Search Deals onWindsor Vacation Packages
Windsor Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Club Wyndham Tamarack
Price was $611, price is now $506 per person
$506
per person
Oct 22 - Oct 25
found 22 hours ago
Roundtrip flight included
Chicago (ORD) to Madison (MSN)
Stay at this hotel in Wisconsin Dells. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Noah's Ark Waterpark and Mt. Olympus Water and Theme Park are located nearby.
The room was spotless and it was nice to relax with the fireplace. Also enjoyed saving money by buying and cooking our own meals.
Reviewed on May 12, 2026
Graduate by Hilton Madison
Price was $3,052, price is now $2,336 per person
$2,336
per person
Nov 2 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Madison (MSN)
Book a stay at this business-friendly hotel in Madison. Enjoy a rooftop terrace, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Capitol Square and Camp Randall Stadium are located nearby.
Restaurant was not open on the one night we stayed and they had a small coffee shop. It’s a smaller lobby and public areas than a normal graduate hotel.
Reviewed on Aug 24, 2026
The Madison Concourse Hotel and Governor's Club
Price was $2,591, price is now $2,139 per person
$2,139
per person
Nov 2 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Madison (MSN)
Book a stay at this luxury hotel in Madison. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the pool in our reviews. Popular attractions Capitol Square and Camp Randall Stadium are located nearby.
H
Reviewed on Aug 27, 2026
Madison Marriott South
Price was $1,950, price is now $1,629 per person
$1,629
per person
Nov 2 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Madison (MSN)
Book a stay at this business-friendly hotel in Madison. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Alliant Energy Center and Capitol Square are located nearby.
The room was clean and bed was comfortable. Overall a great experience.
Reviewed on Aug 26, 2026
Dellshire Resort
Price was $689, price is now $576 per person
$576
per person
Oct 22 - Oct 25
found 22 hours ago
Roundtrip flight included
Chicago (ORD) to Madison (MSN)
Book a stay at this family-friendly hotel in Wisconsin Dells. Enjoy free WiFi, free parking, and 3 indoor pools. Popular attractions Mt. Olympus Water and Theme Park and Noah's Ark Waterpark are located nearby.
Hilton Madison Monona Terrace
Price was $2,388, price is now $2,063 per person
$2,063
per person
Nov 2 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Madison (MSN)
Book a stay at this business-friendly hotel in Madison. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Capitol Square and Camp Randall Stadium are located nearby.
Valued Stay Aloha
Price was $1,567, price is now $1,364 per person
$1,364
per person
Nov 2 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Madison (MSN)
Stay at this motel in Madison. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions East Towne Mall and Capitol Square are located nearby.
Courtyard by Marriott Madison East
Price was $1,870, price is now $1,631 per person
$1,631
per person
Nov 2 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Madison (MSN)
Book a stay at this business-friendly hotel in Madison. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions East Towne Mall and Capitol Square are located nearby.
Windsor Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Windsor Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, Nov 10 - Sat, Nov 14
MSP
Minneapolis - St. Paul Intl.
MSN
Dane County Regional
$206 Roundtrip, found 2 hours ago
$206
Roundtrip
found 2 hours ago
Fri, Oct 30 - Fri, Nov 13
ATL
Hartsfield-Jackson Atlanta Intl.
MSN
Dane County Regional
$247 Roundtrip, found 1 hour ago
$247
Roundtrip
found 1 hour ago
Sat, Nov 14 - Mon, Nov 16
BOS
Logan Intl.
MSN
Dane County Regional
$263 Roundtrip, found 2 hours ago
$263
Roundtrip
found 2 hours ago
Tue, Oct 20 - Tue, Oct 27
DCA
Ronald Reagan Washington National
MSN
Dane County Regional
$268 Roundtrip, found 2 days ago
$268
Roundtrip
found 2 days ago
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