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.
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
per person
Oct 24 - Oct 27
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
8.8/10 Excellent! (1,009 reviews)
NICE STAFF, GREEN HOTEL, GREAT BAR AND RESTAURANT.

Reviewed on Aug. 1, 2025

Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

2.5 out of 5
per person
Oct 24 - Oct 27
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
8.8/10 Excellent! (1,735 reviews)
Quick , easy fairly clean ( room smelled a little musty ) but wverything else was clean and comfortable

Reviewed on Aug. 5, 2025

Residence Inn by Marriott New Haven Hamden

Residence Inn by Marriott New Haven Hamden

3 out of 5
per person
Sep 8 - Sep 14
found 7 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to New Haven (HVN)
9.4/10 Exceptional! (369 reviews)
It’s always pleasant when I stay here.

Reviewed on Jul. 8, 2025

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
per person
Sep 8 - Sep 14
found 7 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to New Haven (HVN)
9.2/10 Wonderful! (851 reviews)
Great location and was able to park right out front on a Sunday.

Reviewed on Jul. 25, 2025

La Quinta Inn & Suites by Wyndham New Haven

La Quinta Inn & Suites by Wyndham New Haven

3 out of 5
Long Wharf
per person
Sep 8 - Sep 14
found 7 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to New Haven (HVN)
6/10 (1,057 reviews)
The room was drab but comfortable. The hotel is showing its age and is being refreshed, so the lobby was torn up under construction. The breakfast was the typical cheap minimum.

Reviewed on Aug. 4, 2025

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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 $174 per night from Sep 1 to Sep 2
CA $174
CA $201 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
ready to stay again
"Great stay. Stayed at the nearby Hampton Inn before and this was much, much better."

Reviewed on Aug. 4, 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 $219 per night from Aug 15 to Aug 16
CA $219
CA $252 total
Aug 15 - Aug 16
includes taxes & fees
8.4/10 Very Good! (1,003 reviews)
"The airport shuttle was very helpful for our family whose flight had been cancelled."

Reviewed on Aug. 5, 2025

Marriott Hartford/Windsor Airport
HYATT house Hartford North/Windsor

HYATT house Hartford North/Windsor

3 out of 5
200 Corporate Dr, Windsor, CT
Fully refundableReserve now, pay when you stay
The price is CA $198 per night from Aug 17 to Aug 18
CA $198
CA $228 total
Aug 17 - Aug 18
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"."

Reviewed on Jul. 29, 2025

HYATT house Hartford North/Windsor
See all 668 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 $598 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.