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

Tonight
Oct 16 - Oct 17
Tomorrow
Oct 17 - Oct 18
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Windsor family-friendly hotels

An indoor swimming pool with clear blue water, surrounded by lounge chairs and a table.
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.
A modern bathroom with a white bathtub, shower, and sink.

1. Days Inn by Wyndham Madison NE/Windsor

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$2,078
NT$2,192 total
includes taxes & fees
Nov 1 - Nov 2
Days Inn by Wyndham Madison NE/Windsor
A hotel room with a bed, desk, chair, and a large painting on the wall.
A Whirlpool washer and dryer set in a laundry room with a Pepsi sign on the wall.
A bathroom with a white bathtub, a toilet, and a shower curtain.
A motel with a Super 8 sign and a Topp's Mideaway sign.

2. Super 8 by Wyndham Windsor/Madison North

Super 8 by Wyndham Windsor/Madison North
Windsor
NT$2,027
NT$2,280 total
includes taxes & fees
Oct 29 - Oct 30
Super 8 by Wyndham Windsor/Madison North
A modern hotel room with a bed, a desk, a chair, and a sofa.
An indoor swimming pool with blue and white tiled walls, a clear pool, and lounge chairs along the sides.
A modern hotel room with a wooden desk, an orange chair, a flat-screen TV, and a wall-mounted mirror.
A compact hotel bathroom with a sink, mirror, and a small refrigerator.

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

Holiday Inn Express Deforest (Madison Area) by IHG
De Forest
NT$2,949
NT$3,259 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express Deforest (Madison Area) by IHG
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 lobby with a staircase, blue sofa, red chairs, a fireplace, and a reception desk.

4. Comfort Inn & Suites Madison North

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$2,696
NT$2,979 total
includes taxes & fees
Nov 8 - Nov 9
Comfort Inn & Suites Madison North
A spacious lobby with a high ceiling, a reception desk, and a display of various items on the wall.
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.
An indoor swimming pool with clear markings for non-diving and diving areas, surrounded by lounge chairs and tables.
A modern building with a glass facade, a covered entrance, and a flagpole.

5. DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East
Greater Sandburg
  • Family vacation fun with heated indoor pool and prime location near botanical gardens.
NT$3,403
NT$3,930 total
includes taxes & fees
Oct 31 - Nov 1
DoubleTree by Hilton Madison East
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.
An indoor swimming pool with clear glass ceilings, lounge chairs, and a view of the outdoors.
A lobby with a fireplace, two armchairs, and two small tables.

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

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$2,577
NT$2,976 total
includes taxes & fees
Nov 1 - Nov 2
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.
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.
A modern bar area with a long counter, bar stools, and a television mounted above the bar.

7. Cambria Hotel Madison East

Cambria Hotel Madison East
Madison
NT$2,707
NT$3,127 total
includes taxes & fees
Nov 9 - Nov 10
Cambria Hotel Madison East
An indoor swimming pool with multiple lounge chairs and a sign indicating no lifeguard on duty.
A spacious lobby with a fireplace, seating area, and a bar.
A hotel room with a bed, a desk with a telephone, a television on a wooden stand, and a small plant.
A hotel lobby with multiple seating areas, a bar, and a fireplace.

8. Fairfield Inn & Suites by Marriott Madison East

Fairfield Inn & Suites by Marriott Madison East
Madison
NT$3,156
NT$3,645 total
includes taxes & fees
Oct 29 - Oct 30
Fairfield Inn & Suites by Marriott Madison East
An indoor swimming pool with a basketball hoop, lounge chairs, and a palm tree decoration.
A bathroom with a black countertop, white sink, and a white toilet. There is a framed picture on the wall and a glass shower enclosure.
A Holiday Inn hotel with a glass entrance canopy, brick facade, and green lighting.
A hotel corridor with striped chairs, potted plants, and a framed picture on the wall.

9. Holiday Inn Madison at The American Center by IHG

Holiday Inn Madison at The American Center by IHG
Madison
NT$2,301
NT$2,657 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Madison at The American Center by IHG
A hotel room with a view of a cityscape, including a prominent dome building.
A conference room with a long table, chairs, and a carpeted floor.
A spacious lobby with seating areas, a reception desk, and a glass door entrance.
A gym with treadmills, elliptical machines, and exercise balls.

10. DoubleTree by Hilton Madison Downtown

DoubleTree by Hilton Madison Downtown
Downtown Madison
NT$4,074
NT$4,706 total
includes taxes & fees
Nov 8 - Nov 9
DoubleTree by Hilton Madison Downtown
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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

The Madison Concourse Hotel and Governor's Club

10/10 Excellent
"Clean rooms, attentive staff, fantastic Governers Club perks, and perfect location."
Davin 1-night trip
Posted 10 hours ago
The Madison Concourse Hotel and Governor's Club
Best Western Premier Park Hotel

Best Western Premier Park Hotel

8/10 Good
"We had a great stay overall and would definitely return! We stayed in the two-room King Suite with a balcony, and the room was spacious, comfortable, and well-appointed. Having the extra living space made the suite feel roomy and accommodating, and the balcony was a nice added feature. The room met our expectations in terms of layout and amenities. My only real concerns were the mattress, which could have been more comfortable, and the pillows, which were rather lumpy and could use replacing. The mattress was extremely firm. A little improvement in the bedding would make an already great room even better. Overall, we enjoyed our stay and were very pleased with the accommodations. Despite the minor issues with the mattress and pillows, I would happily stay here again and would recommend it to others!"
jeremy 1-night trip
Posted 18 hours ago
Best Western Premier Park Hotel
DoubleTree by Hilton Madison Downtown

DoubleTree by Hilton Madison Downtown

10/10 Excellent
"Friendly staff, great breakfast and the rooms were in great shape. Would stay again if I visit Madison again."
Spencer 2-night trip
Posted 2 days ago
DoubleTree by Hilton Madison Downtown
Hampton Inn & Suites Madison-West

Hampton Inn & Suites Madison-West

10/10 Excellent
"Parking is nice. Clean room and facility"
Scott 2-night trip
Posted 3 days ago
Hampton Inn & Suites Madison-West

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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