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.
Super 8 by Wyndham Albany

Super 8 by Wyndham Albany

2 out of 5
per person
Oct 11 - Oct 18
found 1 hour ago
Roundtrip non-stop flight included
Edmonton (YEG) to Albany (ALB)
6.8/10 (1,006 reviews)
Every time I stay here, I have a different experience. This was the third distinct room I've experienced. I think we got a free upgrade, from a queen to a king. What we got was a time capsule. The left side was reasonable. An old suite. Clean and appealing. The right side... where the old, unusable jacuzzi remains and a bathroom that, unlike all the other rooms I've stayed in there, needs serious renovations. Again, all other rooms have renovated bathrooms. Even the handle of the water in the shower came off. A different experience. This will be a great room should it ever be renovated.

Reviewed on Jul. 27, 2025

DoubleTree by Hilton Schenectady Downtown

DoubleTree by Hilton Schenectady Downtown

4 out of 5
Seward Place
per person
Oct 11 - Oct 18
found 1 hour ago
Roundtrip non-stop flight included
Edmonton (YEG) to Albany (ALB)
8.4/10 Very Good! (669 reviews)
enjoyed the sunday farmers market which was within walking distance. recommend Ambition Coffee for breakfast.

Reviewed on Jul. 27, 2025

Hampton Inn Schenectady Downtown

Hampton Inn Schenectady Downtown

2.5 out of 5
Seward Place
per person
Oct 11 - Oct 18
found 1 hour ago
Roundtrip non-stop flight included
Edmonton (YEG) to Albany (ALB)
9/10 Wonderful! (940 reviews)
Our stay was very good. All staff were very helpful and friendly. The food was great and at breakfast the staff were very friendly and helpful. Our room was very clean, and our beds were very comfortable. We enjoyed our stay.

Reviewed on Jul. 30, 2025

La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area

La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area

3 out of 5
per person
Oct 11 - Oct 18
found 1 hour ago
Roundtrip non-stop flight included
Edmonton (YEG) to Albany (ALB)
8.8/10 Excellent! (1,002 reviews)
The breakfast was great. The ladies kept the eggs coming out and the coffee was brewed to perfection. The staff were very knowledgeable; (they explained they couldn't take my AARP for a discount; I had to use it while I was booking our room. Also explained why they charged for our daughter, who is 16, again had to show when booking, everyone had a smile Our daughter & her cousin enjoyed the hot tub. The rooms, bathrooms were clean and well stocked with towels.

Reviewed on Aug. 5, 2025

Hilton Garden Inn Albany Airport

Hilton Garden Inn Albany Airport

3 out of 5
per person
Oct 11 - Oct 18
found 1 hour ago
Roundtrip non-stop flight included
Edmonton (YEG) to Albany (ALB)
8/10 Very Good! (1,168 reviews)
You can stay there and leave your car when you fly

Reviewed on Aug. 2, 2025

Ready to book your vacation to Windsor?

 

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Windsor Hotel Deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is CA $126 per night from Aug 27 to Aug 28
CA $126
CA $156 total
Aug 27 - Aug 28
includes taxes & fees
8.6/10 Excellent! (1,923 reviews)
"The unit has everything you need and is very clean. It would benefit from a step stool in the kitchen area because you can't reach the dishes without standing on a chair. Also it says you MUST use a convention pan to use the cooktop but there isn't one. Parking is difficult -- the spaces area too ..."

Reviewed on Aug. 3, 2025

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is CA $152 per night from Aug 24 to Aug 25
CA $152
CA $201 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (537 reviews)
"Great location to stay between Tanglewood concerts. Will come again."

Reviewed on Aug. 2, 2025

Berkshire Mountain Lodge
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is CA $98 per night from Aug 6 to Aug 7
CA $98
CA $109 total
Aug 6 - Aug 7
includes taxes & fees
5.2/10 (758 reviews)
"Will stay at again."

Reviewed on Aug. 1, 2025

FairBridge Inn Express
See all 976 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?
Offering great value package deals from CA $809 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.