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 Hotels

This weekend
Nov 6 - Nov 8
Next weekend
Nov 13 - Nov 15

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, (1,006 reviews)
"Great stay"
United States
TARA
The price is NT$2,105
NT$2,221 total
includes taxes & fees
Dec 3 - Dec 4
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)
"Quite clean room! Helpful staff."
United States
Oswaldo
The price is NT$2,412
NT$2,714 total
includes taxes & fees
Nov 15 - Nov 16
Super 8 by Wyndham Windsor/Madison North
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

Best Western Plus InnTowner Madison

Best Western Plus InnTowner Madison

10/10 Excellent
"I really enjoyed this place! The attached restaurant was great for quick dinner accommodations. Great location too!"
Corey 2-night trip
Posted 5 hours ago
Best Western Plus InnTowner Madison
Cambria Hotel Madison East

Cambria Hotel Madison East

10/10 Excellent
"This was a wonderful choice for my recent trip. I had been in Tokyo for a couple of weeks, helping my son get packed up, and we needed a spot to stay for the last three nights, after he had vacated his apartment. The room was very clean, and the beds were comfortable. The dedk manager was very helpful, friendly, and spoke excellent English. My only suggestion is that it would be nice to have a privacy curtain between the bedroom and the bath area. It would not matter for a married couple, but my son and I needed to work around the shower room set up, because there was no private changing area outside of it."
Linda 1-night trip
Posted 11 hours ago
Cambria Hotel Madison East

Frequently asked questions

What's Windsor like for family-friendly vacations?
If you've been thinking about a trip with your kids, the budget-friendly destination of Windsor is a good choice. The golfing, sporting events, and cheese shops are just some of the things that make this an attractive family vacation spot. Take to the air and fly into Dane County Regional Airport (MSN), which is located 5.6 mi (9.1 km) from the city center.
What's the best place to stay for a family vacation to 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 vacation in Windsor?
The hottest months are usually July and August with an average temp of 68°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Windsor are January, December, March, and November, with each month seeing an average of 9 inches of snowfall.
What's there to see and do with your family in Windsor?
While you and your family are staying in Windsor, you might want to visit some family-friendly attractions such as Mousehouse Cheesehaus, East Towne Mall, and Barrymore Theatre. Make sure you have lots of time for activities like Breese Stevens Field and Orpheum Theater.

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