The Best Hotels with a Pool in Windsor, WI from ￥11,846 in 2026

Q: What are some accommodations with pools in Windsor?

Days Inn by Wyndham Madison NE/Windsor : Features a sauna, an indoor pool, and daily. The Madison Concourse Hotel and Governor's Club : Hotel, 1-minute walk from Capitol Square. Offers a health club, an indoor pool, and a sauna. Baymont by Wyndham Madison West/Middleton WI West : Provides continental, an indoor pool, and free self parking. Best Western Plus InnTowner Madison : Hotel, 3-minute walk from University of Wisconsin-Madison. Features a snack bar/deli, a pool, and buffet. AmericInn by Wyndham Madison West : Offers a snack bar/deli, an indoor pool, and buffet.

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

Days Inn by Wyndham Madison NE/Windsor

Windsor

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

￥11,846 total

includes taxes & fees

Aug 9 - Aug 10

Indoor pool, open 6:00 AM to 11:00 PM, sun loungers

Holiday Inn Express & Suites Madison by IHG

Madison

Splash into the Madison scene in an indoor pool paradise with loungers for post-adventure refreshment.

￥18,823 total

includes taxes & fees

Aug 9 - Aug 10

Holiday Inn Express & Suites Madison West - Middleton by IHG

Middleton

Splash into comfort at this Middleton retreat with an indoor pool and poolside loungers.

￥12,959 total

includes taxes & fees

Aug 23 - Aug 24

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.

￥18,480 total

includes taxes & fees

Aug 9 - Aug 10

Holiday Inn Madison at The American Center by IHG

Madison

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

￥13,889 total

includes taxes & fees

Aug 23 - Aug 24

Indoor pool, open 7 AM to 11 PM, pool umbrellas, sun loungers

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.

￥16,761 total

includes taxes & fees

Aug 2 - Aug 3

Hampton Inn Madison East Towne Mall Area

Greater Sandburg

Dive into a refreshing indoor pool retreat with alpine adventure options right outside your door.

￥20,097 total

includes taxes & fees

Aug 3 - Aug 4

Indoor pool, open 6:00 AM to 10:00 PM, sun loungers

DoubleTree by Hilton Madison East

Greater Sandburg

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

￥20,080 total

includes taxes & fees

Aug 6 - Aug 7

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Choose what matters most at hotels with a pool in Windsor

Breakfast included

Hot tub

Top Windsor Hotel Reviews

AmericInn by Wyndham Madison West

10/10 Excellent

"Perfect place to stay the night of a concert at Camp Randall!"

La Quinta Inn & Suites by Wyndham Madison American Center

8/10 Good

"The service was great, the breakfast was good but same each day, the exercise room and pool were average, (pool had crazy loud young boys playing soccer…. As boys are supposed to do… so couldn’t swim when I wanted to. All and all well worth the price of around $100/day. Oh, and VERY quiet location away from freeway."

Frequently asked questions

What are some accommodations with pools in Windsor?

Days Inn by Wyndham Madison NE/Windsor: Features a sauna, an indoor pool, and daily. The Madison Concourse Hotel and Governor's Club: Hotel, 1-minute walk from Capitol Square. Offers a health club, an indoor pool, and a sauna. Baymont by Wyndham Madison West/Middleton WI West: Provides continental, an indoor pool, and free self parking. Best Western Plus InnTowner Madison: Hotel, 3-minute walk from University of Wisconsin-Madison. Features a snack bar/deli, a pool, and buffet. AmericInn by Wyndham Madison West: Offers a snack bar/deli, an indoor pool, and buffet.

What is there to see and do in Windsor?

Make a point to visit attractions like Mousehouse Cheesehaus. During your stay, check out sights such as East Towne Mall, Olbrich Botanical Gardens, and Barrymore Theatre. 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 into account the local weather in Windsor is an important factor for planning your visit, especially if you plan to spend your trip poolside. 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.

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