
Windsor Vacation Packages
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Save up to CA $1,096 when you book a flight and hotel together*
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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.

Hampton Inn & Suites Manchester-Bedford
Price was CA $1,175, price is now CA $1,080 per person
CA $1,080
per person
Oct 3 - Oct 6
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Manchester (MHT)
8.4/10 Very Good! (1,003 reviews)
The beds were comfortable
Carpeting in the halls were dirty
Reviewed on Aug. 17, 2025



Four Points by Sheraton Bedford Manchester Airport
Price was CA $1,301, price is now CA $1,179 per person
CA $1,179
per person
Oct 3 - Oct 6
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Manchester (MHT)
8.8/10 Excellent! (84 reviews)
Great room for the price, microwave and refrigerator and Netflix plus other streaming options. Very nice accommodations!!!
Reviewed on Aug. 14, 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 $174 per night from Aug 28 to Aug 29
CA $174
CA $188 total
Aug 28 - Aug 29
includes taxes & fees
8.4/10 Very Good! (881 reviews)
"Had a great time at this location"
Reviewed on Aug. 19, 2025

Days Inn by Wyndham Keene NH
3 Ash Brook Road, Keene, NH
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Sep 1 to Sep 2
CA $154
CA $168 total
Sep 1 - Sep 2
includes taxes & fees
7/10 Good! (1,002 reviews)
"Would stay again"
Reviewed on Aug. 16, 2025

Best Western Plus Keene Hotel
401 Winchester St, Keene, NH
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from Aug 24 to Aug 25
CA $207
CA $224 total
Aug 24 - Aug 25
includes taxes & fees
8.2/10 Very Good! (1,012 reviews)
"Clean, comfortable room, great breakfast & friendly staff."
Reviewed on Aug. 17, 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.
Frequently asked questions
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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.