Title: Book the Best Pewaukee WINERY Hotels 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 Winery Hotels Tonight [Jan 19 - Jan 20](https://www.expedia.ca/Hotel-Search?regionId=145269&startDate=2026-01-19&endDate=2026-01-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 20 - Jan 21](https://www.expedia.ca/Hotel-Search?regionId=145269&startDate=2026-01-20&endDate=2026-01-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=145269&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=145269&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Pewaukee hotels with winery ![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) ![Dining](https://images.trvl-media.com/lodging/114000000/113550000/113548100/113548005/53b54518.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113550000/113548100/113548005/0b031ed6.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) ### Stunning Brewers Hill Retreat with 2 bedrooms & 1 bath [](https://www.expedia.ca/Milwaukee-Hotels-Stunning-Brewers-Hill-Retreat-With-2-Bedrooms-1-Bath.h113548005.Hotel-Information) Brewers Hill 10/10 Exceptional (2 reviews) "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 $107 CA $361 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Milwaukee-Hotels-Stunning-Brewers-Hill-Retreat-With-2-Bedrooms-1-Bath.h113548005.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/112000000/111950000/111945700/111945649/106b3bdf_edited_ddf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/112000000/111950000/111945700/111945649/16f92a09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111950000/111945700/111945649/f846b73a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/112000000/111950000/111945700/111945649/600e9eb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2bed 1.5bath House, Lower Eastside, King Bed, Fire Pit, Sleeps 6 [](https://www.expedia.ca/Milwaukee-Hotels-2bed-15bath-House.h111945649.Hotel-Information) Downtown Milwaukee 10/10 Exceptional (1 review) "Overall had the best stay with me and my 3 kids! The house was even better than the pictures. Cute decor, comfy beds, great kitchen amenities to make your stay feel right at home. The host provided clear, easy house and parking instructions! And a grocery store is a close, 5 minute for easy shopping trips. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristen M. CA $131 CA $433 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Milwaukee-Hotels-2bed-15bath-House.h111945649.Hotel-Information) ![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) ![Interior](https://images.trvl-media.com/lodging/58000000/57810000/57800100/57800049/28e04e37.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) ![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) ### King Bed - FAST WIFI \~ Near Froedtert \~ Undergrnd Parking [](https://www.expedia.ca/Milwaukee-Hotels-Fast-Wifisanitizednear-Froedtertking-Bedunderground-Parking.h57800049.Hotel-Information) Wauwatosa 10/10 Exceptional (4 reviews) "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. [](https://www.expedia.ca/Milwaukee-Hotels-Fast-Wifisanitizednear-Froedtertking-Bedunderground-Parking.h57800049.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/20000000/19130000/19129400/19129311/71dd48d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/20000000/19130000/19129400/19129311/b6137e45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/20000000/19130000/19129400/19129311/390ca9ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books, stereo](https://images.trvl-media.com/lodging/20000000/19130000/19129400/19129311/w2168h2334x0y0-95029d65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gift yourself a getaway in 2026 [](https://www.expedia.ca/Cedarburg-Hotels-Premiere-Host-Cedarburg-Wandernhaus-In-Prime-Location-Wo-Cleaning-Fees.h19129311.Hotel-Information) Cedarburg 10/10 Exceptional (195 reviews) "Very attentive hosts, fantastic location, extremely clean and comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dennis R. CA $227 CA $284 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Cedarburg-Hotels-Premiere-Host-Cedarburg-Wandernhaus-In-Prime-Location-Wo-Cleaning-Fees.h19129311.Hotel-Information) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/51000000/50730000/50725600/50725537/e7fc70eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/51000000/50730000/50725600/50725537/5fcac9ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/51000000/50730000/50725600/50725537/70c8098d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/51000000/50730000/50725600/50725537/063edccf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fast WiFi - Underground Parking - King Bed - Near Froedtert [](https://www.expedia.ca/Milwaukee-Hotels-Sanitizedking-Bednear-Froedtertfast-Wifiunderground-Parking.h50725537.Hotel-Information) Wauwatosa 9.8/10 Exceptional (22 reviews) "Our stay at Dolphin Square was wonderful. It introduced us to Wawutosa which is a wonderful small with great places to eat - shop - walk 😊" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary Ann P. [](https://www.expedia.ca/Milwaukee-Hotels-Sanitizedking-Bednear-Froedtertfast-Wifiunderground-Parking.h50725537.Hotel-Information) ![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/51000000/50730000/50725600/50725542/1f7d14d0.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) ![Smart TV, printers](https://images.trvl-media.com/lodging/51000000/50730000/50725600/50725542/a46224dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### King Bed - Near Froedtert - Fast WiFi - Underground Parking [](https://www.expedia.ca/Milwaukee-Hotels-Near-Froedtertsanitizedfast-Wifiunderground-Parkingking-Bed.h50725542.Hotel-Information) Wauwatosa 9.2/10 Wonderful (23 reviews) "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 $93 CA $353 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Milwaukee-Hotels-Near-Froedtertsanitizedfast-Wifiunderground-Parkingking-Bed.h50725542.Hotel-Information) ![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) ![Smart TV](https://images.trvl-media.com/lodging/58000000/57810000/57800100/57800041/80351268.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) ![Smart TV](https://images.trvl-media.com/lodging/58000000/57810000/57800100/57800041/50a2f88c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### King Bed-FAST WiFi - Undrgrd Parking - Near Froedtert [](https://www.expedia.ca/Milwaukee-Hotels-SanitizedFast-WiFiNear-FroedtertKing-BedUnderground-Parking.h57800041.Hotel-Information) Wauwatosa 10/10 Exceptional (14 reviews) "Great location and Ian was very responsive to any/all questions." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tyler B. CA $93 CA $349 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Milwaukee-Hotels-SanitizedFast-WiFiNear-FroedtertKing-BedUnderground-Parking.h57800041.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/51000000/50730000/50725600/50725546/8ac564d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/51000000/50730000/50725600/50725546/721f6ddd.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) ![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) ### Underground Parking,Near Froedtert, King Bed, Fast WiFi [](https://www.expedia.ca/Milwaukee-Hotels-Near-FroedtertSanitizedKing-BedFast-WiFiUnderground-Parking.h50725546.Hotel-Information) Wauwatosa 9.4/10 Exceptional (3 reviews) "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 $93 CA $353 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Milwaukee-Hotels-Near-FroedtertSanitizedKing-BedFast-WiFiUnderground-Parking.h50725546.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=2026-02-02&endDate=2026-02-03®ionId=145269&adults=2&location_highlights_explore=winery&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 "Breakfast buffet was good. Friendly staff" [](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 "Clean room, friendly staff" [](https://expedia.ca/Milwaukee-Hotels-Saint-Kate-The-Arts-Hotel.h23253.Hotel-Information) ![Potawatomi Hotel & Casino](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474917/d47b7999_y.jpg) ### Potawatomi Hotel & Casino 10/10 Excellent "Amazing how wonderful they were during our visit. Every little touch was appreciated. Above and beyond" [](https://expedia.ca/Milwaukee-Hotels-Potawatomi-Hotel-Casino.h8474917.Hotel-Information) ![The Pfister Hotel](https://images.trvl-media.com/lodging/1000000/20000/19500/19467/169f18e6_y.jpg) ### The Pfister Hotel 10/10 Excellent "Beautiful classic hotel " [](https://expedia.ca/Milwaukee-Hotels-The-Pfister-Hotel.h19467.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 "Friendly staff. Shay was so helpful. Max, the bartender, was super cool and makes awesome drinks. Clean room. Comfy bed and pillows. Spacious fridge. Nice views of downtown. Valet staff was efficient. Recommend 100%!!! ." [](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 "Great front desk staff! Friendly and helpful! Clean and comfortable rooms! " [](https://expedia.ca/Milwaukee-Hotels-Wildwood-Lodge.h62392.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 Brewhouse Inn & Suites](https://images.trvl-media.com/lodging/8000000/7090000/7084400/7084340/c5b60965_y.jpg) ### The Brewhouse Inn & Suites 10/10 Excellent "It would be very helpful clean daily the room" [](https://expedia.ca/Milwaukee-Hotels-The-Brewhouse-Inn-Suites.h7084340.Hotel-Information) ![Hilton Milwaukee](https://images.trvl-media.com/lodging/1000000/10000/6100/6090/cc399a7a_y.jpg) ### Hilton Milwaukee 10/10 Excellent "Spotless new rooms" [](https://expedia.ca/Milwaukee-Hotels-Hilton-Milwaukee-City-Center.h6090.Hotel-Information) ## Frequently asked questions ### How much does a winery hotel in Pewaukee cost? ### Which area of Pewaukee is best to stay in for vineyards and wineries? > For couples wishing to enjoy a romantic escape, the vineyards near Pewaukee offer a ideal setting. Picture yourselves strolling through lush vineyards, sipping on award-winning wines, and perhaps even participating in a wine-tasting tour that includes delicious food pairings. The intimate atmosphere of these wineries creates an ideal backdrop for memorable moments together. > > > Families, on the other hand, may want to explore the nearby Kettle Moraine State Forest, which provides opportunities for outdoor activities and adventures. After a day of hiking and exploring, visiting a family-friendly winery that offers activities for children can be a fun way to unwind. Many local vineyards feature spacious grounds where families can picnic and enjoy the beautiful scenery, making it a wonderful day out for all ages. ### What winery activities should we do in Pewaukee? > For couples seeking a romantic outing, consider a visit to the elegant Lake Country Wine Trail. This scenic route connects multiple wineries, allowing you to savour exquisite wines while taking in the stunning lakeside views. Many wineries offer special tasting events and vineyard tours, creating an intimate atmosphere ideal for making memories together. > > > Families will also find plenty to enjoy in Pewaukee's wine scene. Some wineries host family-friendly events, including outdoor picnics and seasonal festivals, where children can play while adults enjoy wine tastings. It's a wonderful way to introduce the younger generation to the beauty of local agriculture while ensuring a fun day out for everyone. > > > Regardless of your preferences, Pewaukee's winery activities promise an enjoyable experience, combining the joys of wine with the stunning natural backdrop of Wisconsin's lake country. ### Does Pewaukee host any wine festivals or events? > For couples seeking a romantic outing, attending the festival can be a lovely way to spend a day together. Picture yourselves strolling hand in hand, sampling exquisite wines, and discovering unique art pieces. The relaxed atmosphere and beautiful surroundings create an ideal backdrop for making lasting memories. > > > Families can also enjoy the festival, as it often features kid-friendly activities and entertainment. While the parents explore the wine offerings, children can partake in crafts or face painting, ensuring everyone has a fun-filled day. ### How can I save on a winery hotel in Pewaukee with Expedia? ### Is it cheaper to book flights and a winery hotel in Pewaukee as a package deal? ### Can I cancel my winery 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) - [Boutique Hotels in Brookfield ](https://www.expedia.ca/Brookfield-Hotels-Boutique-Hotel.0-0-d7083-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Brookfield ](https://www.expedia.ca/Brookfield-Hotels-Cheap-Hotels.0-0-d7083-tCheapHotels.Travel-Guide-Filter-Hotels) - 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