Jefferson County Holidays

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Top destinations in Jefferson County

FlightsFlightsHotelsHotels

Fort Atkinson

Fort Atkinson

Top Flight + Hotel Deals in Jefferson County

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was €674, price is now €395 per person
€395
per person
20 Nov - 25 Nov
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (1,826 reviews)
I wish that all the staff was more accommodating! some of them were some were not!

Reviewed on 6 Oct 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was €815, price is now €456 per person
€456
per person
20 Nov - 25 Nov
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
The bed was extremly comfortable Staff was very attentive. Highly recommend

Reviewed on 7 Oct 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €1,875, price is now €1,050 per person
€1,050
per person
20 Nov - 25 Nov
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses.

Reviewed on 6 Oct 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was €1,051, price is now €608 per person
€608
per person
20 Nov - 25 Nov
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
I stayed here for one night for business travel. The room was huge. Great mini bar options. I had a nice breakfast at the restaurant.

Reviewed on 10 Oct 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was €708, price is now €437 per person
€437
per person
20 Nov - 25 Nov
found 1 day ago
Return flight included
Boston (BOS) 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

Top hotels in Jefferson County

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 €168 per night from 2 Nov to 3 Nov
€168
2 Nov - 3 Nov
includes taxes & fees
8.6/10 Excellent! (3,006 reviews)
"Loved the two bedroom suite."

Reviewed on 10 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 €40 per night from 3 Nov to 4 Nov
€40
3 Nov - 4 Nov
includes taxes & fees
6.6/10 (1,003 reviews)
"Nice AC room. Service could improve."

Reviewed on 4 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 €113 per night from 19 Oct to 20 Oct
€113
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.

Frequently asked questions

How much does a Jefferson County holiday package cost?
Custom make your Jefferson County package from just €395. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.