Windsor Vacations from $418

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Your Windsor Vacation

Choose a Windsor vacation package and you can focus on what matters — having some fun. There's no more stressful planning, just lots more time to experience the best of this awesome city, such as its cosmopolitan vibe and rich history. If taking in sights is part of the plan during your trip to Windsor, stop by major attractions like Xfinity Theatre, XL Center and University of Hartford. Don't put off exploring this destination any longer. The perfect Windsor vacation is a couple of clicks away with Expedia.

The Latest Windsor Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham West Haven

Super 8 by Wyndham West Haven

2 out of 5
per person
Jul 10 - Jul 16
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
4.8/10 (912 reviews)
Staff are very friendly and helpful

Reviewed on Sep 26, 2023

La Quinta Inn & Suites by Wyndham New Haven

La Quinta Inn & Suites by Wyndham New Haven

2.5 out of 5
Long Wharf
per person
Jul 10 - Jul 16
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
5.4/10 (1,004 reviews)
Stayed overnight while traveling through the area. Clean but no frills.

Reviewed on May 19, 2024

New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
per person
Jul 10 - Jul 16
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
8.8/10 Excellent! (1,233 reviews)
Stayed only one night, location was quite close to Yale, within walking distance. Staff was friendly. Room was big but lots of unused space tbh.

Reviewed on May 21, 2024

Holiday Inn Express Southington, an IHG Hotel

Holiday Inn Express Southington, an IHG Hotel

2.5 out of 5
per person
Jun 27 - Jun 30
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
8.4/10 Very Good! (1,009 reviews)
Everything was clean and staff was friendly. The bedding and pillows were very comfortable and fluffy. Very nice stay.

Reviewed on May 21, 2024

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
per person
Jul 10 - Jul 16
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
8.2/10 Very Good! (999 reviews)
Very good location to walk to most areas. Rooms were clean and beds were comfortable.

Reviewed on May 17, 2024

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

Windsor Hotel Deals

HYATT house Hartford North/Windsor
HYATT house Hartford North/Windsor
3 out of 5
200 Corporate Dr, Windsor, CT
Fully refundable
The price is $118 per night from May 29 to May 30
$118
$136 total
includes taxes & fees
May 29 - May 30
9/10 Wonderful! (1,001 reviews)
"Very friendly and helpful staff."

Reviewed on May 20, 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 $127 per night from Jun 2 to Jun 3
$127
$146 total
includes taxes & fees
Jun 2 - Jun 3
8.6/10 Excellent! (1,001 reviews)
Roe's Review
"Overall a great team, great customer service except when we first arrived and checked in."

Reviewed on May 13, 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 $179 per night from May 23 to May 24
$179
$206 total
includes taxes & fees
May 23 - May 24
8.4/10 Very Good! (1,001 reviews)
"The rooms were very clean"

Reviewed on May 12, 2024

Marriott Hartford/Windsor Airport
See all 593 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Windsor vacation package cost?
Starting from only $418, 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 vacation 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 vacation.
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 Center. 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 vacation?
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 vacation plans, there’s bound to be a package to suit your budget.
Can I choose my airline with a Windsor Expedia vacation 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 vacation 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.

Discover the most popular places to visit in Windsor

Image for Northwest Park

Northwest Park

4.5/5(4 reviews)

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
Image for Windsor Historical Society

Windsor Historical Society

5/5(4 reviews)

You can spend an afternoon browsing the exhibits at Windsor Historical Society during your trip to Windsor. Experience the great live music or attend a sporting event in this family-friendly area.

Windsor Historical Society
Image for SS&C SummerWind Performing Arts Center

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 acclaimed theater scene or attend a sporting event.

SS&C SummerWind Performing Arts Center

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.