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.
Super 8 by Wyndham Old Saybrook

Super 8 by Wyndham Old Saybrook

2 out of 5
Price was CA $816, price is now CA $737 per person
CA $737
per person
Jul 30 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
7/10 Good! (925 reviews)
The office was not open when we got there had to keep ringing the buzzer when we left in the morning there was no one in the office.

Reviewed on Jun 14, 2026

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was CA $1,092, price is now CA $889 per person
CA $889
per person
Jul 30 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8/10 Very good! (1,000 reviews)
Convenient, very outdated

Reviewed on Jun 22, 2026

Liberty Inn

Liberty Inn

2 out of 5
Price was CA $846, price is now CA $803 per person
CA $803
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to New Haven (HVN)
7.6/10 Good! (651 reviews)
Clean convenient place, reasonably priced

Reviewed on Jun 4, 2026

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
Price was CA $911, price is now CA $911 per person
CA $911
per person
Jul 30 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
7.8/10 Good! (1,010 reviews)
The room was very clean and quiet. The interior was modern and very well laid out. The breakfast was very good.

Reviewed on Jun 8, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was CA $2,333, price is now CA $2,139 per person
CA $2,139
per person
Jul 29 - Aug 1
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to New Haven (HVN)
No reviews

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Windsor Hotel Deals

Marriott Hartford/Windsor Airport

Marriott Hartford/Windsor Airport

3.5 out of 5
28 Day Hill Rd Windsor CT
Fully refundableReserve now, pay when you stay
The price is CA $253 per night from Jul 2 to Jul 3
CA $253
CA $291 total
Jul 2 - Jul 3
includes taxes & fees
8.4/10 Very good! (1,003 reviews)
"The front desk does not communicate with the shuttle. The chef did not follow communication from the wait staff/bartender for lunch order. Work on this!"

Reviewed on Jun 22, 2026

Marriott Hartford/Windsor Airport
Courtyard By Marriott Hartford/Windsor Airport

Courtyard By Marriott Hartford/Windsor Airport

3 out of 5
1 Day Hill Rd Windsor CT
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from Jul 5 to Jul 6
CA $167
CA $192 total
Jul 5 - Jul 6
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"Meh."

Reviewed on Jun 18, 2026

Courtyard By Marriott Hartford/Windsor Airport
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
555 Corporate Dr Windsor CT
Fully refundableReserve now, pay when you stay
The price is CA $179 per night from Jul 5 to Jul 6
CA $179
CA $206 total
Jul 5 - Jul 6
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
"Breakfast included, it was good."

Reviewed on Jun 23, 2026

Hilton Garden Inn Hartford North/Bradley Int'l Airport
See all 749 properties in Windsor
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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.

Windsor Historical Society

What to do in Windsor

Connecticut Coloured Regiment Parade Route: An Audio Tour

Connecticut Coloured Regiment Parade Route: An Audio Tour

CA $14
per adult
Connecticut Coloured Regiment Parade Route: An Audio Tour
See all activities in Windsor

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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.