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.
Hyatus Luxury Residences City Crossing
The Hill
CA $1,186
per person
Oct 16 - Oct 18
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
9.4/10 Exceptional! (33 reviews)
Everything about the property & staff was AMAZING! Zero complaints, would 100% stay there again if in the area. Thank you!
Reviewed on Jul 24, 2026
Ready to book your vacation to Windsor?
Windsor Hotel Deals
Marriott Hartford/Windsor Airport
28 Day Hill Rd Windsor CT
Fully refundableReserve now, pay when you stay
CA $237
CA $272 total
Aug 28 - Aug 29
includes taxes & fees
8.4/10 Very good! (1,003 reviews)
"Very clean and helpful staff."
Reviewed on Jul 31, 2026
Courtyard By Marriott Hartford/Windsor Airport
1 Day Hill Rd Windsor CT
Fully refundableReserve now, pay when you stay
CA $213
CA $245 total
Sep 7 - Sep 8
includes taxes & fees
Hilton Garden Inn Hartford North/Bradley Int'l Airport
555 Corporate Dr Windsor CT
Fully refundableReserve now, pay when you stay
CA $171
CA $197 total
Aug 16 - Aug 17
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
"We had to wait 4 hours for our room to be ready. We arrived at 4 pm."
Reviewed on Aug 6, 2026
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.
Stay near popular Windsor attractions
Northwest Park
7.8/10 (24 reviews)
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.
Loomis Chaffee School
Enjoy the collegiate vibe at Loomis Chaffee School as part of your travels around Windsor. While in this family-friendly area, you can savor the top-notch restaurants.
Windsor Arts Center
7.6/10 (18 reviews)
Enjoy an outing to Windsor Arts Center during your stay in Windsor. Experience the area's acclaimed theater scene or attend a sporting event.
Oliver Ellsworth Homestead
8.2/10 (15 reviews)
Find out about the history of Windsor with a stop at Oliver Ellsworth Homestead. Experience the area's great live music and acclaimed theater scene.
Vintage Radio and Communications Museum of Connecticut
7.6/10 (13 reviews)
You can study the exhibits at Vintage Radio and Communications Museum of Connecticut, a museum with a storied past, during your travels to Windsor. Experience the area's great live music or attend a sporting event.
Windsor Historical Society
8.0/10 (12 reviews)
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 Meadows State Park
7.6/10 (10 reviews)
You can take time to visit Windsor Meadows State Park during your travels to Windsor. While in this family-friendly area, you can savor the top-notch restaurants.
What to do in Windsor
Connecticut Coloured Regiment Parade Route: An Audio Tour
CA $14
per adult
Frequently asked questions
How much does a Windsor vacation package cost?
Offering great value package deals from CA $540 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?
- 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.
- 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.
- 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.
- 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.
