Deals on vacations and trips to Windsor

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Windsor flight + hotel vacation packages

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avid Hotel Wisconsin Dells – Lake Delton by IHG

avid Hotel Wisconsin Dells – Lake Delton by IHG

2.5 out of 5
Price was $541, price is now $469 per person
$469
per person
Aug 8 - Aug 13
found 1 day ago
Roundtrip flight included
New York (NYC) to Madison (MSN)
This hotel features free WiFi in public areas, a computer station, and laundry facilities. Enjoy the free continental breakfast each morning. Staff at the 24-hour front desk can provide around-the-clock assistance.
Hilton Vacation Club Christmas Mountain Village

Hilton Vacation Club Christmas Mountain Village

3 out of 5
Save 100% on your flight
Price was $1,011, price is now $806 per person
$806
per person
Aug 8 - Aug 13
found 1 day ago
Roundtrip flight included
New York (NYC) to Madison (MSN)
A golf course and an indoor pool are featured at this smoke-free resort. Take advantage of ski lessons, ski rentals and ski passes on site, and enjoy downhill skiing. There's fun for all ages with mini golf and a children's pool, and families will appreciate the onsite laundry facilities.
Holiday Inn Express and Suites-Platteville by IHG

Holiday Inn Express and Suites-Platteville by IHG

2.5 out of 5
Price was $620, price is now $534 per person
$534
per person
Aug 8 - Aug 13
found 1 day ago
Roundtrip flight included
New York (NYC) 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 buffet breakfast and free self parking.
Hilton Garden Inn Madison Downtown

Hilton Garden Inn Madison Downtown

3 out of 5
Downtown Madison
Price was $838, price is now $759 per person
$759
per person
Jul 23 - Jul 26
found 15 hours ago
Roundtrip flight included
New York (NYC) to Madison (MSN)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a coffee shop, and a snack bar/deli are also offered.

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 7 - Jun 8
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
Baymont by Wyndham Madison West/Middleton WI West

Baymont by Wyndham Madison West/Middleton WI West

2.5 out of 5
8102 Excelsior Dr Madison WI
Free Cancellation
Reserve now, pay when you stay
$61 nightly
The price is $71 total per night
$71 total
Jun 9 - Jun 10
Total with taxes and fees
This hotel features an indoor pool and a gym. Families will appreciate the arcade/game room and barbecue grills. Enjoy the hot tub and free perks like continental breakfast and free self parking.
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 7 - Jun 8
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
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
$118 nightly
The price is $136 total per night
$136 total
Jun 28 - Jun 29
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
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
$135 nightly
The price is $156 total per night
$156 total
Jun 7 - Jun 8
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
Don't see what you're looking for?
See all available properties in Windsor
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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.

Popular places to visit

University of Wisconsin-Madison

University of Wisconsin-Madison

Enjoy the collegiate vibe around University of Wisconsin-Madison, a top college in Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

University of Wisconsin-Madison
Historic Arched Entry to Camp Randall Stadium

Camp Randall Stadium

Catch an event at Camp Randall Stadium during your trip to Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Camp Randall Stadium
Capitol Square

Capitol Square

You can find out about the history of Madison with a visit to Capitol Square. Visit the area's shops, or simply enjoy its restaurants.

Capitol Square

Frequently asked questions

How much are vacation packages to Windsor?
Travelocity provides flight and hotel vacation packages starting from just $469. 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