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Windsor Vacation Packages

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Windsor Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Beloit by IHG

Holiday Inn Express & Suites Beloit by IHG

3.5 out of 5
Price was $560, price is now $482 per person
$482
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Madison (MSN)
Book a stay at this business-friendly hotel in Beloit. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Turtle Creek Parkway and Leeson Park are located nearby.

Hilton Madison Monona Terrace

Hilton Madison Monona Terrace

4 out of 5
Price was $997, price is now $813 per person
$813
per person
Nov 25 - Nov 29
found 10 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) 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 Camp Randall Stadium and Alliant Energy Center are located nearby.

Holiday Inn Express Janesville - I-90 & US Hwy 14 by IHG

Holiday Inn Express Janesville - I-90 & US Hwy 14 by IHG

2.5 out of 5
Price was $536, price is now $485 per person
$485
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Madison (MSN)
Book a stay at this business-friendly hotel in Janesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Janesville Mall and Palmer Park Tennis Center are located nearby.

Cobblestone Hotel and Suites Janesville

Cobblestone Hotel and Suites Janesville

2.5 out of 5
Price was $706, price is now $648 per person
$648
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Madison (MSN)
Book a stay at this business-friendly hotel in Janesville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Drill Hall Theater at the Armory and Rock County Historical Society Museum are located nearby.
Squeaky bed and missing hairdryer in 312 but still a very nice stay!

Reviewed on Oct 8, 2026

1810 Emerson House Bed & Breakfast - Adults Only

1810 Emerson House Bed & Breakfast - Adults Only

3.5 out of 5
Price was $837, price is now $768 per person
$768
per person
Nov 23 - Nov 27
found 19 hours ago
Roundtrip flight included
Phoenix (PHX) to Madison (MSN)
Stay at this B&B in Beloit. Enjoy free WiFi, free parking, and a garden. Popular attractions Hancock Field and Rosevelt Park are located nearby.
Simply the BEST stay! Tony and Beth are the kindest hosts! The space is cozy and intimate; perfect for special occasions. My husband and I have had the privilege of staying here 3 times, and this will always be one of our favorite spots for a getaway! We highly recommend this gem!

Reviewed on Mar 22, 2026

AmericInn by Wyndham Madison South

AmericInn by Wyndham Madison South

3 out of 5
Price was $748, price is now $704 per person
$704
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Madison (MSN)
Book a stay at this business-friendly hotel in Madison. Enjoy free breakfast, free parking, and a sauna. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Alliant Energy Center and Camp Randall Stadium are located nearby.
My grandkids enjoyed the pool.

Reviewed on Oct 12, 2026

AmericInn by Wyndham Beloit

AmericInn by Wyndham Beloit

3 out of 5
Price was $522, price is now $494 per person
$494
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Madison (MSN)
Book a stay at this business-friendly hotel in Beloit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Turtle Creek Parkway and Leeson Park are located nearby.

Home2 Suites by Hilton Beloit

Home2 Suites by Hilton Beloit

3 out of 5
Price was $630, price is now $595 per person
$595
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Madison (MSN)
Stay at this hotel in Beloit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Turtle Creek Parkway and Leeson Park are located nearby.

Windsor Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
AmericInn by Wyndham Madison South

AmericInn by Wyndham Madison South

3 out of 5
Monona
Price was $748, price is now $704 per person
$704
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Madison (MSN)
Hilton Madison Monona Terrace

Hilton Madison Monona Terrace

4 out of 5
Downtown Madison
Price was $997, price is now $813 per person
$813
per person
Nov 25 - Nov 29
found 10 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Madison (MSN)
1810 Emerson House Bed & Breakfast - Adults Only

1810 Emerson House Bed & Breakfast - Adults Only

3.5 out of 5
Price was $837, price is now $768 per person
$768
per person
Nov 23 - Nov 27
found 19 hours ago
Roundtrip flight included
Phoenix (PHX) to Madison (MSN)
The Speckled Hen Inn B&B

The Speckled Hen Inn B&B

4 out of 5
Price was $1,060, price is now $1,009 per person
$1,009
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Madison (MSN)

Windsor Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Beloit by IHG

Holiday Inn Express & Suites Beloit by IHG

3.5 out of 5
Price was $560, price is now $482 per person
$482
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Madison (MSN)
Holiday Inn Express Janesville - I-90 & US Hwy 14 by IHG

Holiday Inn Express Janesville - I-90 & US Hwy 14 by IHG

2.5 out of 5
Price was $536, price is now $485 per person
$485
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Madison (MSN)
Cobblestone Hotel and Suites Janesville

Cobblestone Hotel and Suites Janesville

2.5 out of 5
Price was $706, price is now $648 per person
$648
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Madison (MSN)
AmericInn by Wyndham Beloit

AmericInn by Wyndham Beloit

3 out of 5
Price was $522, price is now $494 per person
$494
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Madison (MSN)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Bargain Flight
Sat, Nov 7 - Wed, Nov 11
MSP
Minneapolis - St. Paul Intl.
MSN
Dane County Regional
$228 Roundtrip, just found
$228
Roundtrip
just found
Select Bargain Flight flight, departing Sat, Nov 7 from Minneapolis - St. Paul Intl. to Dane County Regional, returning Wed, Nov 11, priced at $228 just found
Bargain Flight
Tue, Oct 20 - Tue, Oct 27
DCA
Ronald Reagan Washington National
MSN
Dane County Regional
$278 Roundtrip, found 5 hours ago
$278
Roundtrip
found 5 hours ago
Select Bargain Flight flight, departing Tue, Oct 20 from Ronald Reagan Washington National to Dane County Regional, returning Tue, Oct 27, priced at $278 found 5 hours ago
Bargain Flight
Mon, Nov 2 - Fri, Nov 13
ATL
Hartsfield-Jackson Atlanta Intl.
MSN
Dane County Regional
$286 Roundtrip, found 8 hours ago
$286
Roundtrip
found 8 hours ago
Select Bargain Flight flight, departing Mon, Nov 2 from Hartsfield-Jackson Atlanta Intl. to Dane County Regional, returning Fri, Nov 13, priced at $286 found 8 hours ago
Bargain Flight
Wed, Oct 28 - Tue, Nov 10
BOS
Logan Intl.
MSN
Dane County Regional
$288 Roundtrip, found 11 hours ago
$288
Roundtrip
found 11 hours ago
Select Bargain Flight flight, departing Wed, Oct 28 from Logan Intl. to Dane County Regional, returning Tue, Nov 10, priced at $288 found 11 hours ago