
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
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
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
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
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
Windsor Hotel Deals

Vacation Village in the Berkshires
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

Berkshire Mountain Lodge
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

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