Jefferson County Holidays from AU$963

Book a Hotel + Flight or Car together to unlock savings

Photo by Stephanie Kay

  • Plan, book, travel with confidence

    • Better together

    Save up to AU$703 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 Holiday

With a Jefferson County holiday 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 holiday. From hotels and flights, to activities and more, we know how to create a travel experience like no other.

The Latest Jefferson County Holiday Deals

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was AU$1,181, price is now AU$963 per person
AU$963
per person
23 Dec - 26 Dec
found 6 hours ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
Clean room, friendly staff, great location and within walking distance from all shops!

Reviewed on 7 Oct 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was AU$1,361, price is now AU$1,027 per person
AU$1,027
per person
23 Dec - 26 Dec
found 6 hours ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
I loved the hotel, however I would request an inside room next time. It was extremely noisy outside.

Reviewed on 11 Oct 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was AU$1,295, price is now AU$977 per person
AU$977
per person
23 Dec - 26 Dec
found 6 hours ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (291 reviews)
Food price was high but everything was fine

Reviewed on 4 Oct 2025

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was AU$1,263, price is now AU$971 per person
AU$971
per person
23 Dec - 26 Dec
found 6 hours ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (2,765 reviews)
The view from the panoramic view was amazing. The gym was comfortable and the credit to amuse was nice

Reviewed on 9 Oct 2025

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was AU$1,290, price is now AU$1,062 per person
AU$1,062
per person
23 Dec - 26 Dec
found 6 hours ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
8.6/10 Excellent! (1,920 reviews)
Fabulous suite overlooking Millenium Park and Lake Michigan. Clean, attentive staff, and good amenities. Walk to everything.

Reviewed on 10 Oct 2025

Jefferson County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
General Mitchell Intl. Airport (MKE)
Top Sights
Lake Koshkonong, Busy Barns Adventure Farm and Glacial River Bike Trail

Our pick of the best Jefferson County Hotel Deals

Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

3.5 out of 5
7020 Grand Geneva Way, Lake Geneva, WI
Fully refundableReserve now, pay when you stay
The price is AU$302 per night from 28 Oct to 29 Oct
AU$302
28 Oct - 29 Oct
includes taxes & fees
8.6/10 Excellent! (3,003 reviews)
"This is a wonderful resort. The staff are very friendly and made sure we had everything we needed. The rooms are spacious and are well supplied with the necessities. The water park is safe and clean. Lots of lifeguards. The snack bar inside the water park itself, is awesome. Johann and Emma helped ..."

Reviewed on 5 Oct 2025

Timber Ridge Lodge and Waterpark
Motel 6 Madison, WI - East

Motel 6 Madison, WI - East

2 out of 5
4202 E Towne Blvd, Madison, WI
Fully refundableReserve now, pay when you stay
The price is AU$72 per night from 4 Nov to 5 Nov
AU$72
4 Nov - 5 Nov
includes taxes & fees
6.6/10 (1,008 reviews)
"We didn't get in til 11pm Sunday I was happy when we got here to find out we could get a room on first floor"

Reviewed on 8 Oct 2025

Motel 6 Madison, WI - East
DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East

4 out of 5
4402 E Washington Ave, Madison, WI
Fully refundableReserve now, pay when you stay
The price is AU$203 per night from 19 Oct to 20 Oct
AU$203
19 Oct - 20 Oct
includes taxes & fees
9.2/10 Wonderful! (1,007 reviews)
"Stayed at only for one night, but like that I didn’t have to venture out for drinks and eats. Very nice."

Reviewed on 2 Oct 2025

DoubleTree by Hilton Madison East
See all 1,219 properties in Jefferson County
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Jefferson County holiday package cost?
Custom make your Jefferson County package from just AU$963. 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!
How do I get a cheap travel package to Jefferson County?
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 holiday package. It's that easy! From hotels and flights to tours and rental cars, Expedia makes travelling 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.
What are the top hotels in Jefferson County?
When it comes to properties in Fort Atkinson, Comfort Suites Johnson Creek Conference Centre 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.
How far in advance should I book my Jefferson County holiday?
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.
What does an Expedia Jefferson County travel package include?
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 holiday, you're in charge!
What should I know before booking a Jefferson County travel package?
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.
Can I choose my airline with a Jefferson County Expedia holiday package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines globally. Our holiday packages give you the flexibility to take your pick of available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Jefferson County holiday package?
Don't worry if you're rethinking your Jefferson County holiday 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.

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.