The Best Family Hotels in Windsor, WI from NT$2,071 in 2026

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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

Windsor

Let your family splash into smiles with an indoor pool, hot tub, and fitness center just minutes from Sun Prairie Aquatic Center.

NT$2,186 total

includes taxes & fees

Dec 8 - Dec 9

A hotel room with a bed, desk, chair, and a large painting on the wall.

2. Super 8 by Wyndham Windsor/Madison North

Windsor

NT$2,735 total

includes taxes & fees

Nov 15 - Nov 16

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

De Forest

NT$3,303 total

includes taxes & fees

Dec 6 - Dec 7

An indoor swimming pool with a fountain, lounge chairs, and a sunshade.

4. Comfort Inn & Suites Madison North

De Forest

Family-friendly retreat with an indoor pool paradise and hot tub for relaxation after a day of splashing with the kids.

NT$3,028 total

includes taxes & fees

Nov 29 - Nov 30

A spacious lobby with a high ceiling, a large chandelier, and a reception desk.

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

Madison

Family vacation adventures with an indoor pool and midnight hot tub relaxation in Madison's stylish hotel suburb.

NT$3,039 total

includes taxes & fees

Nov 9 - Nov 10

A multi-story hotel with a prominent 'CAMBRIA' sign, featuring a brick facade, large windows, and a covered entrance area.

6. Cambria Hotel Madison East

Madison

NT$2,878 total

includes taxes & fees

Nov 29 - Nov 30

A spacious lobby with a high ceiling, a reception desk, and a display of various items on the wall.

7. DoubleTree by Hilton Madison East

Greater Sandburg

Family vacation fun with heated indoor pool and prime location near botanical gardens.

NT$3,712 total

includes taxes & fees

Dec 6 - Dec 7

An indoor swimming pool with multiple lounge chairs and a sign indicating no lifeguard on duty.

8. Fairfield Inn & Suites by Marriott Madison East

Madison

NT$3,381 total

includes taxes & fees

Nov 30 - Dec 1

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

Madison

NT$2,549 total

includes taxes & fees

Dec 6 - Dec 7

A restaurant setting with round tables, chairs, and empty wine glasses.

10. Best Western Plus InnTowner Madison

Regent

NT$3,961 total

includes taxes & fees

Dec 6 - Dec 7

View all properties

Choose what matters most at family-friendly hotels in Windsor

Breakfast included

Pool

Top Windsor Hotel Reviews

Days Inn by Wyndham Madison NE/Windsor

Windsor

10/10 Excellent

Joanne

Holiday Inn Express Deforest (Madison Area) by IHG

De Forest

10/10 Excellent

Dale

A swimming pool with a view of a road and buildings outside.

Holiday Inn Express & Suites Madison by IHG

Madison

10/10 Excellent

April

Comfort Inn & Suites Madison North

De Forest

10/10 Excellent

Anonymous traveler

A Holiday Inn Express & Suites hotel with a brick facade, multiple windows, and a well-lit entrance.

Holiday Inn Express & Suites Madison Central by IHG

Madison

10/10 Excellent

Lisa

DoubleTree by Hilton Madison East

Greater Sandburg

10/10 Excellent

Troy

Fairfield Inn & Suites by Marriott Madison East

Madison

10/10 Excellent

Tri

A hotel room with a view of a cityscape, including a prominent dome building.

DoubleTree by Hilton Madison Downtown

Downtown Madison

10/10 Excellent

Anonymous traveler

A spacious lobby with a high ceiling, a reception desk, seating area, and a TV screen.

Hilton Garden Inn Madison Sun Prairie

Sun Prairie

10/10 Excellent

Leann

A waterfront hotel with outdoor seating and a view of the sunset over the water.

The Edgewater

Downtown Madison

10/10 Excellent

Elizabeth

Cambria Hotel Madison East

Madison

10/10 Excellent

Kathleen

A hotel entrance with a modern design, illuminated signage, and a clear view of the street.

Hyatt Place Madison Downtown

Downtown Madison

10/10 Excellent

Leticia

A cozy living area with a fireplace, comfortable seating, and decorative shelves.

Homewood Suites by Hilton Madison West

Madison

10/10 Excellent

Timothy

A spacious dining area with modern furniture and a large TV screen.

Comfort Suites Cottage Grove – Madison

Village of Cottage Grove

10/10 Excellent

This was probably the nicest hotel I have stayed at during my travels. It was as nice as some resorts I have been to. The room was spacious, modern, clean, and surprisingly quiet considering I had a room right on the balcony above the front desk. However, the thing that made this stay as good as it was, is hands down do to the staff. Every single one of them was friendly, efficient, courteous and helpful. I mostly interacted with Sofiia at the front desk, and she was wonderful. The young lady...

Malcolm

An outdoor patio area with wicker furniture, a central fire pit, and a building with a brick facade in the background.

Courtyard by Marriott Madison East

Madison

10/10 Excellent

Anonymous traveler

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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Find Family Hotels in Windsor, WI

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windsor family-friendly hotels

1. Days Inn by Wyndham Madison NE/Windsor

2. Super 8 by Wyndham Windsor/Madison North

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

4. Comfort Inn & Suites Madison North

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

6. Cambria Hotel Madison East

7. DoubleTree by Hilton Madison East

8. Fairfield Inn & Suites by Marriott Madison East

9. Holiday Inn Madison at The American Center by IHG

10. Best Western Plus InnTowner Madison

Choose what matters most at family-friendly hotels in Windsor

Top Windsor Hotel Reviews

Days Inn by Wyndham Madison NE/Windsor

10/10 Excellent

Frequently Asked Questions

What's Windsor like for family-friendly vacations?

What's the best place to stay for a family vacation to Windsor?

When’s the best time to book a family-friendly vacation in Windsor?

What's there to see and do with your family in Windsor?

Explore a world of travel with Expedia