
Windsor Vacation Packages
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Your Windsor Vacation
Our vacation packages to Windsor provide endless opportunities to delve into new sights, sounds and smells. And with all of the travel arrangements taken care of, you can kick back and enjoy your city escape to the fullest. Eager to do a little sightseeing? Spend your days enjoying popular attractions such as Franklin Pierce Homestead during your trip to Windsor. No matter your travel plans or budget, putting together a tailored Windsor vacation is easy with Expedia.
Top Windsor Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Mountain Lodge at Okemo
Clock Tower Base Area
per person
Oct 17 - Oct 22
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8/10 Very Good! (207 reviews)
Loved the location for this ski in ski out. Nice to look out the balcony and be right in the middle of the action. The sofa bed was uncomfortable with springs popping up all over. The back door didn't lock and the window handle was broken . There was a light bulb that was out and not all the outlets worked. The tv situation was a nightmare with one tv all snowy and the other one whose remote was missing the select button and could not choose a channel. The location was great but would not choose this room again .
Reviewed on Feb. 19, 2025

The Shire Woodstock
per person
Oct 17 - Oct 22
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.8/10 Excellent! (791 reviews)
The Air Conditioning unit was waking me up every time it started up. Room 225. That is my only inconvenience. Everything else was wonderful.
Reviewed on Aug. 1, 2025

Jackson Gore Village
Jackson Gore Base Area
per person
Oct 17 - Oct 22
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.6/10 Excellent! (738 reviews)
The property itself was nice. The restaurant was good, a little overpriced for quality but still pretty good. The bed wasnt the most comfortable but also ok. Our room didnt have a mini fridge, which made it hard to buy and store the delicious cheeses you cam purchase at all the neighboring cheese factories and dairy farms. There was enough things to do in the area for a few summer days. The pool was large and clean. They also had a bunch of hot tubs, which was nice.
Reviewed on Aug. 4, 2025


Mount Snow Grand Summit Resort
per person
Oct 17 - Oct 22
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.8/10 Excellent! (209 reviews)
The staff was excellent!
The room was clean but terrible! The king size bed was as hard as a rock!! Got very little sleep. The room had sings of water damage in the corner by the window. The TV is in a strange spot to watch from the bed and the cable nut was tripped and would not tighten down. The bathroom door would not shut unless you forced it closed. The shower head leaked unless you turned it off very hard. There was no night stand on one side of the bed making one person putting there stuff on the floor next to the bad. On top of all of this there was an extra $25.00 dollar fee witch I was not expecting for the room. The resort was excellent though and the staff was great. I heated the room!
Reviewed on Aug. 1, 2025
Windsor Hotel Deals

Keene Elm City Hotel, Ascend Hotel Collection
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from Aug 13 to Aug 14
CA $172
CA $187 total
Aug 13 - Aug 14
includes taxes & fees
8.4/10 Very Good! (871 reviews)
"Is a very well cared for hotel and I enjoyed my stay and I’ve stayed there several times."
Reviewed on Aug. 5, 2025

Best Western Plus Keene Hotel
401 Winchester St, Keene, NH
Fully refundableReserve now, pay when you stay
The price is CA $195 per night from Aug 24 to Aug 25
CA $195
CA $212 total
Aug 24 - Aug 25
includes taxes & fees
8.2/10 Very Good! (1,005 reviews)
"Great place!"
Reviewed on Jul. 31, 2025

Courtyard by Marriott Keene Downtown
75 Railroad St, Keene, NH
Fully refundableReserve now, pay when you stay
The price is CA $260 per night from Aug 7 to Aug 8
CA $260
CA $282 total
Aug 7 - Aug 8
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Property in good condition, clean, well located in Keene."
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.