TOP Family-Friendly Hotels in Windsor, WI for 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.

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

A living room with a red sofa, patterned chairs, a glass coffee table, and a fireplace.

1. Days Inn by Wyndham Madison NE/Windsor

Windsor

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

Rp1.164.221

Rp1.228.253 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

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

2. Super 8 by Wyndham Windsor/Madison North

Windsor

Rp1.133.496

Rp1.275.273 total

includes taxes & fees

29 Oct - 30 Oct

A modern hotel room with a bed, a desk, a chair, and a sofa.

A modern room with a blue wall, a wooden desk, a yellow office chair, a blue sofa, and a floor lamp.

A compact hotel bathroom with a sink, mirror, and a small refrigerator.

An indoor swimming pool with blue and white tiled walls, a clear pool, and lounge chairs along the sides.

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

De Forest

Rp1.567.914

Rp1.732.544 total

includes taxes & fees

22 Nov - 23 Nov

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

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.

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

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.

Rp1.499.430

Rp1.656.871 total

includes taxes & fees

15 Nov - 16 Nov

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.

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.

A spacious lobby with a bar area, seating arrangements, and a decorative partition.

5. DoubleTree by Hilton Madison East

Greater Sandburg

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

Rp1.903.194

Rp2.198.189 total

includes taxes & fees

31 Oct - 1 Nov

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

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.

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

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

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

Madison

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

Rp1.441.159

Rp1.664.539 total

includes taxes & fees

1 Nov - 2 Nov

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.

A modern bar area with a long counter, bar stools, and a television mounted above the bar.

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

7. Cambria Hotel Madison East

Madison

Rp1.516.551

Rp1.751.617 total

includes taxes & fees

12 Nov - 13 Nov

An indoor swimming pool with a basketball hoop, lounge chairs, and a palm tree decoration.

A hotel corridor with striped chairs, potted plants, and a framed picture on the wall.

A breakfast setting with two plates of eggs, bacon, and toast, a bowl of fruit, and a glass of orange juice.

A Holiday Inn hotel with a glass entrance canopy, brick facade, and green lighting.

8. Holiday Inn Madison at The American Center by IHG

Madison

Rp1.279.562

Rp1.477.894 total

includes taxes & fees

22 Nov - 23 Nov

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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

The Madison Concourse Hotel and Governor's Club

8/10 Good

"It’s downtown. Easy to walk to either lake."

Best Western Premier Park Hotel

10/10 Excellent

"Have stayed there before it’s always nice"

DoubleTree by Hilton Madison East

10/10 Excellent

"Great property and helpful staff."

AmericInn by Wyndham Madison West

10/10 Excellent

"Very clean hotel. The staff were very nice and helpful. The breakfast was awesome! Will start again when we have to go back down to UW Madison hospital."

Hampton Inn & Suites Madison-West

8/10 Good

"It was clean and spacious and good for the one night we stayed. You could hear through the walls and into the hallway quite easily, so I would not want to stay here for a long period or if I knew I would be in the hotel a lot."

Baymont by Wyndham Madison West/Middleton WI West

10/10 Excellent

"It’s very clean and well served breakfast at our stay thanks and we will for sure come again."

Days Inn & Suites by Wyndham Madison

10/10 Excellent

"everything was perfect"

DoubleTree by Hilton Madison Downtown

10/10 Excellent

"The rooms are small but comfortable, and the bed and pillows are very comfortable! Location is great, front-desk staff are very friendly and helpful. The exercise gym is spacious and well-designed, looking onto a small patio. This is my second stay at this hotel and I would book it again when returning to downtown Madison."

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.

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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

2. Super 8 by Wyndham Windsor/Madison North