TOP Hotels with Pool in Windsor, WI for 2026

A park with a statue of a figure on horseback, surrounded by leafless trees and a clear sky.

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Our top choices for Windsor hotels with a pool

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 hotel room with a large bed, a desk with a computer, a chair, a window with curtains, and a painting on the wall.

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

Year-round swimming awaits at this Madison hotel's indoor pool with soothing hot tub oasis.

1.722.076 ₫

1.816.790 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

A snack and beverage vending area with multiple shelves stocked with various snacks and a refrigerated section with bottled drinks.

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

De Forest

Experience the indoor pool oasis with heated waters and comfortable sun loungers at this suburban retreat with hot tub access.

2.363.634 ₫

2.611.814 ₫ total

includes taxes & fees

1 Nov - 2 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 lobby with a staircase, blue sofa, red chairs, a fireplace, and a reception desk.

A hotel room with a bed, a blue sofa, two small tables, a lamp, and two framed pictures on the wall.

3. Comfort Inn & Suites Madison North

De Forest

Splash into relaxation at this family-friendly hotel featuring indoor pools and a bubbling hot tub.

2.177.660 ₫

2.406.314 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

A lobby with a fireplace, two armchairs, and two small tables.

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

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

Madison

Serene suburban hotel boasts a relaxing indoor pool oasis and soothing hot tub with premium amenities just minutes from dining.

2.080.517 ₫

2.403.114 ₫ total

includes taxes & fees

4 Oct - 5 Oct

An indoor swimming pool with clear markings for non-diving and diving areas, surrounded by lounge chairs and tables.

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

Greater Sandburg

Dive into a freshly renovated indoor pool sanctuary with plush sun loungers at this Madison retreat.

2.619.738 ₫

3.025.797 ₫ total

includes taxes & fees

4 Oct - 5 Oct

An indoor swimming pool with clear depth markings, safety signs, and a lifeguard on duty.

A multi-story hotel with a prominent 'CAMBRIA' sign, featuring a brick facade, large windows, and a covered entrance area.

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.

6. Cambria Hotel Madison East

Madison

Splash into ultimate relaxation at this indoor pool hotel where aquatic fun meets fitness possibilities.

2.185.712 ₫

2.524.498 ₫ total

includes taxes & fees

1 Nov - 2 Nov

An indoor swimming pool with multiple lounge chairs and a sign indicating no lifeguard on duty.

A hotel lobby with multiple seating areas, a bar, and a fireplace.

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.

7. Fairfield Inn & Suites by Marriott Madison East

Madison

Splash into art deco elegance at this Madison East retreat with indoor pool and bubbling hot tub.

2.548.049 ₫

2.942.996 ₫ total

includes taxes & fees

29 Oct - 30 Oct

An indoor swimming pool with a stone wall, a seating area with chairs, and a sign indicating no lifeguard on duty.

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.

8. Holiday Inn Madison at The American Center by IHG

Madison

Experience a revitalising dip at this hotel's indoor pool with hot tub, steps away from a 24-hour fitness centre.

2.259.738 ₫

2.609.998 ₫ total

includes taxes & fees

1 Nov - 2 Nov

View all properties

Choose what matters most at hotels with a pool in Windsor

Breakfast included

Hot tub

4 stars

5 stars

Spa

Top Windsor Hotel Reviews

Best Western Plus InnTowner Madison

10/10 Excellent

"Great breakfast"

Super 8 by Wyndham Madison South

8/10 Good

"X"

The Madison Concourse Hotel and Governor's Club

10/10 Excellent

"Outstanding location and property. My wife and I will be returning for certain!"

Comfort Suites Madison West - Middleton

8/10 Good

"The breakfast was not ready on time. All utensils in the breakfast area were covered in dust. The coffee was also poorly made"

DoubleTree by Hilton Madison East

10/10 Excellent

"Great spot for quick stay-overs! Reasonable and convenient to our needs!"

La Quinta Inn & Suites by Wyndham Madison American Center

8/10 Good

"Good for the price. Some mystery stains on the couch. Pet friendly. Great staff."

Baymont by Wyndham Madison West/Middleton WI West

10/10 Excellent

"The property was clean and the building was cleaned regularly."

AmericInn by Wyndham Madison West

10/10 Excellent

"We make an annual trip to Madison, and we always stay in the AmericInn. It is affordable, dependably clean, and has a tasty breakfast with good variety."

Hampton Inn & Suites Madison-West

10/10 Excellent

"As always terrific staff and great rooms."

Frequently asked questions

What is there to see and do in Windsor?

Make a point to visit attractions such as Mousehouse Cheesehaus. During your stay, visit sights such as East Towne Mall, Madison Area Technical College and Olbrich Botanical Gardens. You'll also discover lots of options for restaurants in Windsor.

When is the best time to book a hotel with a pool in Windsor?

Taking the local weather in Windsor into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. 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.

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Check availability on Windsor Hotels with Pool

Our top choices for Windsor hotels with a pool

1. Days Inn by Wyndham Madison NE/Windsor