Windsor Vacations

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    Save up to AEDĀ 5,000 when you book a flight and hotel together*

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Find the Best Windsor Vacation Packages

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
The price is AEDĀ 547 per night from Dec 11 to Dec 12
AEDĀ 547
AEDĀ 629 total
11 Dec - 12 Dec
includes taxes & fees
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 AEDĀ 460 per night from Nov 22 to Nov 23
AEDĀ 460
AEDĀ 528 total
22 Nov - 23 Nov
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"Nice hotel with clean rooms and good amenities. We went there for a soccer tournament so the location was perfect. Would definitely recommend and stay there again next time need an overnight in that area."

Reviewed on 11 November 2026

HYATT house Hartford North/Windsor
Courtyard By Marriott Hartford/Windsor Airport

Courtyard By Marriott Hartford/Windsor Airport

3 out of 5
1 Day Hill Rd Windsor CT
Fully refundableReserve now, pay when you stay
The price is AEDĀ 526 per night from Dec 4 to Dec 5
AEDĀ 526
AEDĀ 604 total
4 Dec - 5 Dec
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
"dining room and bar hours to short"

Reviewed on 11 November 2026

Courtyard By Marriott Hartford/Windsor Airport
See all 797 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.

Stay near popular Windsor attractions

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.
See properties

Frequently asked questions

How much does a Windsor vacation package cost?
Offering great value package deals 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 ā€” perfect for travelers wishing to save money.
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 favorite 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 favorite 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.