Windsor Vacations
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Find the Best Windsor Vacation Packages
Windsor Hotel Deals
Marriott Hartford/Windsor Airport
28 Day Hill Rd Windsor CT
Fully refundableReserve now, pay when you stay
₩240,445
₩276,512 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
₩213,995
₩246,094 total
Sep 6 - Sep 7
includes taxes & fees
Hilton Garden Inn Hartford North/Bradley Int'l Airport
555 Corporate Dr Windsor CT
Fully refundableReserve now, pay when you stay
₩172,012
₩197,814 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 473 acres of diverse habitats through 12 miles of scenic trails at this natural retreat. The nature center's educational exhibits and heritage breed farm create an immersive outdoor experience for all ages.
Loomis Chaffee School
This prestigious New England boarding school blends historic architecture with state-of-the-art facilities. Schedule a guided campus tour to experience Loomis Chaffee's innovative learning spaces and picturesque grounds.
Windsor Arts Center
7.6/10 (18 reviews)
This historic freight house turned art center showcases contemporary New England art in a charming railway setting. Enjoy rotating exhibitions while soaking in the creative atmosphere of Windsor's cultural hub.
Oliver Ellsworth Homestead
8.2/10 (15 reviews)
Step back in time at Elmwood, home of Oliver Ellsworth who helped draft the U.S. Constitution. Explore period furnishings and family artifacts in this beautifully preserved 18th-century residence.
Vintage Radio and Communications Museum of Connecticut
7.6/10 (13 reviews)
This time-traveling museum showcases communication technology from the 1800s to modern computers. Tap out Morse code messages and tune vintage radios while knowledgeable volunteers bring history to life.
Windsor Historical Society
8.0/10 (12 reviews)
Step into Connecticut's oldest English settlement at the Windsor Historical Society's museum complex. Explore two historic homes dating to the 1700s and try on colonial costumes in the hands-on learning center.
Windsor Meadows State Park
7.6/10 (10 reviews)
This riverside haven offers peaceful trails winding through floodplain forests with Connecticut River views. Explore the meadows or launch your boat for a day of fishing and serene water adventures.
Frequently asked questions
How much does a Windsor vacation package cost?
You'll find cheap prices on Expedia for your Windsor break. However, a range of factors like the season, choice of hotel and length of stay will influence how much your vacation to Windsor costs.
What are the cheapest months to go to Windsor?
You can typically find lower rates and greater availability in December, January and February. Explore our cheap Windsor vacation packages and you could score some great off-season discounts.
How many days is enough for Windsor?
With about 2 days, you'll have enough time to visit popular neighborhoods like Downtown Hartford and North Meadows during your Windsor vacation. Be sure to also add Oliver Ellsworth Homestead and SS&C SummerWind Performing Arts Center to your list of must-sees. In the mood for more adventures? Consider exploring outside of Windsor on tours and day trips.
Is it worth booking a vacation package to Windsor?
Whether you want to check out top sights such as Oliver Ellsworth Homestead and Windsor Meadows State Park on your Windsor vacation, or coming for its great history, festivals and culture, there's something for everyone here. With so many things to see and do, you'll quickly learn why so many visitors think Windsor is a good vacation destination.
How to find the best Windsor package deals?
Bagging a cheap Windsor package deal is a cinch with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can customize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Windsor package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Windsor vacation as a package?
You can enjoy significant savings on your next Windsor getaway by booking a personalized vacation package. Click on the "Package" heading, then select your destination and travel dates to view the best hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Windsor?
If you're planning a spur-of-the-moment Windsor vacation, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to Windsor?
- Pick your travel dates: What you want to do in Windsor and your preferred season will help you decide when to go.
- Budget wisely: Besides the price of your stay, you should consider other expenses too. These include food, flights and transportation. Also, put aside a little extra for unexpected expenses that could crop up during your trip to Windsor.
- Decide your trip length: Consider how much time you'd like to spend exploring Windsor. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a customized Windsor vacation package.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
