Beach Suites

4 out of 5
per person
Sep 17 - Sep 21
found 13 hours ago
Roundtrip flight included
Amman (AMM) to Windsor (YQG)
10/10 Exceptional! (3 reviews)
Caesars Windsor

Caesars Windsor

4 out of 5
City Centre
per person
Sep 17 - Sep 21
found 13 hours ago
Roundtrip flight included
Amman (AMM) to Windsor (YQG)
8.6/10 Excellent! (3,024 reviews)
We enjoyed our stay. Everyone was friendly and helpful. It was quite a walk to get to the reception desk. Having to walk through the casino and find the reception desk wasn't fun.

Reviewed on Jul 30, 2025

Park Bungalow #4 - Seacliff Beach Suites

Park Bungalow #4 - Seacliff Beach Suites

3 out of 5
per person
Sep 17 - Sep 21
found 13 hours ago
Roundtrip flight included
Amman (AMM) to Windsor (YQG)
9.4/10 Exceptional! (11 reviews)
The property is super clean. Walking distance to the parks. Gas stations, groceries shopping are all closed by.

Reviewed on Jul 28, 2025

Coastal #1 and Cozy #2 - Seacliff Beach Suites

Coastal #1 and Cozy #2 - Seacliff Beach Suites

3.5 out of 5
per person
Sep 17 - Sep 21
found 13 hours ago
Roundtrip flight included
Amman (AMM) to Windsor (YQG)
9.8/10 Exceptional! (8 reviews)
Thanks for a lovely stay! The property and room was clean and well-equipped, and the views are beautiful! We appreciated the easy check in, and loved the gazebo. We’ll definitely rebook the next time we’re in the area.

Reviewed on Mar 15, 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 vibrant 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 entertainment choices 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

Downtown Detroit Donut and Pastry Adventure

Downtown Detroit Donut and Pastry Adventure

$70
per adult
Downtown Detroit Donut and Pastry Adventure
Roasting Experience at 14th Coffee Co

Roasting Experience at 14th Coffee Co

$69
per adult
Roasting Experience at 14th Coffee Co
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
See all activities in Windsor

Windsor Hotel Deals

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
$118 nightly
The price is $141 total per night from Aug 10 to Aug 11
$141 total
Aug 10 - Aug 11
Total includes taxes and fees
8/10 Very Good! (1,004 reviews)
Nice but hot
"Very friendly, nice. Beautiful view of Detroit!. Except for the air conditioning not working with little help. Only offer was to change rooms at 1am"

Reviewed on Jul 27, 2025

Best Western Plus Waterfront Hotel
Caesars Windsor

Caesars Windsor

4 out of 5
377 Riverside Dr E, Windsor, ON
$125 nightly
The price is $149 total per night from Sep 1 to Sep 2
$149 total
Sep 1 - Sep 2
Total includes taxes and fees
8.4/10 Very Good! (3,025 reviews)
"We enjoyed our stay. Everyone was friendly and helpful. It was quite a walk to get to the reception desk. Having to walk through the casino and find the reception desk wasn't fun."

Reviewed on Jul 30, 2025

Caesars Windsor
DoubleTree by Hilton Windsor Hotel & Suites

DoubleTree by Hilton Windsor Hotel & Suites

4 out of 5
333 Riverside Dr W, Windsor, ON
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $142 total per night from Aug 10 to Aug 11
$142 total
Aug 10 - Aug 11
Total includes taxes and fees
9/10 Wonderful! (1,005 reviews)
"It was a decent property to stay at but we had been spoiled in other hotels that earned a bit higher of a rating. The cookies however were delicious."

Reviewed on Jul 31, 2025

DoubleTree by Hilton Windsor Hotel & Suites
See all 374 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 $1,442 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.