Windsor Vacation Packages
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Your Windsor Vacation
Enjoy amazing adventures when you reserve a Windsor vacation package. Whether you're a history buff, foodie or just a traveler who loves discovering new places, there's something for everyone in this awesome city. If seeing the sights is a priority during your trip to Windsor, make sure you swing by popular attractions like Wahconah Falls State Park and Bas Ridge Golf Course. No matter your travel plans or the size of your budget, organizing a tailored Windsor vacation is a walk in the park with Expedia.
Top Windsor Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Albany Airport Inn
CA $712
per person
Oct 16 - Oct 19
found 9 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
6.6/10 (1,005 reviews)
Great staff! Checked in and returned my rental car. I called the hotel after dropping off the car and they sent the shuttle to pick me up within minutes and dropped me off at the door number closest to my room. Room can be updated a little bit.. not by much though.
Reviewed on Aug 12, 2026
Hampton Inn & Suites Albany-Downtown
Downtown Albany
CA $874
per person
Oct 16 - Oct 19
found 9 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
8.8/10 Excellent! (1,058 reviews)
The hotel was very busy and only one elevator worked. There were stains on the mattress pad visible under the thin sheets. The breakfast was minimal. The parking situation was not explained well ($20/night) Place has potential to be much better
Reviewed on Aug 9, 2026
Hilton Albany
Downtown Albany
CA $861
per person
Oct 16 - Oct 19
found 9 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
7.4/10 Good! (1,154 reviews)
It’s in a good location. Staff at front desk are rigid & unfriendly. AC did not work throughout an entire weekend long dance completion event. Mouse ran through the women’s Hair/Make-up room. Bathtub in room didn’t drain when shower was used. Nice restaurant & bar staff and food was fairly good. I would not stay again.
Reviewed on Aug 12, 2026
Fairfield Inn & Suites by Marriott Albany Downtown
Downtown Albany
CA $939
per person
Oct 16 - Oct 19
found 9 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
8.6/10 Excellent! (1,002 reviews)
The room was ok, pretty basic, but the A/C did not work - it was 78° in the room, and the bathroom sink drain was stopped up with hair that had never been cleaned. The staff was friendly enough and the breakfast was about what you would expect.
Reviewed on Aug 10, 2026
Ready to book your vacation to Windsor?
Windsor Hotel Deals
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
CA $135
CA $166 total
Sep 2 - Sep 3
includes taxes & fees
8.8/10 Excellent! (2,521 reviews)
"Pool and staff was great"
Reviewed on Aug 12, 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
CA $207
CA $231 total
Sep 7 - Sep 8
includes taxes & fees
9.2/10 Wonderful! (1,023 reviews)
"The room was clean. Linens in good shape. Good access to lots of activities nearby. Breakfast can be crowded. Go early."
Reviewed on Aug 11, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
CA $132
CA $178 total
Aug 31 - Sep 1
includes taxes & fees
9/10 Wonderful! (1,063 reviews)
"!st floor is horrible and host would not switch us to a higher floor. Our room was near the laundry room, and you could hear the staff every morning, when rooms above would flush their toilets you could hear the water through the walls, very annoying through the night, Couch in the room had tears ..."
Reviewed on Aug 12, 2026
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 $712 on Expedia, you'll be pleasantly surprised at how much a vacation to Windsor costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Windsor?
You can typically find lower prices and greater availability in January, February and March. Explore our cheap Windsor vacation packages and you could land some great off-season discounts.
How many days is enough for Windsor?
With a well-organized itinerary, you can easily tick off the top Windsor attractions in a handful of days. But if you want to discover hidden gems or go on 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 preferred trip dates and destination under our "Packages" tab. Then add a few filters, like "Popular locations" and "Property type," 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 ideal Windsor package deal straight away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Windsor adventure off to a flying start.
Is it cheaper to book a Windsor vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and stays individually. Better still, you can personalize your Windsor trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Windsor?
If you've got your Windsor travel dates locked in, book as early as you can to grab some unbeatable deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Windsor?
- Choose when to go: Check your diary and get packing. Your favourite time of year and the activities on offer will also help you decide when to visit Windsor.
- Work out your budget: Make sure you have enough money to cover everything from transportation and dining out to flights and activities. Your accommodations will probably be the largest expense during your trip to Windsor.
- Decide how long to go away for: Now that you're more familiar with Windsor, you can figure out the ideal length of your break. Create a rough plan and allocate enough time to cover everything you want to see.
- Combine your hotel and flights: Epic destination, check. Length of stay, check. Now 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.
