Windsor Vacations from $409

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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.

The Latest Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
Quality Suites Stratford

Quality Suites Stratford

2.5 out of 5
Price was $462, price is now $409 per person
$409
per person
Mar 17 - Mar 21
found 1 hour ago
Roundtrip flight included
San Francisco (SFO) to New Haven (HVN)
8/10 Very Good! (1,005 reviews)
Excellent place! Super clean, nice staff, great breakfast, comfortable!

Reviewed on Nov 26, 2025

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Discover the most popular places to visit in Windsor

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

SS&C SummerWind Performing Arts Center

Enjoy a show at SS&C SummerWind Performing Arts Center, a storied theater in Windsor. Experience the area's great live music or attend a sporting event.

SS&C SummerWind Performing Arts Center

Windsor Hotel Deals

Hampton Inn Hartford/Airport

Hampton Inn Hartford/Airport

2.5 out of 5
2168 Poquonock Ave Windsor CT
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $131 total per night from Jan 25 to Jan 26
$131 total
Jan 25 - Jan 26
Total with taxes and fees
9/10 Wonderful! (1,005 reviews)
Second time here, breakfast was always fresh, pool was clean and staff was friendly. My son and I loved the hot chocolate bar with the coffee and tea all day. It was such a nice touch visiting around the holidays

Reviewed on Dec 31, 2025

Hampton Inn Hartford/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
$113 nightly
The price is $130 total per night from Feb 3 to Feb 4
$130 total
Feb 3 - Feb 4
Total with taxes and fees
8.2/10 Very Good! (687 reviews)
The room was very spacious, with a separate downstairs master suite and upstairs loft bedroom/bath. The staff was very accommodating to any need we had and checked on us throughout our stay. Our only "complaint" was that the breakfast was either soggy or hars but they did have a wide selection. We ...

Reviewed on Dec 25, 2025

Residence Inn by Marriott Hartford/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
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $131 total per night from Jan 19 to Jan 20
$131 total
Jan 19 - Jan 20
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
It was fine ty

Reviewed on Dec 22, 2025

Hilton Garden Inn Hartford North/Bradley Int'l Airport
See all 742 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.

Find the Best Windsor Vacation Packages

Windsor Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Population
28,800
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Xfinity Theatre, Connecticut Science Center and Talcott Mountain State Park

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Frequently asked questions

How much does a Windsor vacation package cost?
You'll find cheap prices from $409 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?
If you're looking to score a cheap Windsor vacation package, consider visiting in December, January and February. You're likely to find better prices on hotels and airfares during these quieter months — ideal for a budget-friendly break.
How many days is enough for Windsor?
We recommend planning a Windsor vacation for around 2 days. This will allow you time to visit popular sights such as Northwest Park and Oliver Ellsworth Homestead, and check out neighborhoods like Downtown Hartford and North Meadows. You might even be able to fit in a day trip or two beyond Windsor.
Is it worth booking a vacation package to Windsor?
Whether you're looking to explore attractions such as Windsor Arts Center and Windsor Historical Society on your Windsor vacation, or coming for its excellent history, festivals and culture, there's something for everyone here. With so many things to do, you'll soon learn why so many travelers 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?

  1. Choose the best time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to visit Windsor.
  2. Plan your budget wisely: As well as the price of your accommodations, you should consider other expenses too. These include flights, transportation and food. Also, put aside some extra funds for unexpected expenses that may crop up during your trip to Windsor.
  3. Organize your Windsor escape with Expedia's trip planning tool: Look for and book accommodations and activities all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Windsor together.
  4. Work out your trip length: Consider how long you'd like to spend discovering Windsor. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
  5. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a personalized Windsor vacation package.
  6. Add on experiences and excursions: Read our travel guide to find some fun things to do in Windsor. Book tickets or make reservations in advance to save time and avoid the stress of searching for activities when you arrive.

Does Expedia offer Book Now, Pay Later Windsor vacation packages?
Your Windsor getaway is meant to be an escape from your busy life, not a reason for money-related stress. So to give you more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

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.