Deals on vacations and trips to Windsor

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Windsor flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Valued Stay Aloha

Valued Stay Aloha

2 out of 5
Carpenter Ridgeway
Price was $423, price is now $386 per person
$386
per person
Nov 22 - Nov 24
found 10 hours ago
Roundtrip non-stop flight included
Raleigh (RDU) to Madison (MSN)
This motel features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning. Express check-in and express check-out are also provided.
Madison Marriott South

Madison Marriott South

3.5 out of 5
Price was $459, price is now $410 per person
$410
per person
Nov 22 - Nov 24
found 10 hours ago
Roundtrip non-stop flight included
Raleigh (RDU) to Madison (MSN)
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.
Fairfield by Marriott Inn & Suites Madison South

Fairfield by Marriott Inn & Suites Madison South

3 out of 5
Price was $454, price is now $406 per person
$406
per person
Nov 22 - Nov 24
found 10 hours ago
Roundtrip non-stop flight included
Raleigh (RDU) 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 $483, price is now $436 per person
$436
per person
Nov 22 - Nov 24
found 10 hours ago
Roundtrip non-stop flight included
Raleigh (RDU) 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.
The Edgewater

The Edgewater

4.5 out of 5
Downtown Madison
Price was $571, price is now $518 per person
$518
per person
Nov 22 - Nov 24
found 10 hours ago
Roundtrip non-stop flight included
Raleigh (RDU) to Madison (MSN)
A full-service spa, a hot tub, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, express check-in, and free airport shuttle. Unwind with a drink at one of the 4 bars/lounges and enjoy perks like a free area shuttle.

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
$66 nightly
The price is $70 total per night
$70 total
Oct 11 - Oct 12
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
$150 nightly
The price is $173 total per night
$173 total
Oct 25 - Oct 26
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
$139 nightly
The price is $161 total per night
$161 total
Oct 4 - Oct 5
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
Motel 6 Madison, WI - East

Motel 6 Madison, WI - East

2 out of 5
4202 E Towne Blvd Madison WI
Free Cancellation
Reserve now, pay when you stay
$50 nightly
The price is $58 total per night
$58 total
Oct 4 - Oct 5
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Express check-in, express check-out, and laundry facilities are also on offer.
Pet friendly
Parking included
AmericInn by Wyndham Madison West

AmericInn by Wyndham Madison West

3 out of 5
516 Grand Canyon Dr Madison WI
Free Cancellation
Reserve now, pay when you stay
$72 nightly
The price is $83 total per night
$83 total
Oct 4 - Oct 5
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like full breakfast and free self parking.
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
$59 nightly
The price is $68 total per night
$68 total
Oct 19 - Oct 20
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
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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.

Stay near popular Windsor attractions

Mousehouse Cheesehaus

9.0/10 (12 reviews)
Enjoy an outing to Mousehouse Cheesehaus during your stay in Windsor. Wander the area's lakeside or simply enjoy one of its top-notch restaurants.
See properties

Frequently asked questions

How much are vacation packages to Windsor?
Travelocity provides flight and hotel vacation packages starting from just $386. 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

A park with a statue of a figure on horseback, surrounded by leafless trees and a clear sky.
A building with a large rabbit mascot and signs for 'Gifts Cheese' and 'Cheese Beer'.