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 friendly Hotels

Tonight
11 Oct - 12 Oct
Tomorrow
12 Oct - 13 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

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 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 centre just minutes from Sun Prairie Aquatic Centre.
S$87
includes taxes & fees
1 Nov - 2 Nov
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 lobby with a large welcome sign, leather armchairs, a leather sofa, a clock, and a TV on a stand.
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
S$91
includes taxes & fees
29 Oct - 30 Oct
Super 8 by Wyndham Windsor/Madison North
An indoor swimming pool with a fountain, lounge chairs, and a sunshade.
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.
A lobby with a staircase, blue sofa, red chairs, a fireplace, and a reception desk.

3. 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.
S$118
includes taxes & fees
1 Nov - 2 Nov
Comfort Inn & Suites Madison North
A modern hotel room with a bed, a desk, a chair, and a sofa.
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.
A snack and beverage vending area with multiple shelves stocked with various snacks and a refrigerated section with bottled drinks.

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

Holiday Inn Express Deforest (Madison Area) by IHG
De Forest
S$134
includes taxes & fees
8 Nov - 9 Nov
Holiday Inn Express Deforest (Madison Area) by IHG
A spacious lobby with a high ceiling, a reception desk, and a display of various items on the wall.
A spacious lobby with a bar area, seating arrangements, and a decorative partition.
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.

5. DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East
Greater Sandburg
  • Family holiday fun with heated indoor pool and prime location near botanical gardens.
S$156
includes taxes & fees
1 Nov - 2 Nov
DoubleTree by Hilton Madison East
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 lobby with a fireplace, two armchairs, and two small tables.
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.

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

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.
S$118
includes taxes & fees
18 Oct - 19 Oct
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.
A spacious lobby with a stone wall, large windows, and comfortable seating areas.
An indoor swimming pool with clear depth markings, safety signs, and a lifeguard on duty.

7. Cambria Hotel Madison East

Cambria Hotel Madison East
Madison
S$124
includes taxes & fees
1 Nov - 2 Nov
Cambria Hotel Madison East
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

Holiday Inn Madison at The American Center by IHG
Madison
S$111
includes taxes & fees
9 Nov - 10 Nov
Holiday Inn Madison at The American Center by IHG
An indoor swimming pool with multiple lounge chairs and a sign indicating no lifeguard on duty.
A hotel room with a bed, a desk with a telephone, a television on a wooden stand, and a small plant.
A spacious lobby with a fireplace, seating area, and a bar.
A hotel lobby with multiple seating areas, a bar, and a fireplace.

9. Fairfield Inn & Suites by Marriott Madison East

Fairfield Inn & Suites by Marriott Madison East
Madison
S$145
includes taxes & fees
29 Oct - 30 Oct
Fairfield Inn & Suites by Marriott Madison East
A spacious lobby with a high ceiling, a reception desk, seating area, and a TV screen.
An outdoor patio area with wicker furniture, tables, and chairs.
A hotel reception area with a coffee station, a TV screen displaying a news program, and a counter with various food items.
A modern lobby with a white sofa, blue armchair, and green armchairs. There is a fireplace, a desk with two monitors, and a large abstract painting on the wall.

10. Hilton Garden Inn Madison Sun Prairie

Hilton Garden Inn Madison Sun Prairie
Sun Prairie
S$182
includes taxes & fees
1 Nov - 2 Nov
Hilton Garden Inn Madison Sun Prairie
View all properties

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
"."
Christine 1-night trip
Posted 1 hour ago
The Madison Concourse Hotel and Governor's Club
DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East

10/10 Excellent
"Rafi was great."
James 1-night trip
Posted 5 hours ago
DoubleTree by Hilton Madison East
Days Inn & Suites by Wyndham Madison

Days Inn & Suites by Wyndham Madison

10/10 Excellent
"."
Quartez 3-night trip
Posted 9 hours ago
Days Inn & Suites by Wyndham Madison
AmericInn by Wyndham Madison West

AmericInn by Wyndham Madison West

10/10 Excellent
"Staff was wonderful. Best breakfast I've had at a hotel. Free happy hour with nachos and popcorn. One of the best hotels I've stayed at. If I'm ever in the area again, I will definitely be back."
Sharilyn 6-night trip
Posted 11 hours ago
AmericInn by Wyndham Madison West
Best Western West Towne Suites

Best Western West Towne Suites

8/10 Good
"Aaa"
Bruce 2-night trip
Posted 1 day ago
Best Western West Towne Suites
Motel 6 Madison, WI - East

Motel 6 Madison, WI - East

10/10 Excellent
"Everything is perfect!"
Tingqing 4-night trip
Posted 2 days ago
Motel 6 Madison, WI - East

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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