Windsor Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Windsor

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 S$157 per night from 2 Dec to 3 Dec
S$157
includes taxes & fees
2 Dec - 3 Dec
9/10 Wonderful! (1,003 reviews)
"Very happy with our choice of hotel for five nights. The staff was very friendly whenever encountered. Breakfast was good, however, I usually have oatmeal. The other options looked tasty. The facitily was spotless. Would definitely stay here again."

Reviewed on 22 Nov,2024

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
The price is S$183 per night from 22 Dec to 23 Dec
S$183
includes taxes & fees
22 Dec - 23 Dec
8.6/10 Excellent! (1,000 reviews)
"Nice place. Gym was lacking. Staff is terrific. Nice balcony but all around the place is parking lot."

Reviewed on 15 Nov,2024

Hilton Garden Inn Hartford North/Bradley Int'l Airport
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 S$231 per night from 6 Dec to 7 Dec
S$231
includes taxes & fees
6 Dec - 7 Dec
8.4/10 Very Good! (1,000 reviews)
"The room was nice, the bed was very comfortable! The carpets throughout the hotel were refreshingly, very clean. The breakfast buffet was very good, and the staff was great. Our waitress, Nancy, was absolutely amazing! She took care of us and all of her guests, as if we were family! She loves her ..."

Reviewed on 18 Nov,2024

Marriott Hartford/Windsor Airport
See all 674 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.

Frequently asked questions

How much does a Windsor holiday package cost?
Starting from only , a package is your passport to cheaper travel. Build your own Windsor trip by choosing from our great range of hotels, flights and rental cars.
How do I get a cheap travel package to Windsor?
Crafting your own Windsor holiday package with Expedia is a smart way to save. We have over 550 airlines and 1,000,000 hotel options throughout the world. With such a fantastic range to choose from, you’ll have no difficulty pulling together your ideal holiday.
Where should I stay in Windsor?
A trip to Windsor isn’t complete without paying a visit to Nomads Adventure Quest, Northwest Park and Windsor Arts Centre. Spend your nights close to these popular attractions and make sightseeing easy.
What are the top hotels in Windsor?
HYATT house Hartford North/Windsor and Residence Inn by Marriott Hartford/Windsor are a couple of the most well-known properties in Windsor. Why not check out the facilities and rates at each and then decide?
How far in advance should I book my Windsor holiday?
Search Expedia to compare airfares as soon as you know your travel dates. You can normally purchase a ticket up to 12 months before departure. If you don’t see your preferred carrier, or you have to book last minute, fear not. Cheap tickets to Windsor occasionally appear within weeks of departure.
What does an Expedia Windsor travel package include?
With Expedia, you can select any combination of hotels, car rentals and flights to build your perfect Windsor package. Once you’ve made your booking, you can add on all the fun stuff like sightseeing tours and activities. Remember — the more you bundle, the more cash you’ll save!
What should I know before booking a Windsor travel package?
A package can be more affordable than individually booking everything you need for your adventure. For example, combine your flights, hotels and rental cars and land a great deal. No matter your holiday plans, there’s bound to be a package to suit your budget.
Can I choose my airline with a Windsor Expedia holiday package?
Expedia offers access to more than 550 partner airlines worldwide, so you certainly can. Simply choose your preferred air carrier and create your ideal Windsor trip.
If I'm not able to travel, can I cancel my Windsor holiday package?
You can cancel your Windsor booking if your travel plans have been upended. Whether you’ll be charged a fee or not depends on your hotel, airline or car rental company. It may be possible to cancel or change free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.