Title: Winslow Vacation Home Rentals from CA $368: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Winslow](https://expedia.ca/Winslow-Hotels.d553248634983150076.Travel-Guide-Hotels)[Vacation Rentals in Winslow](https://expedia.ca/Winslow-Vacation-Rentals.d553248634983150076.Travel-Guide-VacationRentals)[Winslow Car Rentals](https://expedia.ca/Car-Rentals-In-Winslow.d553248634983150076.Car-Rental-Guide)[Winslow Vacation Packages](https://expedia.ca/Winslow.d553248634983150076.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Winslow Vacation Rentals - ![](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 prices for these dates In two weeks [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248634983150076&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248634983150076&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248634983150076&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=553248634983150076&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winslow Vacation Homes ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/63000000/62960000/62954800/62954750/10bb8dea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/63000000/62960000/62954800/62954750/a394d910.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/63000000/62960000/62954800/62954750/700d8d16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/63000000/62960000/62954800/62954750/3cd90852.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Darlington 9.8/10 Exceptional (47) "Close to town. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Juanita W. CA $189 CA $398 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Darlington-Hotels-Hamilton-Goebel-House-816-E-Louisa-St-Darlington-Wi.h62954750.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/61000000/60640000/60631300/60631206/w1020h683x4y0-8776d1b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/61000000/60640000/60631300/60631206/6f68c0b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/61000000/60640000/60631300/60631206/36261d26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/61000000/60640000/60631300/60631206/w1020h683x4y0-039fd84b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Monroe 10/10 Exceptional (102) "My husband and I stayed here and were so happy we did this home was beautiful and really something special. I highly recommend the stay here! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katie B. CA $273 CA $368 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Janesville-Hotels-Mjs-Penthouse.h60631206.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/43000000/42570000/42564400/42564349/9f590fe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/43000000/42570000/42564400/42564349/d60c0a97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42570000/42564400/42564349/f9ec5ed6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/43000000/42570000/42564400/42564349/47edbf52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Elizabeth 10/10 Exceptional (4) "We had 14 people stay for a business retreat. Each had their own bedroom and bathroom. We gathered in the great room for our meeting, experienced cooking together and a ‘family dinner’ around the big table. We hiked as our activity and enjoyed a bonfire too. We went into galena one evening for dinner - just a quick 20 minute drive. We enjoyed our short stay and would consider returning." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katie L. CA $4,895 CA $8,802 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Elizabeth-Hotels-Luxury-Ranch-Compound-On-300-Acres.h42564349.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89270000/89264200/89264101/124d6be2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89270000/89264200/89264101/9072d44e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/90000000/89270000/89264200/89264101/d2791a08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, free WiFi](https://images.trvl-media.com/lodging/90000000/89270000/89264200/89264101/ead8c1c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Monroe 10/10 Exceptional (35) "Everything was very clean and welcoming. The decor was cute and cozy. Overall great stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeff Z. CA $219 CA $401 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Monroe-Hotels-Beautiful-Downtown-Home.h89264101.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/28000000/27480000/27476900/27476880/bfbf9e97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/28000000/27480000/27476900/27476880/d3f0f190.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/28000000/27480000/27476900/27476880/5cf14f1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/28000000/27480000/27476900/27476880/1714df27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Elizabeth 9.8/10 Exceptional (69) "Great hosts and a ton to do. Could have spent 2 weeks here for our family reunion and could not have done everything!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Damian W. CA $2,203 CA $3,720 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Elizabeth-Hotels-LUXURIOUS-RANCH.h27476880.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=2025-12-03&endDate=2025-12-04®ionId=553248634983150076&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Apartments [](https://www.expedia.ca/Hotel-Search?destination=Winslow%2C+Illinois%2C+United+States+of+America®ionId=553248634983150076&latLong=42.492508%2C-89.792343&adults=2&startDate=2026-02-17&d1=2026-02-17&endDate=2026-02-20&d2=2026-02-20&lodging=APARTMENT) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Winslow%2C+Illinois%2C+United+States+of+America®ionId=553248634983150076&latLong=42.492508%2C-89.792343&adults=2&startDate=2026-02-17&d1=2026-02-17&endDate=2026-02-20&d2=2026-02-20&lodging=CABIN) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Winslow%2C+Illinois%2C+United+States+of+America®ionId=553248634983150076&latLong=42.492508%2C-89.792343&adults=2&startDate=2026-02-17&d1=2026-02-17&endDate=2026-02-20&d2=2026-02-20&lodging=COTTAGE) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Winslow%2C+Illinois%2C+United+States+of+America®ionId=553248634983150076&latLong=42.492508%2C-89.792343&adults=2&startDate=2026-02-17&d1=2026-02-17&endDate=2026-02-20&d2=2026-02-20&lodging=VACATION_HOME) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinslow-Private-Vacation-Homes.d553248634983150076-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinslow-Private-Vacation-Homes.d553248634983150076-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Winslow Hotel Reviews ![Country Inn & Suites by Radisson, Freeport, IL](https://images.trvl-media.com/lodging/1000000/30000/28000/27974/9cdfac50_y.jpg) ### Country Inn & Suites by Radisson, Freeport, IL 10/10 Excellent "Great staff." [](https://expedia.ca/Rockford-Hotels-Country-Inn-Suites-By-Radisson.h27974.Hotel-Information) ![3 Bedroom, 3.5 bath house in The Galena Territory.](https://images.trvl-media.com/lodging/31000000/30750000/30748600/30748536/b40a1091_y.jpg) ### 3 Bedroom, 3.5 bath house in The Galena Territory. 10/10 Excellent "There wasn’t anything we didn’t like about the place! It was spacious, clean, and not far from the downtown area. We would definitely stay there again!" [](https://expedia.ca/Galena-Hotels-3-Bedroom.h30748536.Hotel-Information) ![Darlington Inn](https://images.trvl-media.com/lodging/3000000/2180000/2173600/2173504/71192067_y.jpg) ### Darlington Inn 10/10 Excellent "The room was very clean and lots of room to move around." [](https://expedia.ca/Dodgeville-Hotels-Darlington-Inn.h2173504.Hotel-Information) ![Super 8 by Wyndham Monroe WI](https://images.trvl-media.com/lodging/1000000/460000/459900/459802/b2846b8b_y.jpg) ### Super 8 by Wyndham Monroe WI 10/10 Excellent "Room was spotless. Staff was friendly. Very quiet night! Good coffee!" [](https://expedia.ca/Janesville-Hotels-Super-8-By-Wyndham-Monroe-WI.h459802.Hotel-Information) ![3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe](https://images.trvl-media.com/lodging/35000000/34180000/34172000/34171995/962ea163_y.jpg) ### 3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe 10/10 Excellent "Nice and clean. Close to town, but out in the country with a beautiful backyard with a fire pit." [](https://expedia.ca/Monticello-Hotels-3-Bedroom.h34171995.Hotel-Information) ![Country Inn & Suites by Radisson, Stockton, IL](https://images.trvl-media.com/lodging/1000000/930000/922200/922179/0f2b2093_y.jpg) ### Country Inn & Suites by Radisson, Stockton, IL 10/10 Excellent "Great service. Came early and room was ready " [](https://expedia.ca/Galena-Hotels-Country-Inn-Suites-By-Radisson.h922179.Hotel-Information) ![AmericInn by Wyndham Monroe](https://images.trvl-media.com/lodging/1000000/670000/663100/663056/06c4b31c_y.jpg) ### AmericInn by Wyndham Monroe 10/10 Excellent "Would stay again! " [](https://expedia.ca/Janesville-Hotels-AmericInn-By-Wyndham-Monroe.h663056.Hotel-Information) ![Beautiful compound, 10 mile views, on 300 acre ranch, next to Galena Territory](https://images.trvl-media.com/lodging/31000000/30780000/30777000/30776957/f55ba580_y.jpg) ### Beautiful compound, 10 mile views, on 300 acre ranch, next to Galena Territory 10/10 Excellent "We held a surprise birthday party with extended family. Excellent property for our stay. We would absolutely come back. " [](https://expedia.ca/Elizabeth-Hotels-Beautiful-Compound.h30776957.Hotel-Information) ![Baymont by Wyndham Freeport](https://images.trvl-media.com/lodging/1000000/570000/565200/565130/89a0a36f_y.jpg) ### Baymont by Wyndham Freeport 10/10 Excellent "I loved this place. All the little extras got my attention. Very clean. A little surprise of a little duck sitting in bathroom. Loved the seasonal creamers available for coffee. Breakfast was hot and there was a variety. Staff were great." [](https://expedia.ca/Rockford-Hotels-Baymont-By-Wyndham-Freeport.h565130.Hotel-Information) ## Find out more about Winslow ## Winslow Vacation Homes information | Number of reviews | 251 | | --- | --- | | Accommodation | 46 Vacation Homes | | Lowest Price | CA $368 | | Highest Price | CA $8,802 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Hotels near Apple Canyon Lake](https://www.expedia.ca/Apple-Canyon-Lake-Hotels.0-l553248635975876542-0.Travel-Guide-Filter-Hotels) - [Farmstay in Apple River](https://www.expedia.ca/Apple-River-Agritourism.d6345756-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Apple River](https://www.expedia.ca/Apple-River-Apart-Hotels.d6345756-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Apple River](https://www.expedia.ca/Apple-River-Bed-And-Breakfast.d6345756-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels near Apple River Canyon State Park](https://www.expedia.ca/Apple-River-Canyon-State-Park-Hotels.0-l553248621532649479-0.Travel-Guide-Filter-Hotels) - 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