Title: Book the Best Pewaukee WINERY Hotels in 2025 | 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) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/winery.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Pewaukee, WI from CA $292 ![](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 Winery Hotels Tonight [Oct 23 - Oct 24](https://www.expedia.ca/Hotel-Search?regionId=145269&startDate=2025-10-23&endDate=2025-10-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 24 - Oct 25](https://www.expedia.ca/Hotel-Search?regionId=145269&startDate=2025-10-24&endDate=2025-10-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=145269&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=145269&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Pewaukee Winery Hotels ![Exterior](https://images.trvl-media.com/lodging/114000000/113550000/113548100/113548005/1d91f6cc_edited_af06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/114000000/113550000/113548100/113548005/2adff4b0_edited_b502.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113550000/113548100/113548005/98845608.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Casino](https://images.trvl-media.com/lodging/114000000/113550000/113548100/113548005/485d0818_edited_5fde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning Brewers Hill Retreat with 2 bedrooms & 1 bath Brewers Hill 10/10 Exceptional (2) "The property was lovely and well equipped. The host was responsive and communicative. Great location and easy rideshare to get anywhere. Would absolutely stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nuala J. CA $71 CA $316 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Milwaukee-Hotels-Stunning-Brewers-Hill-Retreat-With-2-Bedrooms-1-Bath.h113548005.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/41000000/40900000/40895300/40895206/3134b64d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, towels, soap, toilet paper](https://images.trvl-media.com/lodging/41000000/40900000/40895300/40895206/e6177671.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/41000000/40900000/40895300/40895206/a94a9b11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/41000000/40900000/40895300/40895206/57fce162.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kegel's Inn - Studio - Classic Apartment #3 Six Points 9.4/10 Exceptional (19) "This place was as cute as expected and the bed was so comfy! Super easy to find and get in and out of it. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gina W. CA $168 CA $298 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Milwaukee-Hotels-Kegels-Inn-Studio-Classic-Apartment-3.h40895206.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/58000000/57810000/57800100/57800049/65a67608.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/58000000/57810000/57800100/57800049/a831c886.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/58000000/57810000/57800100/57800049/d0720da0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/58000000/57810000/57800100/57800049/59d7cbaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### King Bed - FAST WIFI ~ Near Froedtert ~ Undergrnd Parking Wauwatosa 10/10 Exceptional (4) "Came to the Milwaukee area for a family function and Ian’s place was perfect. Convenient to everything you need and underground parking was a nice perk. Would check his place out for any return trips." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jane H. CA $98 CA $311 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Milwaukee-Hotels-Fast-Wifisanitizednear-Froedtertking-Bedunderground-Parking.h57800049.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/20000000/19130000/19129400/19129311/0114c4bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/20000000/19130000/19129400/19129311/150a4cd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19130000/19129400/19129311/7f8fcf7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/20000000/19130000/19129400/19129311/79f9d90f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cedarburg 2 br apartment sleeps 1-6 guests in prime location on Washington Ave Cedarburg 10/10 Exceptional (187) "The place was perfectly located. Property was clean and well taken care of. Owners responded to any questions immediately. Kitchen and bathroom were well equipped. Overall a great place to stay in a beautiful town." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julia CA $235 CA $292 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Cedarburg-Hotels-Premiere-Host-Cedarburg-Wandernhaus-In-Prime-Location-Wo-Cleaning-Fees.h19129311.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/121000000/120270000/120260300/120260223/e67ba29f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/121000000/120270000/120260300/120260223/fb3c6821.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120270000/120260300/120260223/a97c6697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120270000/120260300/120260223/56da68b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relax in Style: 4BR Milwaukee Home Featuring a Private Hot Tub ¦ Family-Friendly Upper East Side 8.0/10 Very good (1) "Host was wonderful at communicating before and during our stay. The house is adorable and well decorated. A few suggested notes of improvement would be the cleanliness of the bathroom, and dishwasher/ kitchen sink had an odor , no pillowcases on the pillows and there was no laundry detergent available..However, these were all minor and did not affect our overall feeling about this listing. Thank you for the sweet experience . " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joanna M. CA $267 CA $558 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Milwaukee-Hotels-Relax-In-Style-4BR-Milwaukee-Home-Featuring-A-Private-Hot-Tub-Family-Friendly.h120260223.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/119000000/118560000/118558900/118558866/54519a1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118560000/118558900/118558866/cf0b8071.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/119000000/118560000/118558900/118558866/e4575001.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/119000000/118560000/118558900/118558866/518353a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Aire - Entire Home Cedarburg 10/10 Exceptional (3) "Very cute and clean place with great back yard for dogs and deck was nice to sit out back. Would stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erin H. CA $378 CA $654 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Cedarburg-Hotels-Country-Aire-Entire-Home.h118558866.Hotel-Information) ![Smart TV, computer monitors](https://images.trvl-media.com/lodging/75000000/74490000/74488200/74488113/83de822e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74490000/74488200/74488113/f373186b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, computer monitors](https://images.trvl-media.com/lodging/75000000/74490000/74488200/74488113/129a1dda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/75000000/74490000/74488200/74488113/2f5f7ba8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Schlitz Castle: Huge 5BR/4BA Sleeps 12 w/ Double Kitchens & Living Rooms Bay View 10/10 Exceptional (20) "It was a big beautiful home" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $1,511 CA $2,222 total includes taxes & fees Oct 24 - Oct 25 [](https://www.expedia.ca/Milwaukee-Hotels-Entire-Brick-Brewery-Building-Luxury-Family-Stays-And-Gatherings.h74488113.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/51000000/50730000/50725600/50725546/c3b7c0b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/51000000/50730000/50725600/50725546/998cc62b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/51000000/50730000/50725600/50725546/e982ba64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/51000000/50730000/50725600/50725546/e9fa4945.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Underground Parking,Near Froedtert, King Bed, Fast WiFi Wauwatosa 9.4/10 Exceptional (3) "Everything was clean when we got to the place. It's in a nice neighborhood and everyone in the building seems to be quiet and mindful of others. It is also a short ride away from groceries, gas stations, and food places." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rica P. CA $116 CA $336 total includes taxes & fees Nov 22 - Nov 23 [](https://www.expedia.ca/Milwaukee-Hotels-Near-FroedtertSanitizedKing-BedFast-WiFiUnderground-Parking.h50725546.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/58000000/57810000/57800100/57800041/87cb5891.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/58000000/57810000/57800100/57800041/7dacc375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/58000000/57810000/57800100/57800041/614506f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/58000000/57810000/57800100/57800041/ecb82b7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### King Bed-FAST WiFi - Undrgrd Parking - Near Froedtert Wauwatosa 10/10 Exceptional (12) "We drove in from canada, host was very informative and responsive with any of our issues. Location was great for us as it was right next to the highways that lead to downtown and back out of town. Would definitely stay again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven M. CA $116 CA $336 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Milwaukee-Hotels-SanitizedFast-WiFiNear-FroedtertKing-BedUnderground-Parking.h57800041.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/51000000/50730000/50725600/50725542/c6dcf9db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, printers](https://images.trvl-media.com/lodging/51000000/50730000/50725600/50725542/3350627c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/51000000/50730000/50725600/50725542/d7748a56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, printers](https://images.trvl-media.com/lodging/51000000/50730000/50725600/50725542/db56297b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### King Bed - Near Froedtert - Fast WiFi - Underground Parking Wauwatosa 9.0/10 Wonderful (22) "Great place. Great location for me. If you're visit is around Hwy 100, in West Allis or Wauwatosa this is your place." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert D. CA $106 CA $319 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Milwaukee-Hotels-Near-Froedtertsanitizedfast-Wifiunderground-Parkingking-Bed.h50725542.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=2025-11-06&endDate=2025-11-07®ionId=145269&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Pewaukee Hotel Reviews ![The Pfister Hotel](//images.trvl-media.com/lodging/1000000/20000/19500/19467/169f18e6_y.jpg) ### The Pfister Hotel 10/10 Excellent "Everything was A1 from arrival to checkout. Will definitely be back" [](https://expedia.ca/Milwaukee-Hotels-The-Pfister-Hotel.h19467.Hotel-Information) ![The Brewhouse Inn & Suites](//images.trvl-media.com/lodging/8000000/7090000/7084400/7084340/c5b60965_y.jpg) ### The Brewhouse Inn & Suites 10/10 Excellent "The property and rooms are beautiful, especially if you are a beer enthusiast as the building is the former Pabst historic brewhouse. The surrounding area takes advantage of this theme, including breweries within a stone’s throw of the hotel." [](https://expedia.ca/Milwaukee-Hotels-The-Brewhouse-Inn-Suites.h7084340.Hotel-Information) ![The Ingleside Hotel](//images.trvl-media.com/lodging/1000000/900000/894100/894006/8211d654_y.jpg) ### The Ingleside Hotel 10/10 Excellent "The hotel has a beautiful lounge and fine dining restaurant. Staff is phenomenal. There’s a indoor water park attached, though I don’t know anything about it." [](https://expedia.ca/Milwaukee-Hotels-The-Ingleside-Hotel.h894006.Hotel-Information) ![Sonesta Milwaukee West Wauwatosa](//images.trvl-media.com/lodging/2000000/1740000/1730200/1730127/aa54a792_y.jpg) ### Sonesta Milwaukee West Wauwatosa 10/10 Excellent "Amazing staff, very kind and accommodating " [](https://expedia.ca/Milwaukee-Hotels-Sonesta-Milwaukee-West-Wauwatosa.h1730127.Hotel-Information) ![Holiday Inn Express Milwaukee-West Medical Center by IHG](//images.trvl-media.com/lodging/1000000/10000/3600/3512/e76b8c70_y.jpg) ### Holiday Inn Express Milwaukee-West Medical Center by IHG 10/10 Excellent "Highly recommend " [](https://expedia.ca/Milwaukee-Hotels-Holiday-Inn-Express-Milwaukee-West-Medical-Center.h3512.Hotel-Information) ![The Iron Horse Hotel](//images.trvl-media.com/lodging/3000000/2100000/2097200/2097106/2030b501_y.jpg) ### The Iron Horse Hotel 10/10 Excellent "very cool atmosphere, but no food options" [](https://expedia.ca/Milwaukee-Hotels-The-Iron-Horse-Hotel.h2097106.Hotel-Information) ![Ambassador Hotel Milwaukee, Trademark Collection by Wyndham](//images.trvl-media.com/lodging/1000000/120000/117100/117078/c32357bf_y.jpg) ### Ambassador Hotel Milwaukee, Trademark Collection by Wyndham 10/10 Excellent "Everything was great at Ambassador. Food, drinks, service was amazing! " [](https://expedia.ca/Milwaukee-Hotels-Ambassador-Hotel-Milwaukee.h117078.Hotel-Information) ![Potawatomi Hotel & Casino](//images.trvl-media.com/lodging/9000000/8480000/8475000/8474917/d47b7999_y.jpg) ### Potawatomi Hotel & Casino 10/10 Excellent "We take the shuttle to the Brewers Game! Awesome. The Sports Bar is fabulous. Service was amazing. We really enjoyed our pressure cooked chicken dinner!" [](https://expedia.ca/Milwaukee-Hotels-Potawatomi-Hotel-Casino.h8474917.Hotel-Information) ![Hilton Milwaukee](//images.trvl-media.com/lodging/1000000/10000/6100/6090/cc399a7a_y.jpg) ### Hilton Milwaukee 10/10 Excellent "Very nice! All excellent." 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