Title: Book the Best Hotels with POOL in Pewaukee in 2026 | Expedia.ca [Pewaukee Travel Guide](https://expedia.ca/Pewaukee.dx145269)[Hotels in Pewaukee](https://expedia.ca/Pewaukee-Hotels.d145269.Travel-Guide-Hotels)[Vacation Rentals in Pewaukee](https://expedia.ca/Pewaukee-Vacation-Rentals.d145269.Travel-Guide-VacationRentals)[Pewaukee Car Rentals](https://expedia.ca/Car-Rentals-In-Pewaukee.d145269.Car-Rental-Guide)[Pewaukee Vacation Packages](https://expedia.ca/Pewaukee.d145269.Destination-Travel-Guides) ![Pewaukee Lake Wisconsin Sunset After Summer Storm](https://images.trvl-media.com/place/145269/aee1c4a9-c25b-4b5e-bc0d-b3dfebe76004.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/145269/aee1c4a9-c25b-4b5e-bc0d-b3dfebe76004.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Pewaukee Hotels with a Pool Tonight [Feb 28 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=145269&startDate=2026-02-28&endDate=2026-03-01&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 1 - Mar 2](https://www.expedia.ca/Hotel-Search?regionId=145269&startDate=2026-03-01&endDate=2026-03-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=145269&startDate=2026-03-06&endDate=2026-03-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=145269&startDate=2026-03-13&endDate=2026-03-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Pewaukee hotels with a pool ![Indoor pool](https://images.trvl-media.com/lodging/1000000/70000/62400/62392/df5b1987.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Whirlpool Suite Accessible](https://images.trvl-media.com/lodging/1000000/70000/62400/62392/a69d61f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/70000/62400/62392/d0d1c4ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/70000/62400/62392/eb6ccca2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wildwood Lodge [](https://www.expedia.ca/Milwaukee-Hotels-Wildwood-Lodge.h62392.Hotel-Information) Pewaukee 8.6/10 Excellent (1,002 reviews) - Make a splash at this woodland retreat with a pristine indoor pool and rejuvenating hot tub for year-round aquatic enjoyment. [](https://www.expedia.ca/Milwaukee-Hotels-Wildwood-Lodge.h62392.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/580000/579400/579313/a2dde454.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/580000/579400/579313/a6bf6ae5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/580000/579400/579313/f8453d59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/580000/579400/579313/7138e0b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Pewaukee - Milwaukee West by IHG [](https://www.expedia.ca/Milwaukee-Hotels-Holiday-Inn-Pewaukee-Milwaukee-West.h579313.Hotel-Information) Pewaukee 9.0/10 Wonderful (473 reviews) - Splash into pure relaxation at the indoor pool and hot tub, where leisure is available all year long. CA $150 CA $170 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Milwaukee-Hotels-Holiday-Inn-Pewaukee-Milwaukee-West.h579313.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/670000/663900/663812/a045f8dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/670000/663900/663812/6b221df7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, rollaway beds](https://images.trvl-media.com/lodging/1000000/670000/663900/663812/25dce840.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/670000/663900/663812/b4c5d363.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Waukesha Grand [](https://www.expedia.ca/Milwaukee-Hotels-Best-Western-Waukesha-Grand.h663812.Hotel-Information) Pewaukee 7.8/10 Good (1,002 reviews) - Luxurious indoor pool sanctuary with year-round swimming and a rejuvenating hot tub for post-adventure relaxation. CA $97 CA $110 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Milwaukee-Hotels-Best-Western-Waukesha-Grand.h663812.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/894100/894006/8211d654.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite - No Water Park Included | Minibar](https://images.trvl-media.com/lodging/1000000/900000/894100/894006/59150dc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Food and drink](https://images.trvl-media.com/lodging/1000000/900000/894100/894006/a3a0afad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/900000/894100/894006/ad50967c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ingleside Hotel [](https://www.expedia.ca/Milwaukee-Hotels-The-Ingleside-Hotel.h894006.Hotel-Information) Pewaukee 8.6/10 Excellent (773 reviews) - Splash into vacation bliss at this family-friendly hotel featuring a whimsical water park. CA $131 CA $149 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Milwaukee-Hotels-The-Ingleside-Hotel.h894006.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/124000000/123950000/123948300/123948214/492d0b55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/124000000/123950000/123948300/123948214/a5255d5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/124000000/123950000/123948300/123948214/2710bc0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/124000000/123950000/123948300/123948214/8e854e63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites By Radisson, Brown Deer - Milwaukee North [](https://www.expedia.ca/Milwaukee-Hotels-Country-Inn-Suites-By-Radisson.h123948214.Hotel-Information) Brown Deer 9.4/10 Exceptional (32 reviews) CA $109 CA $133 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Milwaukee-Hotels-Country-Inn-Suites-By-Radisson.h123948214.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/70000/67600/67577/a98f50d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Double Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/70000/67600/67577/a747cd89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/70000/67600/67577/2152864c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free continental breakfast](https://images.trvl-media.com/lodging/1000000/70000/67600/67577/ccb7b545.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Milwaukee Delafield [](https://www.expedia.ca/Milwaukee-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Milwaukee-Delafield.h67577.Hotel-Information) Delafield 8.6/10 Excellent (1,001 reviews) - Plunge into aquatic bliss with a scenic indoor pool and soothing hot tub, perfect for relaxation after exploring nearby trails. CA $107 CA $121 total includes taxes & fees Mar 16 - Mar 17 [](https://www.expedia.ca/Milwaukee-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Milwaukee-Delafield.h67577.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/970000/970000/969958/cea40602.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/970000/970000/969958/32acf947.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/1000000/970000/970000/969958/2d6f031f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/970000/970000/969958/9dc94673.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### AmericInn by Wyndham Hartford WI [](https://www.expedia.ca/Hartford-Hotels-AmericInn-By-Wyndham-Hartford-WI.h969958.Hotel-Information) Hartford 8.2/10 Very good (541 reviews) - Splash into comfort at this hotel's weather-proof indoor pool with après-ski relaxation. CA $111 CA $125 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Hartford-Hotels-AmericInn-By-Wyndham-Hartford-WI.h969958.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/670000/661000/660970/e6ac4598.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/670000/661000/660970/ea9f87c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/670000/661000/660970/fb4c82e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/670000/661000/660970/e910adbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Jackson - West Bend [](https://www.expedia.ca/Jackson-Hotels-Comfort-Inn-Suites-Jackson-West-Bend.h660970.Hotel-Information) Jackson 9.0/10 Wonderful (580 reviews) - Dive into aquatic relaxation at this modern hotel where guests enjoy a sparkling indoor pool and soothing hot tub retreat. CA $109 CA $120 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Jackson-Hotels-Comfort-Inn-Suites-Jackson-West-Bend.h660970.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/102000000/101370000/101362600/101362597/7c5f39ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101370000/101362600/101362597/58cdc3ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/102000000/101370000/101362600/101362597/93df971c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/102000000/101370000/101362600/101362597/85683d93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Inn & Suites Milwaukee/Franklin [](https://www.expedia.ca/Milwaukee-Hotels-Sleep-Inn-Suites.h101362597.Hotel-Information) Franklin 9.2/10 Wonderful (312 reviews) - Year-round aquatic bliss awaits at this Milwaukee hotel's pristine indoor pool. CA $121 CA $141 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Milwaukee-Hotels-Sleep-Inn-Suites.h101362597.Hotel-Information) ![Indoor pool, open 6 AM to 11:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/70000/60800/60775/3078d14c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/60800/60775/eb92b896.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/70000/60800/60775/fbc07bdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/60800/60775/f17c0f1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Delafield by IHG [](https://www.expedia.ca/Milwaukee-Hotels-Holiday-Inn-Express-Suites-Delafield.h60775.Hotel-Information) Delafield 9.4/10 Exceptional (617 reviews) - Splash into morning swims and evening relaxation at this recently renovated hotel with an indoor pool and hot tub. CA $140 CA $159 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Milwaukee-Hotels-Holiday-Inn-Express-Suites-Delafield.h60775.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-03-14&endDate=2026-03-15®ionId=145269&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Pewaukee Breakfast included Hot tub 4 stars Water park 5 stars ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AFFINITY_SPRING_PROMO_145269) ## Top Pewaukee Hotel Reviews ![The Iron Horse Hotel](https://images.trvl-media.com/lodging/3000000/2100000/2097200/2097106/2030b501_y.jpg) ### The Iron Horse Hotel 10/10 Excellent "good" [](https://expedia.ca/Milwaukee-Hotels-The-Iron-Horse-Hotel.h2097106.Hotel-Information) ![Saint Kate - The Arts Hotel](https://images.trvl-media.com/lodging/1000000/30000/23300/23253/63d91083_y.jpg) ### Saint Kate - The Arts Hotel 10/10 Excellent "A really special place. Staff are friendly, spaces are well thought out and the art is fantastic." [](https://expedia.ca/Milwaukee-Hotels-Saint-Kate-The-Arts-Hotel.h23253.Hotel-Information) ![The Pfister Hotel](https://images.trvl-media.com/lodging/1000000/20000/19500/19467/169f18e6_y.jpg) ### The Pfister Hotel 10/10 Excellent "The place is beautiful and the staf are so kind and helpful " [](https://expedia.ca/Milwaukee-Hotels-The-Pfister-Hotel.h19467.Hotel-Information) ![Wildwood Lodge](https://images.trvl-media.com/lodging/1000000/70000/62400/62392/f6965ade_y.jpg) ### Wildwood Lodge 10/10 Excellent "Great stay! The location is perfect for accessing both downtown Milwaukee and the west side. The rooms are spacious and spotless, the staff is welcoming, and the breakfast buffet offers a fresh, basic variety every morning." [](https://expedia.ca/Milwaukee-Hotels-Wildwood-Lodge.h62392.Hotel-Information) ![The Ingleside Hotel](https://images.trvl-media.com/lodging/1000000/900000/894100/894006/8211d654_y.jpg) ### The Ingleside Hotel 10/10 Excellent "Room was very nice, restaurant was wonderful, nice friendly staff." [](https://expedia.ca/Milwaukee-Hotels-The-Ingleside-Hotel.h894006.Hotel-Information) ![Sheraton Milwaukee Brookfield Hotel](https://images.trvl-media.com/lodging/1000000/10000/9500/9488/ac547b1c_y.jpg) ### Sheraton Milwaukee Brookfield Hotel 10/10 Excellent "Very clean rooms " [](https://expedia.ca/Milwaukee-Hotels-Sheraton-Milwaukee-Brookfield-Hotel.h9488.Hotel-Information) ![Hyatt Regency Milwaukee](https://images.trvl-media.com/lodging/1000000/20000/18100/18051/53781c07_y.jpg) ### Hyatt Regency Milwaukee 10/10 Excellent "The location with the skybridge to Baird center was the big stand out feature." [](https://expedia.ca/Milwaukee-Hotels-Hyatt-Regency-Milwaukee.h18051.Hotel-Information) ![Hilton Milwaukee](https://images.trvl-media.com/lodging/1000000/10000/6100/6090/cc399a7a_y.jpg) ### Hilton Milwaukee 10/10 Excellent "My only regret was not seeing the thermostat " [](https://expedia.ca/Milwaukee-Hotels-Hilton-Milwaukee-City-Center.h6090.Hotel-Information) ![Ambassador Hotel Milwaukee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/120000/117100/117078/c32357bf_y.jpg) ### Ambassador Hotel Milwaukee, Trademark Collection by Wyndham 10/10 Excellent "we love this hotel stay there multiple times and we’ll definitely go back. It’s clean. The staff is excellent and the bar is pretty cool." [](https://expedia.ca/Milwaukee-Hotels-Ambassador-Hotel-Milwaukee.h117078.Hotel-Information) ## Frequently asked questions ### What are the best hotels in Pewaukee with outdoor pools? > In addition to the outdoor pool, this hotel also offers an indoor pool, which is great for year-round swimming, and free Wi-Fi to keep everyone connected. Families will enjoy the added convenience of free self-parking and complimentary toiletries, ensuring a straightforward stay. ### How much does a hotel with outdoor pool in Pewaukee cost? ### Which Pewaukee hotels with outdoor pools are near Waukesha, WI (UES-Waukesha County)? > Families will appreciate the convenience of the hotel's free WiFi and complimentary toiletries, making their stay as effortless as possible. Moreover, with free self-parking available, you can easily explore nearby attractions without the hassle of parking fees. > > > Located just a mile from Waukesha, WI (UES-Waukesha County) airport, this hotel is perfectly situated for those looking to enjoy both the comfort of a well-rated hotel and the adventure of outdoor activities in the surrounding area. ### Is it cheaper to book flights and a hotel in Pewaukee as a package? ### How can I save on a hotel in Pewaukee with Expedia? ### Can I cancel my hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [B&B in Brookfield ](https://www.expedia.ca/Brookfield-Bed-And-Breakfast.d7083-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Condo Rentals in Brookfield ](https://www.expedia.ca/Brookfield-Condos.d7083-aaCondos.Travel-Guide-Accommodation) - [Beach Hotel Hotels in Brookfield ](https://www.expedia.ca/Brookfield-Hotels-Beach-Hotel.0-0-d7083-tBeachHotel.Travel-Guide-Filter-Hotels) - 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