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.
Berkshire Mountain Lodge
Price was CA $632, price is now CA $524 per person
CA $524
per person
Aug 31 - Sep 3
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9/10 Wonderful! (980 reviews)
Property very well maintained, everything you would need for an extended stay, we stayed one night for a show at Tanglewood(20” away) The rooms have microwave, fridge, dishes, dishwasher,etc. everything you would need to eat in. Also pool, hot tub, exercise and movies at night in a great room. Helpful staff, great price for a great room( separate dining area, living area, bedroom and huge bathroom!!!!!) extra clean woukd def go back
Reviewed on Jun 21, 2026
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Price was CA $743, price is now CA $621 per person
CA $621
per person
Aug 31 - Sep 3
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (910 reviews)
Mini golf was amazing, as was having access to shuffleboard, cornhole and more. And the arcade was great, too, we went back many times! Room was clean and nice with it's own balcony and the resort was calm and quiet.
Reviewed on Jun 19, 2026
Best Western Plus Berkshire Hills Inn & Suites
Price was CA $634, price is now CA $545 per person
CA $545
per person
Aug 31 - Sep 3
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
8.6/10 Excellent! (1,001 reviews)
The towels and bedding were very nice and the bed was comfortable. There was ample, close parking. However, the sink drain was slow. There was no body wash in the shower. The refrigerator noise was so loud we had to unplug it while we slept. The breakfast was poor (no fruit or meat) and the eggs & biscuits and gravy were barely warm. I would not recommend this hotel.
Reviewed on Jun 17, 2026
The Yankee Inn
Price was CA $693, price is now CA $597 per person
CA $597
per person
Aug 31 - Sep 3
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (1,016 reviews)
I had an excellent experience with the Yankee Inn. The room was updated and the house keeping was excellent. The location was good and the staff was very nice. The breakfast was very good. I would definitely recommend staying here.
Reviewed on Jun 23, 2026
Windsor Hotel Deals
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
The price is CA $215 per night from Jun 30 to Jul 1
CA $215
CA $240 total
Jun 30 - Jul 1
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
"No real breakfast"
Reviewed on Jun 21, 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
The price is CA $203 per night from Jul 7 to Jul 8
CA $203
CA $226 total
Jul 7 - Jul 8
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
"I had an excellent experience with the Yankee Inn. The room was updated and the house keeping was excellent. The location was good and the staff was very nice. The breakfast was very good. I would definitely recommend staying here."
Reviewed on Jun 23, 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
The price is CA $165 per night from Jul 12 to Jul 13
CA $165
CA $200 total
Jul 12 - Jul 13
includes taxes & fees
8.8/10 Excellent! (2,408 reviews)
"very scenic and well maintained property"
Reviewed on Jun 23, 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.
