Hotels with Swimming Pool in Greendale, Milwaukee

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Check availability on Greendale Hotels with Swimming Pool

Tonight
Dec 29 - Dec 30
Tomorrow
Dec 30 - Dec 31
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Greendale hotels with a pool

Indoor pool
Holiday Inn Express & Suites New Berlin by IHG

Holiday Inn Express & Suites New Berlin by IHG

Holiday Inn Express & Suites New Berlin by IHG
2.5 star property
New Berlin
9.2 out of 10, Wonderful, (920)
"The room was very clean and the breakfast was wonderful"
United States
Kari
The price is P5,346
P6,041 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Holiday Inn Express & Suites New Berlin by IHG
Bar (on property)
Marriott Milwaukee West

Marriott Milwaukee West

Marriott Milwaukee West
3.5 star property
Waukesha
9.2 out of 10, Wonderful, (1001)
"A very clean and accommodating hotel. We will stay here again!"
United States
David
The price is P6,063
P6,851 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Marriott Milwaukee West
Indoor pool
Drury Plaza Hotel Milwaukee Downtown

Drury Plaza Hotel Milwaukee Downtown

Drury Plaza Hotel Milwaukee Downtown
3.0 star property
Downtown Milwaukee
9.6 out of 10, Exceptional, (2004)
"From check in to check out staff and facilities were great! "
United States
Leslie
The price is P5,874
P6,926 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Drury Plaza Hotel Milwaukee Downtown
Indoor pool
Country Inn & Suites by Radisson, Mt. Pleasant-Racine West, WI

Country Inn & Suites by Radisson, Mt. Pleasant-Racine West, WI

Country Inn & Suites by Radisson, Mt. Pleasant-Racine West, WI
2.5 star property
Mount Pleasant
8.8 out of 10, Excellent, (1001)
"My stay here is always AMAZING!!!"
United States
Lauren
The price is P4,661
P5,584 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Country Inn & Suites by Radisson, Mt. Pleasant-Racine West, WI
Indoor pool
Hampton Inn & Suites Milwaukee/Franklin

Hampton Inn & Suites Milwaukee/Franklin

Hampton Inn & Suites Milwaukee/Franklin
2.5 star property
Franklin
9.4 out of 10, Exceptional, (731)
"nice hotel for the price "
United States
Courtney
The price is P5,251
P6,138 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Hampton Inn & Suites Milwaukee/Franklin
Indoor pool
Wildwood Lodge

Wildwood Lodge

Wildwood Lodge
2.5 star property
Pewaukee
8.6 out of 10, Excellent, (1004)
"Front desk staff was so friendly and professional, location convenient and the area dining never disappoints. "
United States
Rodney
The price is P4,449
P5,028 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Wildwood Lodge
Free daily continental breakfast
Baymont by Wyndham Waterford/Burlington WI

Baymont by Wyndham Waterford/Burlington WI

Baymont by Wyndham Waterford/Burlington WI
2.5 star property
Waterford
7.4 out of 10, Good, (437)
"The room was spacious with a comfortable bed. "
United States
Jill
The price is P4,494
P5,101 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Baymont by Wyndham Waterford/Burlington WI
Indoor pool
Aloft Milwaukee Downtown

Aloft Milwaukee Downtown

Aloft Milwaukee Downtown
3.0 star property
Westown
8.6 out of 10, Excellent, (1006)
"Great stay"
United States
KENT
The price is P5,635
P6,644 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Aloft Milwaukee Downtown
Indoor pool, open 6:00 AM to 10 PM, sun loungers
The Pfister Hotel

The Pfister Hotel

The Pfister Hotel
4.5 star property
Downtown Milwaukee
9.6 out of 10, Exceptional, (1848)
"Wonderful stay"
United States
jeffrey
The price is P7,602
P8,963 total
includes taxes & fees
Jan 19 - Jan 20, 2026
The Pfister Hotel
Indoor pool
Sleep Inn & Suites Milwaukee/Franklin

Sleep Inn & Suites Milwaukee/Franklin

Sleep Inn & Suites Milwaukee/Franklin
2.5 star property
Franklin
9.2 out of 10, Wonderful, (284)
"Front desk staff was very courteous and accommodating. Breakfast was great with many food selections. "
United States
Joseph
The price is P4,699
P5,493 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Sleep Inn & Suites Milwaukee/Franklin
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Greendale Hotel Reviews

The Iron Horse Hotel

The Iron Horse Hotel

10/10 Excellent
"Clean quiet cool hotel"
Henry 1-night trip
Posted 13 hours ago
The Iron Horse Hotel

Frequently asked questions

What are some hotels with pools in Greendale?
The Pfister Hotel: Hotel, 14-minute walk from Lake Michigan. Features 2 restaurants, an indoor pool, and a full-service spa. Saint Kate - The Arts Hotel: Offers a snack bar/deli, an indoor pool, and complimentary wireless internet access. The Iron Horse Hotel: Hotel, 9-minute walk from Baird Center. Features buffet, a pool, and complimentary wireless internet access. Ambassador Hotel Milwaukee, Trademark Collection by Wyndham: Provides buffet, an indoor pool, and complimentary wired internet access. Crowne Plaza Milwaukee Airport by IHG: Offers free self parking, an indoor pool, and complimentary wireless internet access.
What is there to see and do in Greendale?
Take a walk along the waterfront at Bradford Beach and Pebble Beach. Discover sights such as Rock Snow Park during your stay.
When is the best time to book a hotel with a pool in Greendale?
Taking into account the local weather in Greendale can help you maximize your time at the pool during your trip. 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 28°F. The snowiest months in Greendale are January, March, October, and February, with each month seeing an average of 8 inches of snowfall.

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