A park with a statue of a figure on horseback, surrounded by leafless trees and a clear sky.

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Check availability on Windsor Family-Friendly Hotels

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Our top choices for Windsor family-friendly hotels

An indoor swimming pool with clear blue water, surrounded by lounge chairs and a table.

1. Days Inn by Wyndham Madison NE/Windsor

Days Inn by Wyndham Madison NE/Windsor
2.0 star property
Windsor
7.2 out of 10, Good, (1,008 reviews)
  • cleanliness
    Let your family splash into smiles with an indoor pool, hot tub, and fitness centre just minutes from Sun Prairie Aquatic Centre.
The price is ฿2,212
฿2,333 total
includes taxes & fees
17 Nov - 18 Nov
Days Inn by Wyndham Madison NE/Windsor
A hotel room with a bed, desk, chair, and a large painting on the wall.

2. Super 8 by Wyndham Windsor/Madison North

Super 8 by Wyndham Windsor/Madison North
2.0 star property
Windsor
6.6 out of 10, (506 reviews)
The price is ฿2,365
฿2,661 total
includes taxes & fees
29 Oct - 30 Oct
Super 8 by Wyndham Windsor/Madison North
A buffet setup with various food items in metal containers, a patterned wall, and a counter with utensils.

3. Holiday Inn Express Deforest (Madison Area) by IHG

Holiday Inn Express Deforest (Madison Area) by IHG
2.5 star property
De Forest
8.6 out of 10, Excellent, (644 reviews)
The price is ฿3,142
฿3,473 total
includes taxes & fees
15 Nov - 16 Nov
Holiday Inn Express Deforest (Madison Area) by IHG
An indoor swimming pool with a fountain, lounge chairs, and a sunshade.

4. Comfort Inn & Suites Madison North

Comfort Inn & Suites Madison North
2.5 star property
De Forest
8.8 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Family-friendly retreat with an indoor pool paradise and hot tub for relaxation after a day of splashing with the kids.
The price is ฿2,811
฿3,107 total
includes taxes & fees
22 Nov - 23 Nov
Comfort Inn & Suites Madison North
A spacious lobby with a high ceiling, a reception desk, and a display of various items on the wall.

5. DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East
4.0 star property
Greater Sandburg
9.4 out of 10, Exceptional, (1,129 reviews)
  • cleanliness
    Family holiday fun with heated indoor pool and prime location near botanical gardens.
The price is ฿3,573
฿4,127 total
includes taxes & fees
22 Nov - 23 Nov
DoubleTree by Hilton Madison East
A spacious lobby with a high ceiling, a large chandelier, and a reception desk.

6. La Quinta Inn & Suites by Wyndham Madison American Center

La Quinta Inn & Suites by Wyndham Madison American Center
3.0 star property
Madison
8.2 out of 10, Very good, (1,425 reviews)
  • cleanliness
    Family holiday adventures with an indoor pool and midnight hot tub relaxation in Madison's stylish hotel suburb.
The price is ฿2,706
฿3,125 total
includes taxes & fees
3 Nov - 4 Nov
La Quinta Inn & Suites by Wyndham Madison American Center
A multi-story hotel with a prominent 'CAMBRIA' sign, featuring a brick facade, large windows, and a covered entrance area.

7. Cambria Hotel Madison East

Cambria Hotel Madison East
3.0 star property
Madison
8.6 out of 10, Excellent, (1,002 reviews)
The price is ฿2,699
฿3,117 total
includes taxes & fees
23 Nov - 24 Nov
Cambria Hotel Madison East
An indoor swimming pool with multiple lounge chairs and a sign indicating no lifeguard on duty.

8. Fairfield Inn & Suites by Marriott Madison East

Fairfield Inn & Suites by Marriott Madison East
3.0 star property
Madison
9.2 out of 10, Wonderful, (1,000 reviews)
The price is ฿3,162
฿3,652 total
includes taxes & fees
26 Nov - 27 Nov
Fairfield Inn & Suites by Marriott Madison East
An indoor swimming pool with a basketball hoop, lounge chairs, and a palm tree decoration.

9. Holiday Inn Madison at The American Center by IHG

Holiday Inn Madison at The American Center by IHG
3.0 star property
Madison
8.4 out of 10, Very good, (826 reviews)
The price is ฿2,533
฿2,926 total
includes taxes & fees
26 Nov - 27 Nov
Holiday Inn Madison at The American Center by IHG
A spacious lobby with a high ceiling, a reception desk, seating area, and a TV screen.

10. Hilton Garden Inn Madison Sun Prairie

Hilton Garden Inn Madison Sun Prairie
3.0 star property
Sun Prairie
9.4 out of 10, Exceptional, (393 reviews)
The price is ฿4,854
฿5,461 total
includes taxes & fees
22 Nov - 23 Nov
Hilton Garden Inn Madison Sun Prairie
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.
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Choose what matters most at family-friendly hotels in Windsor

Breakfast included
Pool

Top Windsor Hotel Reviews

AmericInn by Wyndham Madison West

AmericInn by Wyndham Madison West

10/10 Excellent
"Clean room and good breakfast"
Timothy 1-night trip
Posted less than an hour ago
AmericInn by Wyndham Madison West

Frequently asked questions

What's Windsor like for family-friendly holidays?
If you've been thinking about a trip with your children, the budget-friendly destination of Windsor is a good choice. The golf, sporting events and cheese shops are just some of the things that make this an attractive spot for a family holiday. Take to the air and fly into Dane County Regional Airport (MSN), which is located 5.6 mi (9.1 km) from the city centre.
What's the best family accommodation in Windsor?
Days Inn by Wyndham Madison NE/Windsor is a hotel with an indoor pool and free parking, and it's a top choice on Expedia for families.
When's the best time to book a family-friendly holiday in Windsor?
The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Windsor are January, December, March and November, with each month seeing an average of 22 cm of snowfall.
What's there to see and do with your family in Windsor?
While you and your family are staying in Windsor, you may want to visit some family-friendly attractions such as Mousehouse Cheesehaus, East Towne Mall and Barrymore Theatre. Make sure that you have lots of time for activities such as Breese Stevens Field and Orpheum Theater.