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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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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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.
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
per person
Aug 22 - Aug 24
found 16 hours ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
9.2/10 Wonderful! (824 reviews)
The staff is very hospitable. She let me check in early and helped us with luggages as the elevator was out of order for a while. I really like the library set up so I was able to focus on working for a long while as my husband needs to use the desk in the room. The location is the best. I wish they had free bottled water in the room. The cafe in the lobby is very nice.

Reviewed on Jul. 6, 2025

Westbrook Inn B&B

Westbrook Inn B&B

3 out of 5
Westbrook Center
per person
Aug 24 - Aug 28
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
10/10 Exceptional! (151 reviews)
It is beautiful and comfortable. The breakfast was great. And the bed was extremely comfortable.

Reviewed on Mar. 20, 2025

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
Old Saybrook Center
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
9.4/10 Exceptional! (1,003 reviews)
Loved the service and the relaxing and beautiful resort with history!

Reviewed on Jul. 2, 2025

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
per person
Aug 22 - Aug 24
found 16 hours ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
8.4/10 Very Good! (1,003 reviews)
Area around had lots of homeless people in the park.

Reviewed on Jul. 6, 2025

The Captain Stannard

The Captain Stannard

3 out of 5
Westbrook Center
per person
Aug 24 - Aug 28
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
9.6/10 Exceptional! (227 reviews)
Very nice place and the owners are super people and treat their customers very well! I loved it here and would definitely stay here again!

Reviewed on Jun. 2, 2025

Ready to book your vacation to Windsor?

 

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Windsor Hotel Deals

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 $172 per night from Jul 13 to Jul 14
CA $172
CA $198 total
Jul 13 - Jul 14
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"The view was stunning and the hotel was very clean. Would definitely stay again"

Reviewed on Jun. 18, 2025

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 $257 per night from Jul 11 to Jul 12
CA $257
CA $296 total
Jul 11 - Jul 12
includes taxes & fees
8.4/10 Very Good! (1,005 reviews)
"Staff friendly, hotel was clean, spacious room. Breakfast not included."

Reviewed on Jun. 22, 2025

Marriott Hartford/Windsor Airport
Residence Inn by Marriott Hartford/Windsor
Residence Inn by Marriott Hartford/Windsor
3 out of 5
100 Dunfey Ln, Windsor, CT
Fully refundableReserve now, pay when you stay
The price is CA $205 per night from Jul 13 to Jul 14
CA $205
CA $236 total
Jul 13 - Jul 14
includes taxes & fees
8.2/10 Very Good! (610 reviews)
"Great to have an indoor pool where the kids could play together. The breakfast had plenty of options. Overall this was a good place to stay for a baseball tournament."

Reviewed on Jun. 30, 2025

Residence Inn by Marriott Hartford/Windsor
See all 670 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

Frequently asked questions

How much does a Windsor vacation package cost?
Offering great value package deals from CA $637 on Expedia, you'll be surprised at how little a vacation to Windsor costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Windsor?
If you're looking to score a cheap Windsor vacation package, consider planning a trip in December, January and February. You'll generally find lower rates on flights and hotels during these months --- perfect for travellers wishing to save money.
How many days is enough for Windsor?
With about 2 days, you'll have enough time to enjoy popular neighbourhoods such as Downtown Hartford and North Meadows during your Windsor vacation. Make sure to also add Shoppes at Buckland Hills and Promenade Shops at Evergreen Walk to your must-see list. Looking for more adventures? Consider venturing outside of Windsor on day trips and tours.
Is it worth booking a vacation package to Windsor?
Whether you're looking to explore attractions such as Oliver Ellsworth Homestead and Windsor Meadows State Park on your Windsor vacation, or coming for its excellent history, festivals and culture, there's something for everyone here. With so much to see and do, you'll soon discover why so many people think Windsor is a good vacation destination.
How to find the best Windsor package deals?
Finding a cheap Windsor package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, add a couple of filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most economical Windsor package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Windsor vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Windsor vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Windsor?
If you're considering a spontaneous Windsor adventure, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can score incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Windsor?

  1. Choose when to travel: Check your diary and get your bags packed. Your favourite time of year and the type of activities on offer will also help you decide when to escape to Windsor.
  2. Set a budget: Factor in expenses like flights, meals and transportation when working out how much to put aside for your trip to Windsor. Then, choose a hotel that fits your budget, whether that's a wallet-friendly option or a more upscale getaway.
  3. Decide how long to go away for: Now that you know more about Windsor, you can work out the perfect length of your break. Put together a rough itinerary and give yourself enough time to get through everything on your must-do list.
  4. Bundle your airfare and accommodations: After you've nailed down your trip dates and duration, lock in the ideal Windsor vacation package for you.

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