Windsor Vacation Packages
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Your Windsor Vacation
The cosmopolitan vibe and rich history are just the beginning of the things Windsor has going for it. Enjoy the best parts of this fascinating city your way with a personalized Windsor vacation package. A trip to Windsor is an ideal opportunity to see the sights. Be sure to stop by big-name attractions such as XL Center, Xfinity Theatre and University of Hartford. Whatever your travel plans or budget, putting together the ultimate tailored Windsor vacation is simple with Expedia.
Top Windsor Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Liberty Inn
Price was CA $686, price is now CA $645 per person
CA $645
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
7.6/10 Good! (645 reviews)
I'll start off with the positives:
- The greeter, who I presume was the owner, was kind and allowed me to start my check-in early (with a fee, but that was to be expected).
- The property, despite having the layout of a motel, looked very nice. And the moment I stepped into my room, it felt I was in a high-class hotel.
- Most (not all, but I'll get to that in the negatives) amenities were provided.
- The price, compared to what else I was finding in the area, was relatively inexpensive.
And now for the negatives:
- A very minor one, but tissues would be a nice amenity to have had in the room.
- The location is close to the highway. Probably great for finding business from weary travelers, but unideal for morning-sleepers like I.
- The chairs in the room, though looking nice, felt cheaply made. I heard the one I sat at cracking as I sat, and I feared it might break underneath me.
Reviewed on Apr 27, 2026
Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
Price was CA $908, price is now CA $739 per person
CA $739
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
8/10 Very Good! (1,002 reviews)
Parking was easy. Bed mattress terrible. Tired room and furnishings. Basic supplies.
Reviewed on Apr 28, 2026
Madison Beach Hotel
Madison Center
Price was CA $2,065, price is now CA $1,776 per person
CA $1,776
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
9.4/10 Exceptional! (367 reviews)
Excellent hotel, high quality in every way, beautiful setting, very quiet relaxing and peaceful Sunday night stay off-season.
Reviewed on Apr 28, 2026
Tower Inn And Suites Of Guilford - Madison
Price was CA $805, price is now CA $792 per person
CA $792
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
7.4/10 Good! (243 reviews)
It was great. Easy check in and check out. Love that the chexk out qas at 11 and noe wicked early. If i go to a event in the area again i would definitely stay here again.
Reviewed on May 4, 2026
Windsor Hotel Deals
Marriott Hartford/Windsor Airport
28 Day Hill Rd Windsor CT
Fully refundableReserve now, pay when you stay
The price is CA $272 per night from May 17 to May 18
CA $272
CA $313 total
May 17 - May 18
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
Over priced for everything.,did not have a shuttle ready for me, and there were to many kids this past weekend.. So a lot of noise going on all night. Hotel had no control. Room above me was banging all night . It was not a peaceful stay definitely not worth what I paid! Never again
Reviewed on May 4, 2026
Residence Inn by Marriott Hartford/Windsor
100 Dunfey Ln Windsor CT
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from May 25 to May 26
CA $163
CA $187 total
May 25 - May 26
includes taxes & fees
8.2/10 Very Good! (748 reviews)
This was a very pleasant experience. I travel often for work and personal. The grounds look like a townhouse or condo development. Staff was accommodating, room was clean, well kept like a nice studio apartment. Full breakfast basic but good. The only things concerning was the room was on the second ...
Reviewed on May 3, 2026
HYATT house Hartford North/Windsor
200 Corporate Dr Windsor CT
Fully refundableReserve now, pay when you stay
The price is CA $205 per night from May 26 to May 27
CA $205
CA $236 total
May 26 - May 27
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
J'aurais aimé un meilleur.entretien quotidien de la.chambre, sinon le tout était parfait
Reviewed on May 1, 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.
Discover the most popular places to visit in Windsor
Windsor Historical Society
You can spend an afternoon browsing the exhibits at Windsor Historical Society during your trip to Windsor. Experience the great live music or attend a sporting event in this family-friendly area.
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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.
