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.
Hampton Inn Hartford/Airport
Price was CA $792, price is now CA $678 per person
CA $678
per person
Oct 17 - Oct 19
found 3 hours ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
9/10 Wonderful! (1,005 reviews)
I always wipe down the surfaces in my room. They were clean. 😀 The housekeeper Nidia? was very, very nice.
Reviewed on Aug. 29, 2025
James Pharmacy Bed & Breakfast
Old Saybrook Center
Price was CA $2,346, price is now CA $1,911 per person
CA $1,911
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to New Haven (HVN)
9.4/10 Exceptional! (16 reviews)
We loved the convenient location and beautiful historic building, but we were very disappointed in the level of cleanliness (a layer of dust on shelves and fireplace, cobwebs under furniture). There were some other issues (loose shower head, broken coffee maker). There's no one on site to address in person. It's a lovely place, but needs some attention. For the price, it should be better! :(
Reviewed on May 1, 2025
Microtel Inn & Suites by Wyndham Uncasville Casino Area
Price was CA $1,634, price is now CA $1,356 per person
CA $1,356
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to New Haven (HVN)
8.8/10 Excellent! (1,742 reviews)
Convenient, spacious clean rooms, friendly staff.
Reviewed on Aug. 31, 2025
Saybrook Point Resort & Marina
Old Saybrook Center
Price was CA $1,590, price is now CA $1,335 per person
CA $1,335
per person
Oct 10 - Oct 13
found 8 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to New Haven (HVN)
9.4/10 Exceptional! (1,006 reviews)
Great place couldn’t even take my financeé away from the pool even if god asked her to leave
Reviewed on Aug. 29, 2025
The Bevin House Bed & Breakfast
Price was CA $785, price is now CA $683 per person
CA $683
per person
Oct 17 - Oct 19
found 3 hours ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
9.6/10 Exceptional! (78 reviews)
The staff was super friendly and welcoming. The house was beautiful and the grounds full of things to explore. The breakfast was presently with panache and tasted great. We swam in the pool, ate at local restaurants, pet a turkey, and visited the local winery. I would highly recommend this establishment.
Reviewed on Aug. 8, 2025
Windsor Hotel Deals
Marriott Hartford/Windsor Airport
28 Day Hill Rd, Windsor, CT
Fully refundableReserve now, pay when you stay
The price is CA $232 per night from Sep 5 to Sep 6
CA $232
CA $267 total
Sep 5 - Sep 6
includes taxes & fees
HYATT house Hartford North/Windsor
200 Corporate Dr, Windsor, CT
Fully refundableReserve now, pay when you stay
The price is CA $218 per night from Sep 1 to Sep 2
CA $218
CA $251 total
Sep 1 - Sep 2
includes taxes & fees
Hilton Garden Inn Hartford North/Bradley Int'l Airport
555 Corporate Dr, Windsor, CT
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from Sep 3 to Sep 4
CA $186
CA $214 total
Sep 3 - Sep 4
includes taxes & fees
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.