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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. A couple of the top attractions here include Jefferson County Fairgrounds and Lake Koshkonong. Watertown 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.
Price found within the past 48 hours. Click for updated prices.
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Dec 20 - Dec 23
Downtown Chicago
3 nights
8.6/10 - Excellent (1,884 reviews)
Roundtrip • Toronto (YTO) - Chicago (ORD)
YTZ - ORD • Nonstop ORD - YTZ • Nonstop
CA $819
per traveller
found 18 hours ago
Dec 19 - Dec 25
Downtown Chicago
6 nights
9.2/10 - Wonderful (1,360 reviews)
"Great location in the West Loop. The rooms are big and the beds are comfy. We’ve stayed there three times. The outdoor theatre shows great films and has an outdoor bar. Coffee shop is in the lobby. There’s not really a fun bar, but lots of places to have cocktails in the neighborhood. A lobby fireplace would be a nice addition in the lobby for cold Chicago nights."
Reviewed November 13, 2026
Roundtrip • Toronto (YTO) - Chicago (ORD)
YYZ - ORD • Nonstop ORD - YYZ • Nonstop
CA $1,159
per traveller
found 11 hours ago
Jan 29 - Feb 2
Downtown Chicago
4 nights
9.8/10 - Exceptional (1,000 reviews)
Roundtrip • Toronto (YYZ) - Chicago (ORD)
YYZ - ORD • Nonstop ORD - YYZ • Nonstop
CA $1,610
per traveller
found 1 day ago
Jan 24 - Jan 26
Downtown Chicago
2 nights
9.2/10 - Wonderful (1,171 reviews)
Roundtrip • Montreal (YUL) - Chicago (ORD)
YUL - ORD • 1 stop MDW - YUL • 1 stop
CA $920
per traveller
found 21 hours ago
Jan 24 - Jan 26
Downtown Chicago
2 nights
9.6/10 - Exceptional (2,073 reviews)
"i love it"
Reviewed November 10, 2026
Roundtrip • Montreal (YUL) - Chicago (ORD)
YUL - ORD • 1 stop MDW - YUL • 1 stop
CA $1,141
per traveller
found 21 hours ago
Rating: 8.4/10 (11 reviews)
You can spend an afternoon studying the exhibits at The Octagon House during your trip to Watertown. Stroll along this family-friendly area's riverfront, or simply enjoy its restaurants.
Rating: 9.4/10 (148 reviews)
You can get tickets for a performance at Fireside Dinner Theatre on your trip to Fort Atkinson. Attend a sporting event while you're in the area, or simply enjoy its coffeehouses.
Rating: 8.8/10 (11 reviews)
Commune with nature and explore the great outdoors at Lake Koshkonong during your travels in Lake Koshkonong.
Rating: 8.6/10 (46 reviews)
Take the family on an outing to Jefferson County Fairgrounds during your trip to Jefferson. Stroll along the area's riverfront or simply enjoy its coffeehouses.
Rating: 8.8/10 (69 reviews)
You can browse for the perfect souvenirs at Johnson Creek Premium Outlets during your stay in Johnson Creek. Stroll along the area's riverfront or simply enjoy its coffeehouses.
Rating: 9.4/10 (8 reviews)
Catch an event at Perkins Stadium during your trip to Whitewater. Amble around the area's riverfront or experience its festivals.
Why not spend a carefree afternoon at Lake Ripley Park Beach during your travels in Lake Ripley? While you're in the area, wander around the parks.
Rating: 9.0/10 (2 reviews)
You can take time to visit Glacial Drumlin State Trail West during your travels to Lake Mills. Stroll along the area's riverfront or simply enjoy its coffeehouses.
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.
See all properties in Jefferson County
Custom make your Jefferson County package from just CA $819. Choose from any combination of rental cars, flights and hotels to craft the getaway you've been dreaming about for ages. Be sure to add on a few experiences or tours!
Track down flights that fit your busy schedule, add a hotel room to your booking and watch the savings rack up with a Jefferson County vacation package. It's that easy! From hotels and flights to tours and rental cars, Expedia makes traveling cheaply a cinch. And with more than 550 air carriers and 1,000,000 hotel options throughout the world to choose from, you won't be short of choice.
When it comes to properties in Fort Atkinson, Comfort Suites Johnson Creek Conference Center and Best Western Watertown are two popular options. If you're also spending time in Watertown, AmericInn by Wyndham Fort Atkinson and Days Inn by Wyndham Johnson Creek will make you feel right at home.
Reserving your flights early with Expedia means one less thing to have to worry about. Most carriers advertise tickets up to 12 months prior to departure dates. This is typically the cheapest time to book. If circumstances have left you booking late, incredible deals to Jefferson County sometimes become available just a few weeks before departure.
Hotels, flights and a cool car for all your fun road trip adventures. Simply select your preferred bundle and gain access to great discounts. Once you've made your booking, add on a few tours and experiences and watch your savings grow. When it comes to creating your Jefferson County vacation, you're in charge!
So many places to go, so many things to see. With a travel package, you'll be able to cross more of them off your list. Bundle your flights, hotels and rental cars and score big savings.
Yes — and it's easy too. Expedia has access to more than 550 partner airlines globally. Our vacation packages give you the flexibility to take your pick of available flights, hotels and activities that suit you.
Don't worry if you're rethinking your Jefferson County vacation package — you can cancel or change your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur fees from your airline, hotel or car rental company. We get that life can throw the occasional spanner in the works, so make your way to our Customer Service Portal if that occurs. When you're ready to make changes, we'll be here to help.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.