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
26 Aug - 27 Aug
Tomorrow
27 Aug - 28 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

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$84
includes taxes & fees
7 Sept - 8 Sept
Days Inn by Wyndham Madison NE/Windsor
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 lobby with a staircase, blue sofa, red chairs, a fireplace, and a reception desk.
A hotel room with a blue sofa, a brown ottoman, a white bathtub, and a large mirror.

2. 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$120
includes taxes & fees
20 Sept - 21 Sept
Comfort Inn & Suites Madison North
An indoor swimming pool with two separate sections, one with clear water and the other with a whirlpool feature. There are lounge chairs and umbrellas around the pool area, and large windows providing views of the outside.
A spacious lobby with a high ceiling, a large chandelier, and a seating area with patterned chairs and a sofa.
A sunlit patio area with cushioned seating, a table, and a large umbrella.
A modern building with a covered entrance, large windows, and a visible address sign.

3. Best Western East Towne Suites

Best Western East Towne Suites
Madison
S$125
includes taxes & fees
2 Sept - 3 Sept
Best Western East Towne Suites
An indoor swimming pool with clear blue water, surrounded by wooden walls and large windows.
A dining area with wooden tables and chairs, a kitchen in the background, and a clock on the wall.
A gym with cardio machines, weight machines, and a mirrored wall.
A hotel room with a large bed, a desk with a computer, a sofa, a TV, a bathroom with a bathtub, and a large mirror.

4. Quality Inn & Suites Sun Prairie Madison East

Quality Inn & Suites Sun Prairie Madison East
Sun Prairie
  • Family-friendly paradise with indoor pool, fitness centre, and free breakfast offers a fun, clean getaway for everyone.
S$103
includes taxes & fees
6 Sept - 7 Sept
Quality Inn & Suites Sun Prairie Madison East
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 modern bar area with a long counter, bar stools, and a television mounted above the bar.
An indoor swimming pool with clear depth markings, safety signs, and a lifeguard on duty.

5. Cambria Hotel Madison East

Cambria Hotel Madison East
Madison
S$152
includes taxes & fees
30 Aug - 31 Aug
Cambria Hotel Madison East
A bathroom with a shower, a sink, a mirror, and a towel rack.
A compact living space with a grey sofa, a red sofa, a wooden dining table with chairs, a kitchen area with a microwave, and a framed picture on the wall.
A modern bathroom with a large freestanding bathtub, a mirror, and a towel rack.
A reception area with a grey sofa, two side tables with lamps, a blue chair, and a reception desk with a blue wall.

6. Super 8 by Wyndham Sun Prairie/Madison E

Super 8 by Wyndham Sun Prairie/Madison E
Sun Prairie
  • Family-friendly oasis in Sun Prairie offers a comfortable home base with convenient aquatic centre access just minutes away.
S$91
includes taxes & fees
20 Sept - 21 Sept
Super 8 by Wyndham Sun Prairie/Madison E
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.

7. 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$143
includes taxes & fees
6 Sept - 7 Sept
DoubleTree by Hilton Madison East
A hotel reception area with a reception desk, a fireplace, and a seating area.
A bathroom with a shower, a bathtub, and a toilet. There are towels hanging on a rack.
A hotel room with a large bed, a sofa, a small table, a nightstand with a lamp, and a window with curtains.
A modern kitchen with a built-in coffee station, a fireplace, and a flat-screen TV mounted on the wall.

8. Econo Lodge Madison East

Econo Lodge Madison East
Greater Sandburg
S$89
includes taxes & fees
2 Sept - 3 Sept
Econo Lodge Madison East
A kitchen area with a stone backsplash, a coffee station with dispensers, and a buffet setup with bowls and cups.
A hotel room with two beds, a desk, a chair, and a window with a view of buildings.
A modern interior with a kitchen area, a seating area with a table and chairs, and a staircase leading to an outdoor area.
A hotel room with a leather chair, a bedside table with a coffee maker, and a TV mounted on the wall.

9. AmericInn by Wyndham Madison WI

AmericInn by Wyndham Madison WI
Madison
S$103
includes taxes & fees
7 Sept - 8 Sept
AmericInn by Wyndham Madison WI
A compact room with a brick wall, a flat-screen TV, a microwave, and a refrigerator.
A kitchen with wooden cabinets, a granite countertop, and two potted plants.
A modern room with a flat-screen TV, a desk, a chair, a sofa, and a table.
A bathroom with a granite sink, a mirror, a toilet, and a glass shower enclosure.

10. Motel 6 Madison, WI - East

Motel 6 Madison, WI - East
Madison
S$75
includes taxes & fees
9 Sept - 10 Sept
Motel 6 Madison, WI - East
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
"Wonderful hotel. Check in was quick and easy. The parking garage was wonderful and so convenient. The floors are beautiful and my room was so spacious. I enjoyed the pool, which was a fantastic temperature. I really loved the extra security of needing to scan a room key to get to any floor that has rooms, especially as a solo female traveler. The vending machines were so convenient as was the Starbucks in the lobby. Highly recommend!"
Jennifer 1-night trip
Posted 2 hours ago
The Madison Concourse Hotel and Governor's Club
Days Inn by Wyndham Madison NE/Windsor

Days Inn by Wyndham Madison NE/Windsor

8/10 Good
"The check-in process was efficient. This hotel completely served my needs, which just entailed a clean room & shower for one overnight as I passed through town. The continental breakfast was bare bones though. I would stay there again but not for an extended time."
Bonnie 1-night trip
Posted 9 hours ago
Days Inn by Wyndham Madison NE/Windsor
Cambria Hotel Madison East

Cambria Hotel Madison East

10/10 Excellent
"Easy check in and check out. Friendly and helpful staff. I was surprised that they did not have a complimentary breakfast. Room was quite nice, roomy and comfortable."
BARRY 1-night trip
Posted 1 day ago
Cambria Hotel Madison East
Best Western Plus InnTowner Madison

Best Western Plus InnTowner Madison

10/10 Excellent
"Room was clean, quiet, and comfortable."
Susan 1-night trip
Posted 1 day ago
Best Western Plus InnTowner Madison
La Quinta Inn & Suites by Wyndham Madison American Center

La Quinta Inn & Suites by Wyndham Madison American Center

8/10 Good
"Front desk staff were awesomeโ€ฆhelping us with things we had forgotten to bring. They also accommodated our friends who had come to visit and play board games in the dining area late into the night. The pool was fun and the room was cleaned daily. Our only concern was that my wife had some difficulty getting into and out of the tub, as it had no non skid surface in the tub."
Arthur 3-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Madison American Center
Comfort Suites Madison West - Middleton

Comfort Suites Madison West - Middleton

8/10 Good
"Was good for the price but honestly the beds weren't comfortable and snacks are way overpriced"
Matthew 1-night trip
Posted 2 days ago
Comfort Suites Madison West - Middleton
DoubleTree by Hilton Madison Downtown

DoubleTree by Hilton Madison Downtown

10/10 Excellent
"Friendly staff"
Richard 2-night trip
Posted 2 days ago
DoubleTree by Hilton Madison Downtown
Fairfield by Marriott Inn & Suites Madison South

Fairfield by Marriott Inn & Suites Madison South

10/10 Excellent
"Nice stay, would come here again!"
Merritt 5-night trip
Posted 8 days ago
Fairfield by Marriott Inn & Suites Madison South

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 20ยฐC, while the coldest months are January and February, with an average of -4ยฐC. 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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