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.
Hampton Inn & Suites Albany-Downtown
Downtown Albany
Price was CA $1,348, price is now CA $1,159 per person
CA $1,159
per person
Jul 10 - Jul 15
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.8/10 Excellent! (1,057 reviews)
We had to switch rooms due to a leaking shower. Somehow it was leaking into the room. Additionally the shower was “handicap” accessible but also sprayed water all over the bathroom floor. However they immediately moved us upon complaint.
Reviewed on Apr 20, 2026
Hampton Inn Albany-Wolf Road (Airport)
Price was CA $1,391, price is now CA $1,178 per person
CA $1,178
per person
Jul 10 - Jul 15
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.8/10 Excellent! (1,010 reviews)
Staff was great. Bathrooms could use a little upkeep.
Reviewed on May 1, 2026
Best Western Plus Franklin Square Inn Troy/Albany
Price was CA $1,500, price is now CA $1,290 per person
CA $1,290
per person
Jul 10 - Jul 15
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.8/10 Excellent! (1,009 reviews)
Parking was safe
Had to leave before breakfast
Reviewed on Apr 27, 2026
Hyatt Place Albany/Downtown
Downtown Albany
Price was CA $1,454, price is now CA $1,259 per person
CA $1,259
per person
Jul 10 - Jul 15
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9/10 Wonderful! (1,599 reviews)
Amazing stay! No issues, I would definitely stay again!
Reviewed on May 7, 2026
Windsor Hotel Deals
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is CA $120 per night from May 24 to May 25
CA $120
CA $164 total
May 24 - May 25
includes taxes & fees
9/10 Wonderful! (925 reviews)
Room very spacious and clean. Full kitchen is a great bonus.
Reviewed on May 4, 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is CA $155 per night from May 14 to May 15
CA $155
CA $173 total
May 14 - May 15
includes taxes & fees
9/10 Wonderful! (932 reviews)
Easy, comfortable and convenient; rooms and public spaces are nice, modern and stylish updates of modest 60s/70s original motel facilities.
Reviewed on May 6, 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from May 12 to May 13
CA $118
CA $147 total
May 12 - May 13
includes taxes & fees
8.8/10 Excellent! (2,351 reviews)
I loved my stay at the resort! The view was beautiful, my room was clean, and the staff were nice. I had trouble with my door, and they sent someone quickly to fix it.
Reviewed on May 8, 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.
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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.
