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 [Jan 13 - Jan 14](https://www.expedia.ca/Hotel-Search?regionId=145269&startDate=2026-01-13&endDate=2026-01-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 14 - Jan 15](https://www.expedia.ca/Hotel-Search?regionId=145269&startDate=2026-01-14&endDate=2026-01-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=145269&startDate=2026-01-16&endDate=2026-01-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=145269&startDate=2026-01-23&endDate=2026-01-25&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/d6c209b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/70000/62400/62392/3cf48ce8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/62400/62392/f6965ade.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/70000/62400/62392/b3f0c5a3.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 (1,005 reviews) "Front desk staff was so friendly and professional, location convenient and the area dining never disappoints. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rodney CA $117 CA $132 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Milwaukee-Hotels-Wildwood-Lodge.h62392.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/670000/663900/663812/b4c5d363.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/670000/663900/663812/6b221df7.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 (1,004 reviews) "Great stay over all. Staff and were helpful and friendly. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Marie-Anne CA $110 CA $124 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Milwaukee-Hotels-Best-Western-Waukesha-Grand.h663812.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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/580000/579400/579313/7138e0b3.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) ![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) ### 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 (470 reviews) "Our stay was December 20th. Vivian at the front desk on the evening shift was a delight. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Irene CA $135 CA $152 total includes taxes & fees Feb 11 - Feb 12 [](https://www.expedia.ca/Milwaukee-Hotels-Holiday-Inn-Pewaukee-Milwaukee-West.h579313.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) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/900000/894100/894006/ad50967c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/900000/894100/894006/03299826.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 (762 reviews) "Parking was easy. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dalal CA $149 CA $168 total includes taxes & fees Jan 15 - Jan 16 [](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) ![Lobby sitting area](https://images.trvl-media.com/lodging/124000000/123950000/123948300/123948214/7f0fc254.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/124000000/123950000/123948300/123948214/a64b286a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/124000000/123950000/123948300/123948214/d8472473.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 10/10 Exceptional (6 reviews) "Nice and clean room and great coffee as well!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jimmy CA $111 CA $136 total includes taxes & fees Feb 11 - Feb 12 [](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) ![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) ![Front of property](https://images.trvl-media.com/lodging/1000000/70000/67600/67577/54fd4521.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 (1,004 reviews) "Girl at front desk was very nice and the rooms where nice." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jay CA $100 CA $113 total includes taxes & fees Jan 19 - Jan 20 [](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/16000000/15730000/15723400/15723341/eb35f1bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Jetted Tub](https://images.trvl-media.com/lodging/16000000/15730000/15723400/15723341/33d7b098.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/16000000/15730000/15723400/15723341/bb0d1ecd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/16000000/15730000/15723400/15723341/325a906a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### AmericInn by Wyndham Delafield-Waukesha-Milwaukee [](https://www.expedia.ca/Milwaukee-Hotels-AmericInn-By-Wyndham-Delafield.h15723341.Hotel-Information) Delafield 8.0/10 Very good (713 reviews) "Check in went smooth and the worker was nice. The rooms were clean and nice." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jay CA $95 CA $108 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Milwaukee-Hotels-AmericInn-By-Wyndham-Delafield.h15723341.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/f17c0f1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/70000/60800/60775/472b84c8.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) ### 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 (607 reviews) "Great rooms. Really clean facilities" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Aaron CA $121 CA $137 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/Milwaukee-Hotels-Holiday-Inn-Express-Suites-Delafield.h60775.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/33000000/32510000/32501800/32501737/2b117afb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/33000000/32510000/32501800/32501737/ac1d9528.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/33000000/32510000/32501800/32501737/b3e34ba9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/33000000/32510000/32501800/32501737/1ed7a069.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Drury Plaza Hotel Milwaukee Downtown [](https://www.expedia.ca/Milwaukee-Hotels-Drury-Plaza-Hotel-Milwaukee-Downtown.h32501737.Hotel-Information) Downtown Milwaukee 9.6/10 Exceptional (2,014 reviews) "Great location and great accommodations. Family friendly and the complimentary food was great." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melanie CA $139 CA $164 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Milwaukee-Hotels-Drury-Plaza-Hotel-Milwaukee-Downtown.h32501737.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/670000/661000/660970/fb4c82e6.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) ![Room, 1 King Bed with Sofa bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/670000/661000/660970/5133c8e0.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 (571 reviews) "Pretty river on back side of property. Village of Jackson has many amenities. Staff at hotel friendly, helpful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lilia CA $117 CA $129 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Jackson-Hotels-Comfort-Inn-Suites-Jackson-West-Bend.h660970.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=2026-01-27&endDate=2026-01-28®ionId=145269&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Pewaukee Hotel Reviews ![Hyatt Regency Milwaukee](https://images.trvl-media.com/lodging/1000000/20000/18100/18051/53781c07_y.jpg) ### Hyatt Regency Milwaukee 10/10 Excellent "Very clean room great dtaffy" [](https://expedia.ca/Milwaukee-Hotels-Hyatt-Regency-Milwaukee.h18051.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 "Rooms are clean , valet parking is terrible. Many times I almost had to valet my car on my own ,because nobody was there to assist" [](https://expedia.ca/Milwaukee-Hotels-Saint-Kate-The-Arts-Hotel.h23253.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 "The decor is beautiful, the room was bigger than I imagined it would be, and the staff was very helpful. I unfortunately had a run in with another guest in the bar while watching football. The staff eventually called the police to handle this individual and staff was extremely helpful and apologetic to me, making sure my experience was still satisfying. Rest assured, we already have plans to visit again. " [](https://expedia.ca/Milwaukee-Hotels-Ambassador-Hotel-Milwaukee.h117078.Hotel-Information) ![The Iron Horse Hotel](https://images.trvl-media.com/lodging/3000000/2100000/2097200/2097106/2030b501_y.jpg) ### The Iron Horse Hotel 10/10 Excellent "Wonderful stay! " [](https://expedia.ca/Milwaukee-Hotels-The-Iron-Horse-Hotel.h2097106.Hotel-Information) ![Wildwood Lodge](https://images.trvl-media.com/lodging/1000000/70000/62400/62392/f6965ade_y.jpg) ### Wildwood Lodge 10/10 Excellent "Love the staff. I haven’t felt so relaxed in a long time. They helped me out with check in when they saw me with my 3 kids. The room service ladies were so kind,same with the guys from the breakfast. I loved the view from my window. I just had an amazing experience overall. Everything was neat and super nice breakfast. " [](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 "My husband and I had a great visit. We were able to enjoy our visit with family while staying in the hotel. Greatly enjoyed the Christmas Lights also. " [](https://expedia.ca/Milwaukee-Hotels-The-Ingleside-Hotel.h894006.Hotel-Information) ![Best Western Plus Milwaukee Airport Hotel & Conference Ctr](https://images.trvl-media.com/lodging/1000000/20000/11900/11861/9f1af6f1_y.jpg) ### Best Western Plus Milwaukee Airport Hotel & Conference Ctr 10/10 Excellent "Hotel had some dated areas, but the room was nice and clean, the staff was professional. The pool and hot tub area was spacious and inviting. I would definitely stay again for MKE." [](https://expedia.ca/Milwaukee-Hotels-Best-Western-Plus-Milwaukee-Airport-Hotel-Conference-Ctr.h11861.Hotel-Information) ![Sybaris Pool Suites Mequon](https://images.trvl-media.com/lodging/9000000/8020000/8014300/8014238/0c7c951b_y.jpg) ### Sybaris Pool Suites Mequon 10/10 Excellent "Wonderfull" [](https://expedia.ca/Milwaukee-Hotels-Sybaris-Pool-Suites-Mequon.h8014238.Hotel-Information) ![Sonesta Select Milwaukee Brookfield](https://images.trvl-media.com/lodging/1000000/30000/24800/24705/843d85ad_y.jpg) ### Sonesta Select Milwaukee Brookfield 10/10 Excellent "Clean and staff" [](https://expedia.ca/Milwaukee-Hotels-Sonesta-Select-Milwaukee-Brookfield.h24705.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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