Windsor Vacation Packages

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Your Windsor Vacation

When you book a vacation package to Windsor, you can relax and enjoy your getaway knowing that all your travel arrangements are under control. Discover the many delights of this vibrant city from your base in a neighborhood like Princeton Meadows, which is great for golfing. During your trip to Windsor, carve some time in your schedule for sightseeing. A popular place to begin exploring is Working Dog Winery. Whoever you're escaping with and whatever you plan to spend, your dream Windsor vacation is just a few clicks away with Expedia.

Top Windsor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Jersey City on the Hudson

Hyatt Regency Jersey City on the Hudson

4 out of 5
Downtown Jersey City
Save 100% on your flight
per person
Aug 28 - Sep 1
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.2/10 Very Good! (1,429 reviews)
Great location! Friendly staff and very clean.

Reviewed on Jul. 6, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8.4/10 Very Good! (532 reviews)
Right on the water. Private beach with chair and umbrellas.they will serve you right on the beach bye getting you food and drinks also has a outdoor swimming pool..nice staff..nothing special about the continental breakfast..bagels, fruit, small croissants, small danish and some hard boiled eggs..coffee and oj..i was pleased with my stay. King deluxe room..small table with chairs on the shared deck..could sit outside til about 2pm and the sun starts to beat on you but no biggy..was very humid out when my wife and i was there..a/ c really could not cool the room as much as we would have liked. Nothing wrong with the a/c it just because the sun beating on the hotel all day..luckily i brought a couple of small usb fans to help keep cool at night while we slept did the trick..overall i enjoy my stay and you could not ask for anything more when it comes to the scenery..

Reviewed on Jul. 10, 2025

Dream Downtown, by Hyatt

Dream Downtown, by Hyatt

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.8/10 Good! (1,475 reviews)
Can’t wait to come back!!!

Reviewed on Jul. 15, 2025

The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
Save 100% on your flight
per person
Sep 2 - Sep 6
found 5 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to New York (JFK)
8.8/10 Excellent! (480 reviews)
Location and view - unbeatable !!

Reviewed on Jul. 15, 2025

Empire Hotel

Empire Hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
Sep 22 - Sep 25
found 11 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
7.6/10 Good! (5,584 reviews)
Will stay here every time. Good quality and reasonable price. PERFECT for the Lincoln Centre!

Reviewed on Jul. 15, 2025

Ready to book your vacation to Windsor?

 

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Windsor Hotel Deals

Hilton East Brunswick Hotel & Executive Meeting Center

Hilton East Brunswick Hotel & Executive Meeting Center

3.5 out of 5
3 Tower Center Blvd, East Brunswick, NJ
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Jul 23 to Jul 24
CA $150
CA $172 total
Jul 23 - Jul 24
includes taxes & fees
7.2/10 Good! (1,013 reviews)
Good hotel, shaky service.
"Hotel was very busy the weekend of our stay. Our room was a little later than the 4 pm check in. One staff member was of no help, but another went out of her way to get us in as quickly as possible, while offering us bottled water while we waited. Overall, I thought the hotel was clean and modern ..."

Reviewed on Jul. 14, 2025

Hilton East Brunswick Hotel & Executive Meeting Center
Hyatt Regency Princeton

Hyatt Regency Princeton

4 out of 5
102 Carnegie Ctr, Princeton, NJ
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from Aug 16 to Aug 17
CA $207
CA $238 total
Aug 16 - Aug 17
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Very nice room."

Reviewed on Jul. 15, 2025

Hyatt Regency Princeton
MHO Hotel Bordentown

MHO Hotel Bordentown

2 out of 5
187 US 130 and 206, Bordentown, NJ
Fully refundableReserve now, pay when you stay
The price is CA $88 per night from Jul 17 to Jul 18
CA $88
CA $101 total
Jul 17 - Jul 18
includes taxes & fees
7.8/10 Good! (1,001 reviews)
"I just sleep here"

Reviewed on Jul. 16, 2025

MHO Hotel Bordentown
See all 426 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Windsor vacation package cost?
Offering great value package deals from CA $767 on Expedia, you'll be surprised at how little a vacation to Windsor costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Windsor?
January, February and March are great times to look for cheap Windsor vacation packages. Choosing to travel in less busy months means you can generally find better prices on flights and accommodations.
How many days is enough for Windsor?
With a well-organized travel plan, you can easily tick off the top Windsor sights in a few days. But if you'd like to venture off the beaten track or take day trips, think about booking your Windsor vacation for longer.
How to find the best Windsor package deals?
Begin your search for a Windsor package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Windsor package deal right away, just tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Windsor adventure underway.
Is it cheaper to book a Windsor vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and accommodations individually. Better still, you can tailor your Windsor trip to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Windsor?
If you have your Windsor travel dates finalized, book as early as you can to grab some outstanding deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for travelling on a whim.
How to plan a trip to Windsor?

  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Windsor.
  2. Budget wisely: Besides the price of your accommodations, you should factor in other expenses. These include transportation, flights and food. Also, put aside some extra funds for unexpected costs that could arise during your trip to Windsor.
  3. Decide how long to go for: Now that you know more about Windsor, you can work out the right length of your break. Put together a rough itinerary and allocate enough time to cover everything you want to do.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to find a Windsor vacation package that brings all your bookings together.

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