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
23 Aug - 24 Aug
Tomorrow
24 Aug - 25 Aug
Next weekend
28 Aug - 30 Aug
In two weeks
4 Sep - 6 Sep

Our top choices for Windsor family-friendly hotels

Indoor pool
Exterior
Combined shower/tub, free toiletries, hair dryer, towels
Standard Room, 1 Queen Bed | Desk, iron/ironing board, cribs (free), rollaway beds (surcharge)

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.
AED 231
AED 244 total
includes taxes & fees
7 Sep - 8 Sep
Days Inn by Wyndham Madison NE/Windsor
Indoor pool
Lobby
In-room safe, desk, laptop workspace, iron/ironing board
Suite, 1 King Bed with Sofa bed, Non Smoking, Kitchenette (Whirlpool, Living Room) | In-room safe, desk, laptop workspace, iron/ironing board

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.
AED 309
AED 342 total
includes taxes & fees
30 Aug - 31 Aug
Comfort Inn & Suites Madison North
Indoor pool, sun loungers
Exterior
Lobby
Lobby

3. Best Western East Towne Suites

Best Western East Towne Suites
Madison
AED 312
AED 361 total
includes taxes & fees
27 Aug - 28 Aug
Best Western East Towne Suites
Indoor pool
Free daily buffet breakfast
Suite, 1 King Bed, Non Smoking | Laptop workspace, iron/ironing board, WiFi (free), alarm clocks
Fitness facility

4. Quality Inn & Suites Sun Prairie Madison East

Quality Inn & Suites Sun Prairie Madison East
Sun Prairie
  • Family-friendly paradise with indoor pool, fitness center, and free breakfast offers a fun, clean getaway for everyone.
AED 264
AED 298 total
includes taxes & fees
30 Aug - 31 Aug
Quality Inn & Suites Sun Prairie Madison East
Exterior
Lobby
Lounge
Breakfast and dinner served

5. Cambria Hotel Madison East

Cambria Hotel Madison East
Madison
AED 360
AED 416 total
includes taxes & fees
30 Aug - 31 Aug
Cambria Hotel Madison East
Combined shower/tub, free toiletries, hair dryer, towels
Lobby
Free daily continental breakfast
Whirlpool room, 1 King Bed, Non Smoking | Desk, blackout drapes, cribs (free), rollaway beds (surcharge)

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 center access just minutes away.
AED 235
AED 264 total
includes taxes & fees
20 Sep - 21 Sep
Super 8 by Wyndham Sun Prairie/Madison E
Reception
Exterior
Indoor pool, open 6:00 AM to 10:00 PM, sun loungers
Breakfast and dinner served

7. 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.
AED 358
AED 414 total
includes taxes & fees
6 Sep - 7 Sep
DoubleTree by Hilton Madison East
Lobby
In-room safe, rollaway beds (surcharge), WiFi (free), bed sheets
Standard Double Room, 2 Double Beds, Non Smoking | In-room safe, rollaway beds (surcharge), WiFi (free), bed sheets
Coffee and/or coffee maker

8. Econo Lodge Madison East

Econo Lodge Madison East
Greater Sandburg
AED 223
AED 258 total
includes taxes & fees
25 Aug - 26 Aug
Econo Lodge Madison East
Property amenity
Room, 2 Double Beds, Non Smoking | Desk, soundproofing, WiFi (free), bed sheets
Property amenity
Property amenity

9. AmericInn by Wyndham Madison WI

AmericInn by Wyndham Madison WI
Madison
AED 261
AED 302 total
includes taxes & fees
7 Sep - 8 Sep
AmericInn by Wyndham Madison WI
Desk, blackout drapes, bed sheets
Restaurant
Combined shower/tub, towels
Desk, blackout drapes, bed sheets

10. Motel 6 Madison, WI - East

Motel 6 Madison, WI - East
Madison
AED 187
AED 216 total
includes taxes & fees
6 Sep - 7 Sep
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

DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East

10/10 Excellent
"A well-kept DoubleTree. Friendly staff. Comfortable bed. Quiet room. Would stay here again."
Kenneth 1-night trip
Posted less than an hour ago
DoubleTree by Hilton Madison East
The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

8/10 Good
"Check in and out was very easy. Staff were friendly, didn’t have the food but the bar had good mixed drinks."
Aylssa 2-night trip
Posted 2 hours ago
The Madison Concourse Hotel and Governor's Club
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 6 days ago
Fairfield by Marriott Inn & Suites Madison South

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.