Title: Jefferson County Vacations & Trips 2026 from CA $1,462 | Expedia.ca [Jefferson County Hotels](https://expedia.ca/Destinations-In-Jefferson-County.d553248635976433209.Hotel-Destinations)[Vacation Rentals in Jefferson County](https://expedia.ca/Destinations-In-Jefferson-County.d553248635976433209.Vacation-Rental-Destinations)[Jefferson County Car Rentals](https://expedia.ca/Destinations-In-Jefferson-County.d553248635976433209.Car-Rental-Destinations) ![](https://images.trvl-media.com/place/553248635976433209/f4c6006f-102e-4de5-9575-0a5ae31519c8.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Jefferson County 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 Jefferson County Vacation With a Jefferson County vacation package, you can forget about planning stresses and simply focus on experiencing what this wonderful destination has on offer. A trip to Jefferson County wouldn't be complete without spending some time in its most renowned cities, starting with [Fort Atkinson](https://www.expedia.ca/Fort-Atkinson.d6059836.Destination-Travel-Guides). A couple of the top attractions here include Jefferson County Fairgrounds and Lake Koshkonong. [Watertown](https://www.expedia.ca/Watertown.d56036.Destination-Travel-Guides) is another favourite with Jefferson County travellers. Visitors to this exciting city love The Gobbler Theatre and Holzhueter Farm State Park. Expedia has everything you need for planning your Jefferson County vacation. From hotels and flights, to activities and more, we know how to create a travel experience like no other. ## Top Jefferson County Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/668d065a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago - River North Downtown Chicago CA $1,462 per person May 10 - May 17 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (766 reviews) Clean room and spacious. Reviewed on Feb 18, 2026 ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago CA $1,492 per person May 10 - May 17 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Great staff, clean rooms. Great location Reviewed on Feb 21, 2026 ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/b2962364_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $1,494 per person May 10 - May 17 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (347 reviews) Room smelled like food but overall very clean, very great service and staff both night and morning shift. Reviewed on Feb 16, 2026 ![The Wade](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Wade Downtown Chicago CA $1,486 per person May 10 - May 17 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 8.4/10 Very Good! (1,444 reviews) Room was very clean would return again Reviewed on Feb 23, 2026 ![Stay One Chicago](https://images.trvl-media.com/lodging/113000000/112870000/112868000/112867973/0bd05cf3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Stay One Chicago Downtown Chicago CA $2,768 per person May 10 - May 17 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) No reviews The property was great, the room was awesome! The "Stay One Chicago" is really just a name on paper, and maybe one employee who is physically at the property. I am pretty sure that he wasn't even directly employed by the "hotel". So in a nutshell, the organization has not worked out any kind of structure for checking in other than the guy that told us to download the Door, OR the Latch app. He said that the app is very difficult to get logged into. Long story made short, we wasted the 1st 2 hours in the hotel trying to get the app (both my wife and I). The app never worked, and we finally got physical key cards from the guy working for the building. There was one small piece of paper with scan codes for restaurants, but zero property maps, rules, room cleaning, and nothing explaining how to get to, or use any of the amenities. It was the worst 1st 3 hours of a vacation that we have experienced. I still gave it a 4-star because the local people were so nice and helpful, even though helping us wasn't part of their job. The valet guys were the best, super nice, and helpful. Reviewed on Feb 10, 2026 ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_553248635976433209) ## Jefferson County Hotel Deals ![Timber Ridge Lodge and Waterpark](https://images.trvl-media.com/lodging/2000000/1050000/1043900/1043867/6d6345d6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Timber Ridge Lodge and Waterpark 7020 Grand Geneva Way Lake Geneva WI Fully refundableReserve now, pay when you stay CA $192 CA $268 total Mar 3 - Mar 4 includes taxes & fees 8.6/10 Excellent! (3,147 reviews) We always enjoy coming here! Reviewed on Feb 19, 2026 [](https://expedia.ca/Hotel-Search?startDate=03%2F03%2F2026&endDate=04%2F03%2F2026&selected=1043867&PinnedHotelID=1043867&HadPinnedHotel=true®ionId=553248635976433209) ![Motel 6 Madison, WI - East](https://images.trvl-media.com/lodging/1000000/10000/1800/1719/b06e2cee_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Motel 6 Madison, WI - East 4202 E Towne Blvd Madison WI Fully refundableReserve now, pay when you stay CA $64 CA $74 total Feb 24 - Feb 25 includes taxes & fees 6.6/10 (1,010 reviews) A Reviewed on Feb 19, 2026 [](https://expedia.ca/Hotel-Search?startDate=24%2F02%2F2026&endDate=25%2F02%2F2026&selected=1719&PinnedHotelID=1719&HadPinnedHotel=true®ionId=553248635976433209) ![Wildwood Lodge](https://images.trvl-media.com/lodging/1000000/70000/62400/62392/f6965ade_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Wildwood Lodge N14 W24121 Tower Place Pewaukee WI Fully refundableReserve now, pay when you stay 8.6/10 Excellent! (1,010 reviews) The room was clean the bed and pillows were very comfortable. Sad the pool was drained but that was not the hotels fault. We would stay again Reviewed on Feb 18, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=09%2F03%2F2026&endDate=10%2F03%2F2026&selected=62392&PinnedHotelID=62392&HadPinnedHotel=true®ionId=553248635976433209) [](https://expedia.ca/Hotel-Search?startDate=09%2F03%2F2026&endDate=10%2F03%2F2026&selected=62392&PinnedHotelID=62392&HadPinnedHotel=true®ionId=553248635976433209) [See all 1,201 properties in Jefferson County](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=24%2F02%2F2026&endDate=25%2F02%2F2026®ionId=553248635976433209) 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) ## Frequently asked questions ### How much does a Jefferson County vacation package cost? ### How do I get a cheap travel package to Jefferson County? ### What are the top hotels in Jefferson County? ### How far in advance should I book my Jefferson County vacation? ### What does an Expedia Jefferson County travel package include? ### What should I know before booking a Jefferson County travel package? ### Can I choose my airline with a Jefferson County Expedia vacation package? ### If I'm not able to travel, can I cancel my Jefferson County vacation package? \* 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