Family friendly Hotels, Windsor Madison

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

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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.

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

A modern bathroom with a white bathtub, shower, and sink.

A Days Inn hotel with a covered entrance, brick pillars, and a parking lot.

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.

P3,988

P4,207 total

includes taxes & fees

Oct 11 - Oct 12

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

A motel with a Super 8 sign and a Topp's Mideaway sign.

A bathroom with a white bathtub, a toilet, and a shower curtain.

A Whirlpool washer and dryer set in a laundry room with a Pepsi sign on the wall.

2. Super 8 by Wyndham Windsor/Madison North

Windsor

P4,222

P4,751 total

includes taxes & fees

Oct 4 - Oct 5

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

A hotel room with a sofa, ottoman, desk, lamp, TV, and a large window with curtains.

A hotel room with a blue sofa, a brown ottoman, a white bathtub, and a large mirror.

A hotel room with a bed, a blue sofa, two small tables, a lamp, and two framed pictures on the wall.

3. 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.

P5,244

P5,795 total

includes taxes & fees

Nov 1 - Nov 2

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

An indoor swimming pool with clear glass ceilings, lounge chairs, and a view of the outdoors.

A modern hotel room with a large bed, a separate bathroom with a bathtub, and a blue accent wall.

A hotel room with a flat-screen TV mounted on the wall, a kitchenette with a microwave and refrigerator, a desk with a chair, and a green upholstered chair.

4. 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.

P5,010

P5,787 total

includes taxes & fees

Oct 4 - Oct 5

A hotel room with two beds, a desk, a chair, a flat-screen TV, and a window with a view.

A coffee station with two espresso machines, a coffee grinder, and various coffee-related items.

A modern kitchen area with a coffee station, a chalkboard menu, and a buffet counter with food displays.

A conference room with tables and chairs, a carpeted floor, and framed artwork on the wall.

5. Holiday Inn Express & Suites Madison by IHG

Madison

P6,943

P8,019 total

includes taxes & fees

Nov 1 - Nov 2

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

A spacious lobby with a stone wall, large windows, and comfortable seating areas.

An outdoor patio with tables and chairs, large windows, and a view of the surrounding greenery.

An indoor swimming pool with clear depth markings, safety signs, and a lifeguard on duty.

6. Cambria Hotel Madison East

Madison

P5,264

P6,080 total

includes taxes & fees

Nov 1 - Nov 2

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

A modern building with a glass facade, a covered entrance, and a flagpole.

An indoor swimming pool with clear markings for non-diving and diving areas, surrounded by lounge chairs and tables.

A hotel room with a grey sofa, a small ottoman, a desk with a mirror, a flat-screen TV, and a cityscape artwork on the wall.

7. DoubleTree by Hilton Madison East

Greater Sandburg

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

P6,617

P7,642 total

includes taxes & fees

Nov 1 - Nov 2

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

A gym with various exercise equipment, a wall-mounted TV, and a large window providing natural light.

A bar area with a long counter, multiple bar stools, and a variety of bottles and glasses.

A spacious dining area with a long table and multiple chairs, a bar area with stools, and a seating area with cushioned booths.

8. DoubleTree by Hilton Madison Downtown

Downtown Madison

P7,643

P8,827 total

includes taxes & fees

Nov 1 - Nov 2

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Choose what matters most at family-friendly hotels in Windsor

Breakfast included

Pool

All-inclusive

4 stars

5 stars

Top Windsor Hotel Reviews

Best Western Plus InnTowner Madison

10/10 Excellent

"Very clean, well maintained, and staffed by genuinely friendly people. Breakfast was included, parking was free, and the complimentary shuttle will take you anywhere within two miles until 10:30 p.m.—perfect for getting to the UW Field House for a women’s volleyball game. The hotel also has a nice fitness room, hot tub, and warm pool, plus an on-site restaurant and drinks. With its great location and thoughtful amenities, this place was truly impressive."

La Quinta Inn & Suites by Wyndham Madison American Center

10/10 Excellent

"Entire staff was very friendly. Room very clean except for a lot of dust under furniture which my dog found. Good breakfast."

Super 8 by Wyndham Madison South

8/10 Good

"X"

The Madison Concourse Hotel and Governor's Club

10/10 Excellent

"Outstanding location and property. My wife and I will be returning for certain!"

Comfort Suites Madison West - Middleton

8/10 Good

"The breakfast was not ready on time. All utensils in the breakfast area were covered in dust. The coffee was also poorly made"

DoubleTree by Hilton Madison East

10/10 Excellent

"Great spot for quick stay-overs! Reasonable and convenient to our needs!"

Baymont by Wyndham Madison West/Middleton WI West

10/10 Excellent

"The property was clean and the building was cleaned regularly."

The Edgewater

10/10 Excellent

"The Edgewater is one of my favorite hotels. I had such a wonderful stay and always enjoy being here. I’ll definitely be back!"

Hampton Inn & Suites Madison-West

10/10 Excellent

"As always terrific staff and great rooms."

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.

Room 1

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Check availability on Windsor Family friendly Hotels

Our top choices for Windsor family-friendly hotels

1. Days Inn by Wyndham Madison NE/Windsor