Title: Book the Best Hotels with POOL in Oconomowoc in 2026 | Expedia.ca [Hotels in Oconomowoc](https://expedia.ca/Oconomowoc-Hotels.d9046.Travel-Guide-Hotels)[Vacation Rentals in Oconomowoc](https://expedia.ca/Oconomowoc-Vacation-Rentals.d9046.Travel-Guide-VacationRentals)[Flights to Oconomowoc](https://expedia.ca/Cheap-Flights-To-Oconomowoc.d9046.Travel-Guide-Flights)[Oconomowoc Car Rentals](https://expedia.ca/Car-Rentals-In-Oconomowoc.d9046.Car-Rental-Guide)[Oconomowoc Vacation Packages](https://expedia.ca/Oconomowoc.d9046.Destination-Travel-Guides) ![Oconomowoc, WI USA - May 17, 2021: Aerial view of Okauchee Lake area](https://images.trvl-media.com/place/9046/a73581f1-a67c-44a8-b334-20311f03bead.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Oconomowoc, WI from CA $157 - ![](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 Oconomowoc Hotels with a Pool Tonight [Dec 10 - Dec 11](https://www.expedia.ca/Hotel-Search?regionId=9046&startDate=2025-12-10&endDate=2025-12-11&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 11 - Dec 12](https://www.expedia.ca/Hotel-Search?regionId=9046&startDate=2025-12-11&endDate=2025-12-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=9046&startDate=2025-12-12&endDate=2025-12-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=9046&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Oconomowoc hotels with a pool ![Indoor pool, open 6:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1690000/1683700/1683610/0510de16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1690000/1683700/1683610/f02fd1ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1690000/1683700/1683610/182e9620.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gift shop](https://images.trvl-media.com/lodging/2000000/1690000/1683700/1683610/9236d043.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Oconomowoc [](https://www.expedia.ca/Oconomowoc-Hotels-Hilton-Garden-Inn-Oconomowoc.h1683610.Hotel-Information) Oconomowoc 9.0/10 Wonderful (655) "Excellent service and comfortable room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashley CA $139 CA $157 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Oconomowoc-Hotels-Hilton-Garden-Inn-Oconomowoc.h1683610.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/84000000/83780000/83772700/83772665/0f16d37c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/84000000/83780000/83772700/83772665/68bb0070.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/84000000/83780000/83772700/83772665/b63a4255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/84000000/83780000/83772700/83772665/0c27366f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TownePlace Suites by Marriott Oconomowoc [](https://www.expedia.ca/Oconomowoc-Hotels-TownePlace-Suites-By-Marriott-Oconomowoc.h83772665.Hotel-Information) Oconomowoc 9.2/10 Wonderful (145) "Very nice hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $161 CA $181 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Oconomowoc-Hotels-TownePlace-Suites-By-Marriott-Oconomowoc.h83772665.Hotel-Information) ![Spa](https://images.trvl-media.com/lodging/3000000/2430000/2420300/2420281/7a994e93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/3000000/2430000/2420300/2420281/d15d401f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2430000/2420300/2420281/c179f765.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/3000000/2430000/2420300/2420281/1850dcc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Staybridge Suites Milwaukee West-Oconomowoc by IHG [](https://www.expedia.ca/Oconomowoc-Hotels-Staybridge-Suites-Milwaukee-West-Oconomowoc.h2420281.Hotel-Information) Oconomowoc 9.2/10 Wonderful (827) "Great stay every time. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matt CA $143 CA $161 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Oconomowoc-Hotels-Staybridge-Suites-Milwaukee-West-Oconomowoc.h2420281.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/87000000/86310000/86309000/86308927/cf61898d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/87000000/86310000/86309000/86308927/0295f8f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/87000000/86310000/86309000/86308927/f0fa1116.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/87000000/86310000/86309000/86308927/29cbc684.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Studio | Free Breakfast. Pool. Gym [](https://www.expedia.ca/Oconomowoc-Hotels-Studio-Free-Breakfast-Pool-Gym.h86308927.Hotel-Information) Oconomowoc CA $136 CA $182 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Oconomowoc-Hotels-Studio-Free-Breakfast-Pool-Gym.h86308927.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/101000000/100600000/100593100/100593005/7c41746c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/101000000/100600000/100593100/100593005/dc313043.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/101000000/100600000/100593100/100593005/90c243bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100600000/100593100/100593005/0458fd9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Free Breakfast, Gym, Great for Business Travelers! [](https://www.expedia.ca/Oconomowoc-Hotels-Free-Breakfast.h100593005.Hotel-Information) Oconomowoc CA $162 CA $211 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Oconomowoc-Hotels-Free-Breakfast.h100593005.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/84000000/83260000/83257900/83257888/a782a390.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/84000000/83260000/83257900/83257888/d31680e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83260000/83257900/83257888/90a6f08f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/84000000/83260000/83257900/83257888/96e47fcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pool. Gym. Near Aurora Medical Center! [](https://www.expedia.ca/Oconomowoc-Hotels-Pool-Gym-Near-Aurora-Medical-Center.h83257888.Hotel-Information) Oconomowoc CA $136 CA $182 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Oconomowoc-Hotels-Pool-Gym-Near-Aurora-Medical-Center.h83257888.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/101000000/100600000/100593100/100593015/f9a5ac92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100600000/100593100/100593015/470f85b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/101000000/100600000/100593100/100593015/b76366fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/101000000/100600000/100593100/100593015/0918e79e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Free Breakfast | Great for Business Travelers! [](https://www.expedia.ca/Oconomowoc-Hotels-Free-Breakfast-Great-For-Business-Travelers.h100593015.Hotel-Information) Oconomowoc CA $267 CA $341 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Oconomowoc-Hotels-Free-Breakfast-Great-For-Business-Travelers.h100593015.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/116000000/115340000/115333300/115333254/24dbc0d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/116000000/115340000/115333300/115333254/f8729da1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/116000000/115340000/115333300/115333254/5104fa02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/116000000/115340000/115333300/115333254/4315819c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pool. Gym. Your Next Trip! [](https://www.expedia.ca/Oconomowoc-Hotels-Pool-Gym-Your-Next-Trip.h115333254.Hotel-Information) Oconomowoc CA $267 CA $341 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Oconomowoc-Hotels-Pool-Gym-Your-Next-Trip.h115333254.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/101000000/100600000/100593100/100593013/b4908a97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/101000000/100600000/100593100/100593013/677464b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100600000/100593100/100593013/8a83977a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/101000000/100600000/100593100/100593013/d26d8f88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Free Breakfast. Suite Near Aurora Medical Center! [](https://www.expedia.ca/Oconomowoc-Hotels-Free-Breakfast-Suite-Near-Aurora-Medical-Center.h100593013.Hotel-Information) Oconomowoc CA $270 CA $344 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Oconomowoc-Hotels-Free-Breakfast-Suite-Near-Aurora-Medical-Center.h100593013.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/101000000/100600000/100593100/100593007/33483394.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100600000/100593100/100593007/b79da4c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/101000000/100600000/100593100/100593007/eca6d175.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100600000/100593100/100593007/6b640bbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Free Breakfast, Pool, Hot Tub, Gym. Great Suite! [](https://www.expedia.ca/Oconomowoc-Hotels-Free-Breakfast.h100593007.Hotel-Information) Oconomowoc 4.0/10 (1) CA $196 CA $251 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Oconomowoc-Hotels-Free-Breakfast.h100593007.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=2025-12-24&endDate=2025-12-25®ionId=9046&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Oconomowoc Hotel Reviews ![Sonesta Milwaukee West Wauwatosa](https://images.trvl-media.com/lodging/2000000/1740000/1730200/1730127/aa54a792_y.jpg) ### Sonesta Milwaukee West Wauwatosa 10/10 Excellent "Front desk staff was amazing my whole 4 day stay!! Bed was super comfy!! " [](https://expedia.ca/Milwaukee-Hotels-Sonesta-Milwaukee-West-Wauwatosa.h1730127.Hotel-Information) ![Hampton Inn Milwaukee/Brookfield](https://images.trvl-media.com/lodging/1000000/10000/4800/4743/655de575_y.jpg) ### Hampton Inn Milwaukee/Brookfield 10/10 Excellent "The staff was very nice. The room was clean. Everything was a easy process " [](https://expedia.ca/Milwaukee-Hotels-Hampton-Inn-MilwaukeeBrookfield.h4743.Hotel-Information) ![Country Inn & Suites by Radisson, Milwaukee West (Brookfield), WI](https://images.trvl-media.com/lodging/1000000/430000/422900/422851/c50e99ba_y.jpg) ### Country Inn & Suites by Radisson, Milwaukee West (Brookfield), WI 10/10 Excellent "Amazing stay" [](https://expedia.ca/Milwaukee-Hotels-Country-Inn-Suites-By-Radisson.h422851.Hotel-Information) ![Embassy Suites by Hilton Milwaukee Brookfield](https://images.trvl-media.com/lodging/1000000/30000/27300/27215/d5967899_y.jpg) ### Embassy Suites by Hilton Milwaukee Brookfield 10/10 Excellent "Clean" [](https://expedia.ca/Milwaukee-Hotels-Embassy-Suites-By-Hilton-Milwaukee-Brookfield.h27215.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 "Clean room, comfortable bed. " [](https://expedia.ca/Milwaukee-Hotels-Sheraton-Milwaukee-Brookfield-Hotel.h9488.Hotel-Information) ![Staybridge Suites Milwaukee West-Oconomowoc by IHG](https://images.trvl-media.com/lodging/3000000/2430000/2420300/2420281/65aa504c_y.jpg) ### Staybridge Suites Milwaukee West-Oconomowoc by IHG 10/10 Excellent "Good value for the price. The room is was clean and the staff courteous." [](https://expedia.ca/Oconomowoc-Hotels-Staybridge-Suites-Milwaukee-West-Oconomowoc.h2420281.Hotel-Information) ![Wildwood Lodge](https://images.trvl-media.com/lodging/1000000/70000/62400/62392/f6965ade_y.jpg) ### Wildwood Lodge 10/10 Excellent "Customer Service & Hospitality was as if I was a prodigal son returning Home after almost 25 years of active service in the Military. Very warming & peaceful. Will return for a full retreat, soon!" [](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 "Staff very courteous, nicely kept property, family friendly atmosphere. " [](https://expedia.ca/Milwaukee-Hotels-The-Ingleside-Hotel.h894006.Hotel-Information) ![DoubleTree by Hilton Milwaukee - Brookfield](https://images.trvl-media.com/lodging/1000000/30000/26100/26053/fb600f8a_y.jpg) ### DoubleTree by Hilton Milwaukee - Brookfield 10/10 Excellent "Very clean " [](https://expedia.ca/Milwaukee-Hotels-DoubleTree-By-Hilton-Milwaukee-Brookfield.h26053.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Oconomowoc? ### What is there to see and do in Oconomowoc? ### When is the best time to book a hotel with a pool in Oconomowoc? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Concord Hotels ](https://www.expedia.ca/Concord-Hotels.d553248635975872372.Travel-Guide-Hotels) - [Villas in Concord ](https://www.expedia.ca/Concord-Villas.d553248635975872372-aaVillas.Travel-Guide-Accommodation) - [Boutique Hotels in Delafield ](https://www.expedia.ca/Delafield-Hotels-Boutique-Hotel.0-0-d55667-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - 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