Deals on vacations and trips to Windsor

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Windsor flight + hotel vacation packages

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Fairfield by Marriott Inn & Suites Madison South

Fairfield by Marriott Inn & Suites Madison South

3 out of 5
Price was $775, price is now $670 per person
$670
per person
Jul 29 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
St. Louis (STL) to Madison (MSN)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
Downtown Madison
Price was $1,301, price is now $1,041 per person
$1,041
per person
Jul 29 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
St. Louis (STL) to Madison (MSN)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.
Graduate by Hilton Madison

Graduate by Hilton Madison

4 out of 5
Downtown Madison
Price was $1,424, price is now $1,191 per person
$1,191
per person
Jul 29 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
St. Louis (STL) to Madison (MSN)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas and valet parking. There's a rooftop terrace on site, and a 24-hour front desk and a coffee shop are also provided.
Home2 Suites by Hilton Madison Central Alliant Energy Center

Home2 Suites by Hilton Madison Central Alliant Energy Center

3 out of 5
Price was $968, price is now $832 per person
$832
per person
Jul 29 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
St. Louis (STL) to Madison (MSN)
This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Dellshire Resort

Dellshire Resort

3.5 out of 5
Price was $874, price is now $758 per person
$758
per person
Jul 20 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
St. Louis (STL) to Madison (MSN)
This smoke-free hotel features 3 restaurants, 3 indoor pools, and a hot tub. There's fun for all ages with a children's pool and a waterslide, and families will appreciate the onsite laundry facilities. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi.

Top Windsor hotels deals

Days Inn by Wyndham Madison NE/Windsor

Days Inn by Wyndham Madison NE/Windsor

2 out of 5
6311 Rostad Dr Windsor WI
Free Cancellation
Reserve now, pay when you stay
$68 nightly
The price is $72 total per night
$72 total
Jun 14 - Jun 15
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like on-the-go breakfast and free self parking.
Pool
Hot Tub
The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St Madison WI
Free Cancellation
Reserve now, pay when you stay
$139 nightly
The price is $161 total per night
$161 total
Jun 14 - Jun 15
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.
Pool
Hot Tub
Best Western Plus InnTowner Madison

Best Western Plus InnTowner Madison

3 out of 5
2424 University Avenue Madison WI
Free Cancellation
Reserve now, pay when you stay
$120 nightly
The price is $139 total per night
$139 total
Jun 28 - Jun 29
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free perks like buffet breakfast and free self parking. Enjoy the hot tub and conveniences like a 24-hour front desk and laundry facilities.
Pool
Hot Tub
DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East

4 out of 5
4402 E Washington Ave Madison WI
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $113 total per night
$113 total
Jun 14 - Jun 15
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Pet friendly
Tru by Hilton Madison West, WI

Tru by Hilton Madison West, WI

2.5 out of 5
8102 Watts Rd. Madison WI
Free Cancellation
Reserve now, pay when you stay
$80 nightly
The price is $92 total per night
$92 total
Jun 29 - Jun 30
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's a 24-hour gym on site, and a 24-hour front desk and a terrace are also provided.
Breakfast included
Pet friendly
Madison Marriott South

Madison Marriott South

3.5 out of 5
706 John Nolen Dr Madison WI
Free Cancellation
Reserve now, pay when you stay
$144 nightly
The price is $166 total per night
$166 total
Jun 29 - Jun 30
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Pool
Parking included
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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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University of Wisconsin-Madison

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Historic Arched Entry to Camp Randall Stadium

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Madison Wisconsin Isthmus and Capitol at sunrise

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Frequently asked questions

How much are vacation packages to Windsor?
Travelocity provides flight and hotel vacation packages starting from just $670. With such huge savings, you'll be exploring all of Windsor in a flash.
How long should my Windsor vacation be?
Many travelers choose to spend about 2 nights in Windsor, but it's your call. If you want to venture out and explore all the exciting things this location has waiting for you, why not hang around another night or two?
Where can I get the best vacation package deals for Windsor?
It's difficult to beat Travelocity when it comes to finding your Windsor package deal. There are at least 400 air carriers and 1,000,000 properties worldwide to select from. Reserve your trip now and get ready to cross another exciting place off your must-visit list.
Why should I purchase my Windsor vacation package via Travelocity?
By booking your hotel, flights, activities and car rental all in the one place, you'll save both time and money. All our bookings come with round-the-clock customer support, and you'll know that you'll always score the lowest price possible with our Price Match Guarantee. So, what are you waiting for? Book the vacation of your dreams today and get packing!
Can I save on my Windsor car rental if I combine it with a hotel or flight?
Certainly — bundle your car, flight and hotel into a Windsor vacation package and you'll save a ton. With so much to uncover in the Windsor area, that set of wheels will make exploring a joy. Once you've slid into the driver's seat, get out on the wide open road and cruise toward Wrigley Field, a top sight around 120 mi from Windsor.
Which airport is best for Windsor?
The most convenient airport for Windsor is Dane County Regional Airport (MSN). You'll find it 6 mi north of the city center.
What is there to do in Windsor?
Mousehouse Cheesehaus should be on your travel schedule. After you've checked off this top attraction, simply stroll the streets of Windsor and get a feel for what makes this fantastic destination tick.

Photos of local treasures

Browse Windsor vacation photos for more inspiration

silhouette of horse statue - windsor
Windsor