The Best Hotels with a Pool in Windsor, WI from ￥11,471 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. DoubleTree by Hilton Madison East : Features a snack bar/deli, an indoor pool, and complimentary wired internet access. Madison Marriott South : Hotel, 11-minute walk from Alliant Energy Center. Offers a snack bar/deli, a pool, and free self parking.

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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.

￥11,471 total

includes taxes & fees

Jun 7 - Jun 8

Holiday Inn Express Hotel & Suites Madison-Verona by IHG

Verona

Splash into endless fun at this pristine indoor pool with luxurious hot tub and sun loungers for post-swim relaxation.

￥18,889 total

includes taxes & fees

Jun 25 - Jun 26

Sleep Inn & Suites Oregon - Madison

Oregon

Take a refreshing dip in the indoor pool of this Madison hotel, where relaxation meets fitness with a hot tub on site.

￥13,307 total

includes taxes & fees

Jun 30 - Jul 1

AmericInn by Wyndham Madison West

Madison

Dive into a refreshing pool retreat with a hot tub and modern fitness center just steps away from your room.

￥11,931 total

includes taxes & fees

Jun 21 - Jun 22

Quality Inn & Suites Stoughton - Madison South

Stoughton

Serene indoor pool and hot tub retreat provides relaxation for weary travelers all day long.

￥13,415 total

includes taxes & fees

Jun 29 - Jun 30

Comfort Inn & Suites Madison East Interstate I-90

Madison

Relax at the indoor pool after exploring Madison, complete with a serene atmosphere and newly refreshed spaces throughout.

￥14,913 total

includes taxes & fees

Jun 22 - Jun 23

Baymont by Wyndham Madison West/Middleton WI West

Junction Ridge

Indoor pool and hot tub delight awaits at this Madison West retreat near the airport.

￥13,667 total

includes taxes & fees

Jun 8 - Jun 9

Hampton Inn Madison East Towne Mall Area

Greater Sandburg

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

￥18,021 total

includes taxes & fees

Jun 11 - Jun 12

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Choose what matters most at hotels with a pool in Windsor

Breakfast included

Hot tub

Top Windsor Hotel Reviews

The Edgewater

10/10 Excellent

"It’s all around amazing!!!"

Hampton Inn & Suites Madison-West

10/10 Excellent

"I can't say enough good things about our Stay at this Hampton Inn Hotel! Everything was Excellent. When We Arrived we were Upgraded to a King Suite by the Fantastic Front Desk Attendant, I didn't catch her Name,I'm sorry for that. She was very Corteous and even offered us complimentary water bottles. We stayed at this Hotel in 2025 and we returned because we really liked the Hotel and the Staff. The Hotel is Very clean,Breakfast was Phenomenal. Our Room was Clean and spacious, we had a good night sleep on the Comfy Bed.Great View from the 5th floor. We Highly recommend this Hampton Inn, there's plenty to do around the Madison Area. We will definitely be back to this Hotel on our next weekend getaway. Thank you for Everything!⭐️⭐️⭐️⭐️⭐️"

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. DoubleTree by Hilton Madison East: Features a snack bar/deli, an indoor pool, and complimentary wired internet access. Madison Marriott South: Hotel, 11-minute walk from Alliant Energy Center. Offers a snack bar/deli, a pool, and free self parking.

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, 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 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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