Title: Hollandale Vacation Packages & Trips 2025/2026 from CA $653 | Expedia.ca [Hotels in Hollandale](https://expedia.ca/Hollandale-Hotels.d553248634983308021.Travel-Guide-Hotels)[Vacation Rentals in Hollandale](https://expedia.ca/Hollandale-Vacation-Rentals.d553248634983308021.Travel-Guide-VacationRentals)[Hollandale Car Rentals](https://expedia.ca/Car-Rentals-In-Hollandale.d553248634983308021.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Hollandale Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### Your Hollandale Vacation Lock in a Hollandale vacation package and get set to experience everything this city has to offer. Consider staying in the neighborhood of Downtown Mineral Point, which is good for bars and pubs, dining and history. Fill your trip to Hollandale with tours of some of its big-hitting attractions. Where to first? Don't miss [Nick Engelberts Grandview](https://www.expedia.ca/Nick-Engelberts-Grandview-Hollandale.d553248621532659024.Vacation-Attraction). Expedia is here to help you escape your daily routine. Tailor your vacation to Hollandale to suit your travel style, whatever that may be. ## Top Hollandale Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago CA $653 per person Jan 22 - Jan 26 found 9 hours ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (1,110 reviews) We loved the Pendry! Reviewed on Oct 27, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-22/2026-01-26/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=RJ5_wbqy5uZlNCDNol6qSR1M1aqSnl03Oie5BwCz0CphBI8PWTJBCetZ2_XiiK9r) ![The Westin Michigan Avenue Chicago](https://images.trvl-media.com/lodging/1000000/30000/21100/21055/dcfbf36b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Michigan Avenue Chicago Downtown Chicago CA $819 per person Dec 27 - Dec 31 found 22 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 8.8/10 Excellent! (1,070 reviews) Great trip! Will stay again. Reviewed on Nov 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-27/2025-12-31/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21055&paandie=true&dealMarker=PHEtHAqLlHxy01HQpPCW1E2u9WjV_T8wxZgf4aPB6oV6lDNDXshZoPeoE7xqnrJI) ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago CA $1,183 per person Dec 26 - Jan 2 found 13 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (367 reviews) This was our first time at Level Chicago -Old Town. Last year we stayed at Level Chicago - North. Both apartments were really cozy and offered amazing views of the city. Old Town is a great place to stay, the staff overall was professional and polite. The unit was mostly clean, however, some of the towel were stained (seemed like he make up did not come off with bleach). It wasn't to my liking so I did not use them. Also, they knew we were six people but only gave 4 bath towels. I had to request additional. Another thing is that the locks in the bathroom and bedrooms were not working. It was a bit frustrating considering 6 people were sharing one bathroom. The apartment itself is very comfortable, has washer and dryer on site, which is convenient, especially when staying with children. The kitchen was equipped with all the basic needs except a good coffee machine. They have a nespresso machine but I would have rather an actual coffee machine not espresso machine. Safety was key. My family and I felt safe in the building and the area. Parking was not available in the building (the cost is $70 per night) but that wasnt an issue because we found plenty of parking right outside by the meters. Reviewed on Oct 29, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&dealMarker=Br8uQJZB120LWEepv4T_RbMvCMdrZo-7_Sdc5-LmZB3v8-DT5T6CiYdWSV8kVFsi) ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago CA $1,395 per person Dec 12 - Dec 16 found 12 hours ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 9.6/10 Exceptional! (1,006 reviews) This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend! Reviewed on Oct 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-12/2025-12-16/?FromAirport=YYC&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&dealMarker=y6XgmfqO1e9aS9tso3yZN4Q2nk5EmtPNJgsxg3AsrtBKOOIL6IxpGdDZdVRF54v5) ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago CA $871 per person Dec 29 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,248 reviews) Always a great stay! Staff are great and rooms present great value. Reviewed on Nov 1, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&dealMarker=QL68iia_YMJweBPBpyzM-PPZFSsmK4Ugcs8Vim9aLkHsJnZJtSkjCr2qU6o4HkiD) ## Ready to book your vacation to Hollandale? Choose your dates ## Hollandale Hotel Deals ![One-of-a-kind house on 240 acres w/ prairie, woods & trout-stream - pet-friendly](https://images.trvl-media.com/lodging/75000000/74440000/74432100/74432024/c17bc4a7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### One-of-a-kind house on 240 acres w/ prairie, woods & trout-stream - pet-friendly Hollandale 10/10 Exceptional! (56 reviews) We loved our stay, particularly the miles of hiking on the farm’s trails! The property has a wonderful mix of prairie, woods, hills and valleys to explore. Thoughtful touches all over the home, we felt truly welcomed! We hope to be back soon. Reviewed on Oct 13, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=17%2F11%2F2025&endDate=18%2F11%2F2025&selected=74432024&PinnedHotelID=74432024&HadPinnedHotel=true®ionId=553248634983308021) [](https://expedia.ca/Hotel-Search?startDate=17%2F11%2F2025&endDate=18%2F11%2F2025&selected=74432024&PinnedHotelID=74432024&HadPinnedHotel=true®ionId=553248634983308021) ![Hampton Inn & Suites Madison-West](https://images.trvl-media.com/lodging/3000000/2140000/2135000/2134982/w3835h2385x4y4-ff0bb2ca_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn & Suites Madison-West 483 Commerce Dr, Madison, WI Fully refundableReserve now, pay when you stay CA $102 CA $118 total Dec 1 - Dec 2 includes taxes & fees 9/10 Wonderful! (1,000 reviews) Short stay was fine. Reviewed on Oct 27, 2025 [](https://expedia.ca/Hotel-Search?startDate=01%2F12%2F2025&endDate=02%2F12%2F2025&selected=2134982&PinnedHotelID=2134982&HadPinnedHotel=true®ionId=553248634983308021) ![Tru by Hilton Madison West, WI](https://images.trvl-media.com/lodging/23000000/22170000/22166300/22166216/dd80421a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Tru by Hilton Madison West, WI 8102 Watts Rd., Madison, WI Fully refundableReserve now, pay when you stay CA $104 CA $120 total Nov 23 - Nov 24 includes taxes & fees 9.4/10 Exceptional! (1,005 reviews) Clean room, good breakfast Reviewed on Oct 31, 2025 [](https://expedia.ca/Hotel-Search?startDate=23%2F11%2F2025&endDate=24%2F11%2F2025&selected=22166216&PinnedHotelID=22166216&HadPinnedHotel=true®ionId=553248634983308021) [See all 146 properties in Hollandale](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=04%2F11%2F2025&endDate=05%2F11%2F2025®ionId=553248634983308021) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)