Windsor Vacations from $326

Book a Hotel + Flight or Car together to unlock savings

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.
Holiday Inn Express Southington, an IHG Hotel

Holiday Inn Express Southington, an IHG Hotel

2.5 out of 5
per person
Jul 18 - Jul 21
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
8.4/10 Very Good! (1,001 reviews)
The property was well kept and clean

Reviewed on May 26, 2024

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
per person
Aug 16 - Aug 18
found 2 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to New Haven (HVN)
8.8/10 Excellent! (1,003 reviews)
This property is great if you need a quiet, near the airport hotel.. Thanks

Reviewed on Jun 3, 2024

Simsbury Inn

Simsbury Inn

3.5 out of 5
Simsbury Center
per person
Aug 16 - Aug 18
found 2 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to New Haven (HVN)
9.2/10 Wonderful! (168 reviews)
Some strange lint-like substance came out of the bath faucet

Reviewed on Jun 5, 2024

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
per person
Jul 18 - Jul 21
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
8.8/10 Excellent! (351 reviews)
Clean, elegant design, lots of natural light, window seats in the bedroom. Very gracious and helpful front desk staff

Reviewed on May 30, 2024

Hampton Inn Hartford/Airport

Hampton Inn Hartford/Airport

2.5 out of 5
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
San Jose (SJC) to New Haven (HVN)
9/10 Wonderful! (912 reviews)
Staff was excellent

Reviewed on Jun 3, 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 $126 per night from Jul 7 to Jul 8
$126
$145 total
includes taxes & fees
Jul 7 - Jul 8
9/10 Wonderful! (1,007 reviews)
Little business, all pleasure
"I had an amazing stay. I love the setup, look and feel of this hotel. The staff was welcoming and inviting. I will definitely stay here again."

Reviewed on Jun 1, 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 23 to Jun 24
$127
$146 total
includes taxes & fees
Jun 23 - Jun 24
8.6/10 Excellent! (1,003 reviews)
"This property is great if you need a quiet, near the airport hotel.. Thanks"

Reviewed on Jun 3, 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 Jul 1 to Jul 2
$179
$206 total
includes taxes & fees
Jul 1 - Jul 2
8.4/10 Very Good! (1,005 reviews)
"Super clean, beautifully decorated...a real gem."

Reviewed on Jun 3, 2024

Marriott Hartford/Windsor Airport
See all 605 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.

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 $326, 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 Arts Center

Windsor Arts Center

5/5(2 reviews)

Rich with history, Windsor Arts Center is a cultural attraction worth visiting in Windsor. Experience the area's acclaimed theater scene or attend a sporting event.

Windsor Arts Center
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.