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.
Motel 6 Janesville, WI
Price was $143, price is now $132 per person
$132
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip flight included
Miami (MIA) 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.
Bluegreen Odyssey Dells
Lake Delton
Price was $860, price is now $741 per person
$741
per person
Feb 5 - Feb 8
found 24 hours ago
Roundtrip non-stop flight included
Grand Island (GRI) to Madison (MSN)
Free water park access and a gym are featured at this smoke-free condo. Families will appreciate the waterslide and onsite laundry facilities. The front desk is staffed around-the-clock and concierge services are on offer.
Baymont Inn & Suites by Wyndham Madison
Leopold
Price was $807, price is now $720 per person
$720
per person
Feb 5 - Feb 8
found 24 hours ago
Roundtrip non-stop flight included
Grand Island (GRI) to Madison (MSN)
This hotel features an indoor pool and a gym. Relax with a drink at the bar/lounge and enjoy free perks like full breakfast and free self parking. A business center, free WiFi in public areas, and a lobby fireplace are also on offer.
The Edgewater
Downtown Madison
Price was $927, price is now $849 per person
$849
per person
Feb 5 - Feb 8
found 24 hours ago
Roundtrip non-stop flight included
Grand Island (GRI) 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.
Valued Stay Aloha
Carpenter Ridgeway
Price was $653, price is now $606 per person
$606
per person
Feb 5 - Feb 8
found 24 hours ago
Roundtrip non-stop flight included
Grand Island (GRI) 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.
Top Windsor hotels deals
Days Inn by Wyndham Madison NE/Windsor
6311 Rostad Dr Windsor WI
Free Cancellation
Reserve now, pay when you stay
$62 nightly
The price is $65 total per night
$65 total
Dec 28 - Dec 29
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
Super 8 by Wyndham Windsor/Madison North
4506 Lake Circle Windsor WI
Free Cancellation
Reserve now, pay when you stay
$65 nightly
The price is $73 total per night
$73 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.
Pet friendly
Parking included
The Madison Concourse Hotel and Governor's Club
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
Dec 28 - Dec 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 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
DoubleTree by Hilton Madison East
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
Dec 27 - Dec 28
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.
Hampton Inn & Suites Madison-West
483 Commerce Dr Madison WI
Free Cancellation
Reserve now, pay when you stay
$71 nightly
The price is $82 total per night
$82 total
Jan 9 - Jan 10, 2026
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.
The Edgewater
1001 Wisconsin Place Madison WI
Free Cancellation
Reserve now, pay when you stay
$221 nightly
The price is $255 total per night
$255 total
Dec 26 - Dec 27
Total with taxes and fees
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.
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
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.
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.
Monona Terrace Community and Convention Center
Learn about the events happening at Monona Terrace Community and Convention Center during your trip to Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
Frequently asked questions
Photos of local treasures
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