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.
Holiday Inn Express Southington, an IHG Hotel

Holiday Inn Express Southington, an IHG Hotel

2.5 out of 5
per person
Jun. 12 - Jun. 17
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
8.4/10 Very Good! (988 reviews)
Rooms are clean staff very kind and professional can't beat the free breakfast alot of good options

Reviewed on May 3, 2024

Village Motel By OYO Clinton

Village Motel By OYO Clinton

2.5 out of 5
per person
Jun. 12 - Jun. 17
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
10/10 Exceptional! (1 review)
For the price it’s a great deal. Very private country vibes at this motel.

Reviewed on Apr. 30, 2024

Super 8 by Wyndham Old Saybrook

Super 8 by Wyndham Old Saybrook

2 out of 5
per person
Jun. 20 - Jun. 24
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
7/10 Good! (800 reviews)
It’s clean and convenient off I95

Reviewed on Apr. 12, 2024

New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
per person
Jun. 12 - Jun. 17
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
8.8/10 Excellent! (1,214 reviews)
Nice and clean hotel with friendly and helpful staff.

Reviewed on Apr. 30, 2024

Residence Inn by Marriott Hartford/Windsor

Residence Inn by Marriott Hartford/Windsor

3 out of 5
per person
Jun. 12 - Jun. 17
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
8.4/10 Very Good! (475 reviews)
Overall the two room suite was perfect for our needs. However, the room need a bit of updating and a deep cleaning.

Reviewed on Apr. 22, 2024

Windsor Hotel Deals

HYATT house Hartford North/Windsor
HYATT house Hartford North/Windsor
3 out of 5
200 Corporate Dr, Windsor, CT
Fully refundable
The price is CA $152 per night from May 26 to May 27
CA $152
CA $174 total
includes taxes & fees
May 26 - May 27
9/10 Wonderful! (1,003 reviews)
"I really enjoyed my stay here. Check-in was easy. Room was quiet and incredibly spacious. Bed was comfortable. Air conditioner worked really well. Overall a great experience. Only negative things I can say is that water from the shower got all over bathroom floor. However, I was in a handicap accessible ..."

Reviewed on Apr. 27, 2024

HYATT house Hartford North/Windsor
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
The price is CA $168 per night from May 19 to May 20
CA $168
CA $193 total
includes taxes & fees
May 19 - May 20
8.6/10 Excellent! (1,001 reviews)
"Your employees were amazing"

Reviewed on Apr. 22, 2024

Hilton Garden Inn Hartford North/Bradley Int'l Airport
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 $231 per night from May 10 to May 11
CA $231
CA $266 total
includes taxes & fees
May 10 - May 11
8.4/10 Very Good! (1,001 reviews)
"Excellent!"

Reviewed on Apr. 30, 2024

Marriott Hartford/Windsor Airport
See all 598 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Windsor vacation package cost?
Starting from only CA $581, a package is your passport to cheaper travel. Build your own Windsor trip by choosing from our great range of hotels, flights and rental cars.
How do I get a cheap travel package to Windsor?
Crafting your own Windsor vacation package with Expedia is a smart way to save. We have over 550 airlines and 1,000,000 hotel options throughout the world. With such a fantastic range to choose from, you’ll have no difficulty pulling together your ideal vacation.
Where should I stay in Windsor?
A trip to Windsor isn’t complete without paying a visit to Nomads Adventure Quest, Northwest Park and Windsor Arts Center. Spend your nights close to these popular attractions and make sightseeing easy.
What are the top hotels in Windsor?
HYATT house Hartford North/Windsor and Residence Inn by Marriott Hartford/Windsor are a couple of the most well-known properties in Windsor. Why not check out the facilities and rates at each and then decide?
How far in advance should I book my Windsor vacation?
Search Expedia to compare airfares as soon as you know your travel dates. You can normally purchase a ticket up to 12 months before departure. If you don’t see your preferred carrier, or you have to book last minute, fear not. Cheap tickets to Windsor occasionally appear within weeks of departure.
What does an Expedia Windsor travel package include?
With Expedia, you can select any combination of hotels, car rentals and flights to build your perfect Windsor package. Once you’ve made your booking, you can add on all the fun stuff like sightseeing tours and activities. Remember — the more you bundle, the more cash you’ll save!
What should I know before booking a Windsor travel package?
A package can be more affordable than individually booking everything you need for your adventure. For example, combine your flights, hotels and rental cars and land a great deal. No matter your vacation plans, there’s bound to be a package to suit your budget.
Can I choose my airline with a Windsor Expedia vacation package?
Expedia offers access to more than 550 partner airlines worldwide, so you certainly can. Simply choose your preferred air carrier and create your ideal Windsor trip.
If I'm not able to travel, can I cancel my Windsor vacation package?
You can cancel your Windsor booking if your travel plans have been upended. Whether you’ll be charged a fee or not depends on your hotel, airline or car rental company. It may be possible to cancel or change free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.

Discover the most popular places to visit in Windsor

Image for Northwest Park

Northwest Park

Explore the great outdoors at Northwest Park, a lovely green space in Windsor. Experience the area's great live music or attend a sporting event.

Northwest Park
Image for Windsor Historical Society

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
Image for Windsor Arts Center

Windsor Arts Center

Rich with history, Windsor Arts Center is a cultural attraction worth visiting in Windsor. Experience the area's acclaimed theater scene or attend a sporting event.

Windsor Arts Center
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.