Windsor Vacations from $384

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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
Price was $423, price is now $384 per person
$384
per person
Nov 28 - Nov 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Windsor (YQG)
9.2/10 Wonderful! (84 reviews)
This comfortable B&B was perfect. The hospitality was above and beyond, as were the delicious breakfasts cooked for us. I would definitely recommend it if staying in the Leamington area.

Reviewed on Oct 5, 2025

Caesars Windsor

Caesars Windsor

4 out of 5
City Centre
Price was $1,618, price is now $1,459 per person
$1,459
per person
Nov 14 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Dublin (DUB) to Windsor (YQG)
8.6/10 Excellent! (3,058 reviews)
Not able to use either this trip

Reviewed on Oct 8, 2025

Travelodge by Wyndham Windsor

Travelodge by Wyndham Windsor

2 out of 5
Devonshire
Price was $1,253, price is now $1,146 per person
$1,146
per person
Nov 14 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Dublin (DUB) to Windsor (YQG)
7/10 Good! (1,008 reviews)
The bathroom needs to have an upgrade on the toilet to a higher type toilet and the Shower needs to be upgraded with a wand type. The continental breakfast was very good and beverages were very good. Staff was friendly and helpful.

Reviewed on Oct 6, 2025

Parkside Flat #5 - Seacliff Beach Suites

Parkside Flat #5 - Seacliff Beach Suites

4 out of 5
Price was $503, price is now $460 per person
$460
per person
Nov 28 - Nov 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Windsor (YQG)
10/10 Exceptional! (3 reviews)
Windsor Manor

Windsor Manor

4 out of 5
City Centre
Price was $1,296, price is now $1,190 per person
$1,190
per person
Nov 14 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Dublin (DUB) to Windsor (YQG)
No reviews
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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

4.5/5(68 reviews)

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

4.5/5(4 reviews)

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

Roasting Experience at 14th Coffee Co

Roasting Experience at 14th Coffee Co

$69
per adult
Roasting Experience at 14th Coffee Co
Downtown Detroit Donut and Pastry Adventure

Downtown Detroit Donut and Pastry Adventure

$70
per adult
Downtown Detroit Donut and Pastry Adventure
Step into the shadows and discover the haunting tales of Motor City's past.

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

$32
per adult
Motor City Ghosts: Haunts, Spirits, and Poltergeists Walking Tour
See all activities in Windsor

Windsor Hotel Deals

Caesars Windsor

Caesars Windsor

4 out of 5
377 Riverside Dr E, Windsor, ON
$126 nightly
The price is $151 total per night from Oct 20 to Oct 21
$151 total
Oct 20 - Oct 21
Total with taxes and fees
8.6/10 Excellent! (3,070 reviews)
"Not able to use either this trip"

Reviewed on Oct 8, 2025

Caesars Windsor
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
$82 nightly
The price is $98 total per night from Nov 2 to Nov 3
$98 total
Nov 2 - Nov 3
Total with taxes and fees
8/10 Very Good! (1,000 reviews)
"Front desk staff were welcoming. An brekkie included in the price would have been nice."

Reviewed on Oct 7, 2025

Best Western Plus Waterfront Hotel
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
$108 nightly
The price is $130 total per night from Oct 12 to Oct 13
$130 total
Oct 12 - Oct 13
Total with taxes and fees
8.6/10 Excellent! (1,332 reviews)
"Room was good. Parking should be included with they stay. Was disappointed that I had to payextra for parking. This is the first ti.e that I had to pay for parking ontop off the room. I would consider staying else where for my next visit."

Reviewed on Oct 4, 2025

Holiday Inn Express Windsor Waterfront by IHG
See all 389 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.

Windsor Essential Information

Language
English
Currency
Canadian dollars
Closest Airport
Windsor Airport (YQG)
Population
278,000
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Adventure Bay Family Water Park, Chrysler Theatre and Walkerville Brewery

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Frequently asked questions

How much does a Windsor vacation package cost?
You'll find cheap prices from $384 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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