Windsor Vacations from $867

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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.
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $1,170, price is now $867 per person
$867
per person
Oct 9 - Oct 14
found 17 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.2/10 Wonderful! (861 reviews)
Great hotel, comfortable beds, clean property. Ideal location, close to Yale

Reviewed on Aug 24, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Save 100% on your flight
Price was $2,637, price is now $1,607 per person
$1,607
per person
Oct 9 - Oct 14
found 17 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
No reviews
Madison Beach Hotel

Madison Beach Hotel

4 out of 5
Madison Center
Save 100% on your flight
Price was $1,352, price is now $962 per person
$962
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
9.4/10 Exceptional! (312 reviews)
The hotel is beautiful and the grounds are wonderful. The staff was top notch. We will definitely stay again.

Reviewed on Aug 18, 2025

Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
The Hill
Save 100% on your flight
Price was $1,405, price is now $1,035 per person
$1,035
per person
Oct 9 - Oct 14
found 17 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.4/10 Exceptional! (19 reviews)
Excellent location downtown and close to yale. A lot of complimentary amenities and activities. Very nice size rooms. A nice residential feel for a weeks stay.

Reviewed on Jun 27, 2025

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $1,385, price is now $1,047 per person
$1,047
per person
Oct 9 - Oct 14
found 17 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.4/10 Very Good! (1,008 reviews)
I wish I would’ve known that the hotel sits along and extremely noisy strip of bars. Honking cars and all kinds of shouting and crowd noise into the early morning made trying to sleep here unpleasant. The staff was friendly though it seemed like the reception was understaffed. It took a while for us to be buzzed in from the parking garage which was unpleasant late at night.

Reviewed on Aug 23, 2025

Don't see what you're looking for?
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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

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
$159 nightly
The price is $183 total per night from Aug 29 to Aug 30
$183 total
Aug 29 - Aug 30
Total with taxes and fees
8.4/10 Very Good! (1,005 reviews)
"Bed was comfortable and room was spacious and nice"

Reviewed on Aug 18, 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
$144 nightly
The price is $166 total per night from Aug 31 to Sep 1
$166 total
Aug 31 - Sep 1
Total with taxes and fees
9/10 Wonderful! (1,003 reviews)
"Back patio needs some repairs"

Reviewed on Aug 14, 2025

HYATT house Hartford North/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
$127 nightly
The price is $146 total per night from Sep 1 to Sep 2
$146 total
Sep 1 - Sep 2
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
Would definitely stay here again
"Clean, comfortable, close to BDL, restaurant/bar in building, attractive outdoor area. Just what I needed on this trip."

Reviewed on Aug 21, 2025

Hilton Garden Inn Hartford North/Bradley Int'l Airport
See all 672 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.

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Frequently asked questions

How much does a Windsor vacation package cost?
You'll find cheap prices from $867 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.