Deals on vacations and trips to Windsor

Save when you book Windsor package deals

Choose two or more items and save on your trip:

Windsor flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Motel 6 Janesville, WI

Motel 6 Janesville, WI

2 out of 5
Price was $210, price is now $199 per person
$199
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Madison (MSN)
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A snack bar/deli and laundry facilities are also provided.
Hampton Inn Janesville

Hampton Inn Janesville

2.5 out of 5
Price was $448, price is now $431 per person
$431
per person
Mar 19 - Mar 22
found 18 hours ago
Roundtrip flight included
Orlando (MCO) to Madison (MSN)
This hotel features an indoor pool and a gym. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A business center, a grocery/convenience store, and express check-in are also on offer.
TownePlace Suites by Marriott Janesville

TownePlace Suites by Marriott Janesville

3 out of 5
Price was $285, price is now $281 per person
$281
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Madison (MSN)
This hotel features an indoor pool and a gym. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. Guests will appreciate freebies like continental breakfast and free self parking.

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
$62 nightly
The price is $65 total per night
$65 total
Jan 18 - Jan 19
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
Jan 18 - Jan 19
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
Hampton Inn & Suites Madison-West

Hampton Inn & Suites Madison-West

2.5 out of 5
483 Commerce Dr Madison WI
Free Cancellation
Reserve now, pay when you stay
$73 nightly
The price is $84 total per night
$84 total
Feb 1 - Feb 2
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the hot tub and free perks like buffet 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
$106 nightly
The price is $122 total per night
$122 total
Jan 15 - Jan 16
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
$69 nightly
The price is $80 total per night
$80 total
Jan 20 - Jan 21
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
La Quinta Inn & Suites by Wyndham Madison American Center

La Quinta Inn & Suites by Wyndham Madison American Center

3 out of 5
5217 E Terrace Dr Madison WI
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $87 total per night
$87 total
Jan 18 - Jan 19
Total with taxes and fees
This hotel features an indoor pool and a gym. Enjoy the hot tub and free perks like continental breakfast and free self parking. A 24-hour business center, a lobby fireplace, and a communal living room are also on offer.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Windsor
View all properties
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

Cool street art in Madison, Wisconsin

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
This is great focal point for Madison!

Wisconsin State Capitol

After visiting Wisconsin State Capitol, make a plan to see the other sights and activities in Madison. Discover the area's top-notch restaurants and its entertainment choices.

Wisconsin State Capitol
Capitol Building

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 $199. 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

Right off the highway, Mousehouse is a must visit for a quirky and fun stop that rewards visitors with delicious cheese and local brews.
Right off the highway, Mousehouse is a must visit for a quirky and fun stop that rewards visitors with delicious cheese and local brews.