Book the Best Hotels with POOL in Southwest Wisconsin in 2026

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Our top choices for Southwest Wisconsin hotels with a pool

A wooden cabin with a swimming pool, large windows, and a patio area.

1. AmericInn by Wyndham Boscobel

Boscobel

Splash into mountain adventures with an indoor pool and steamy hot tub to refresh after outdoor thrills.

CA $129 total

includes taxes & fees

Nov 14 - Nov 15

An indoor swimming pool with wooden walls and a stone floor, surrounded by chairs and a small hot tub.

2. Best Western Park Oasis Inn

Mauston

Dive into refreshing relaxation with indoor and seasonal outdoor pools, plus a hot tub retreat.

CA $137 total

includes taxes & fees

Nov 29 - Nov 30

A water feature with wooden barrels and a pool area.

3. Cranberry Country Lodge

Tomah

Splash into family fun with an indoor pool oasis and relaxing hot tub retreat for all ages.

CA $131 total

includes taxes & fees

Dec 7 - Dec 8

An indoor swimming pool with multiple lanes, lounge chairs, and a bar area.

4. Cedarberry Inn

Sauk City

Dive into refreshing pool adventures with a relaxing hot tub waiting for your tired muscles after exploring riverside trails.

CA $176 total

includes taxes & fees

Nov 16 - Nov 17

An indoor swimming pool with a bear statue, a tree sculpture, and a bear statue holding a fish.

5. Comfort Inn & Suites Black River Falls I-94

Black River Falls

Splash into comfort at this hotel's indoor pool haven, perfect for family play and relaxation time after exploring.

CA $141 total

includes taxes & fees

Dec 3 - Dec 4

An indoor swimming pool with a basketball hoop, multiple windows, and seating areas.

6. The Lodge at Mauston

Mauston

Splash into serenity at this hotel's pristine indoor pool sanctuary with loungers for post-adventure unwinding.

CA $228 total

includes taxes & fees

Nov 16 - Nov 17

A bear in an indoor water park with slides and a tree-like structure.

7. Country Inn & Suites by Radisson, Prairie du Chien

Prairie Du Chien

Splash into family fun with this indoor pool wonderland featuring special kids' areas and a relaxing hot tub.

CA $115 total

includes taxes & fees

Dec 13 - Dec 14

An indoor swimming pool with clear blue water, surrounded by wooden walls and a tiled floor.

8. Sleep Inn & Suites Wisconsin Dells - Lake Delton

Lake Delton

Take a refreshing plunge in this newly renovated hotel with a sparkling indoor pool.

CA $88 total

includes taxes & fees

Dec 14 - Dec 15

An indoor water park with a slide, a rock waterfall, and a paddle boat area.

9. Hilton Vacation Club Christmas Mountain Village

Wisconsin Dells

CA $172 total

includes taxes & fees

Nov 16 - Nov 17

An indoor swimming pool with clear water, a lifeguard chair, and a sign indicating spa capacity.

10. Staybridge Suites Wisconsin Dells - Lake Delton by IHG

Wisconsin Dells

Dive into splash-tastic family fun with an indoor pool and hot tub that makes every season swim season.

CA $175 total

includes taxes & fees

Nov 23 - Nov 24

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Choose what matters most at hotels with a pool in Southwest Wisconsin

Breakfast included

4 stars

Top Southwest Wisconsin Hotel Reviews

An indoor water park with a central pool, a slide, and a staircase leading to a platform.

The Wisconsin Hotel & Conference Center

Wisconsin Dells

10/10 Excellent

Allan

An indoor swimming pool with a lifeguard sign, chairs, and a no diving sign.

Holiday Inn Express & Suites Madison Central by IHG

Madison

10/10 Excellent

Marwa

A swimming pool with four lounge chairs and large windows with a view of trees.

Holiday Inn Express & Suites Sauk City by IHG

Sauk City

10/10 Excellent

Tara

An indoor swimming pool with clear safety markings, a lifeguard chair, and a view of the outside through large windows.

Holiday Inn Express and Suites-Platteville by IHG

Platteville

8/10 Good

This was a quick trip to watch my son play baseball. The staff was really friendly and helpful. I asked the front desk for extra blankets and he was happy to go get them for me. He may have returned with just sheets, but he tried. The bed was comfortable, the bathroom was clean, the TV worked, the wifi worked, I didn't have a noise issue and the hotel is clearly up to date. There are a bunch of, restaurants, bars, and stores within easy walking distance, which made it really nice that I...

Anonymous traveller

An indoor swimming pool with clear blue water, surrounded by lounge chairs and a view of the outdoors.

Holiday Inn Express & Suites Madison West - Middleton by IHG

Middleton

10/10 Excellent

Daragh

An indoor swimming pool with clear signage, a lifeguard stand, and a seating area with chairs.

Comfort Suites Cottage Grove – Madison

Village of Cottage Grove

10/10 Excellent

Linda

An indoor swimming pool with a red and white color scheme, seating areas, and large windows.

Hampton Inn & Suites Madison / Downtown

Downtown Madison

10/10 Excellent

Rosemary

An indoor swimming pool with clear views through large windows, surrounded by seating areas and a modern interior design.

Home2 Suites by Hilton Madison Central Alliant Energy Center

Madison

10/10 Excellent

Clement

An indoor swimming pool with clear water, a diving board, and a view of the outdoors through large windows.

Sleep Inn & Suites Lancaster-Platteville

Lancaster

10/10 Excellent

Andre

An indoor swimming pool with clear glass walls, red chairs, and a table with chairs.

Hampton Inn Madison East Towne Mall Area

Greater Sandburg

10/10 Excellent

We stayed for 1 night as we were passing through on our way home from our road trip to see family. Our experience at this hotel was exceptional! From check in, to our room which had a very comfortable bed, the pool and hot tub, and the breakfast that included a variety of hot and cold items. We will definitely stay here again if we find ourselves in the area! We highly recommend this hotel to others!

Brenda

Find Hotels with a Pool in Southwest Wisconsin, WI from CA $78

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Southwest Wisconsin hotels with a pool

1. AmericInn by Wyndham Boscobel

2. Best Western Park Oasis Inn

3. Cranberry Country Lodge

4. Cedarberry Inn

5. Comfort Inn & Suites Black River Falls I-94

6. The Lodge at Mauston

7. Country Inn & Suites by Radisson, Prairie du Chien

8. Sleep Inn & Suites Wisconsin Dells - Lake Delton

9. Hilton Vacation Club Christmas Mountain Village

10. Staybridge Suites Wisconsin Dells - Lake Delton by IHG

Choose what matters most at hotels with a pool in Southwest Wisconsin

Top Southwest Wisconsin Hotel Reviews

The Wisconsin Hotel & Conference Center

10/10 Excellent

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