Jefferson County Vacation Packages 2026 from $354

Search vacation packages deals in Jefferson County's top destinations

Giant fried mozzarella sticks. "#delicious"

Watertown

Vacations

Jefferson County flight + hotel vacation packages

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

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$354

per person

Mar 22 - Mar 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.

theWit Chicago, a Hilton Hotel

Downtown Chicago

Save 100% on your flight

$358

per person

Mar 22 - Mar 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking. Limo/town car service, WiFi in public areas, and express check-out are also on offer.

Hilton Chicago

Downtown Chicago

Save 100% on your flight

$436

per person

Mar 22 - Mar 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.

Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

Save 100% on your flight

$515

per person

Mar 22 - Mar 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, a gym, and a poolside bar. Enjoy the seasonal outdoor pool and perks like free WiFi. Self parking, a 24-hour business center, and a coffee shop are also offered.

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$474

per person

Mar 22 - Mar 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.

Top Jefferson County hotels deals

Timber Ridge Lodge and Waterpark

7020 Grand Geneva Way Lake Geneva WI

$194 nightly

$216 total

Jan 22 - Jan 23

Total with taxes and fees

This smoke-free aparthotel features a golf course, free water park access, and a full-service spa. Take advantage of ski lessons, ski rentals and ski storage on site, and enjoy downhill skiing. Bring the family and enjoy the lazy river, mini golf, and kid-friendly dining.

Pool

Hot Tub

DoubleTree by Hilton Madison East

4402 E Washington Ave Madison WI

Free Cancellation

Reserve now, pay when you stay

$106 nightly

$122 total

Jan 18 - Jan 19

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Pet friendly

Lodge Geneva National

W4240 WI-50 Lake Geneva WI

Free Cancellation

Reserve now, pay when you stay

$123 nightly

$138 total

Feb 1 - Feb 2

Total with taxes and fees

This resort features a restaurant, an indoor pool, and a bar/lounge. You'll appreciate the gym, poolside bar, and concierge services.

Pool

Pet friendly

Grand Geneva Resort & Spa

7036 Grand Geneva Wy Lake Geneva WI

$258 nightly

$288 total

Feb 7 - Feb 8

Total with taxes and fees

This smoke-free resort features a golf course, a full-service spa, and a water park. Take advantage of ski lessons, ski rentals and ski passes on site, and enjoy downhill skiing. There's fun for all ages with a children's pool and a playground, and families will appreciate the onsite laundry facilities.

Pool

Hot Tub

Lake Lawn Resort

2400 E Geneva St Delavan WI

Free Cancellation

Reserve now, pay when you stay

$133 nightly

$151 total

Jan 18 - Jan 19

Total with taxes and fees

This resort features a golf course, a full-service spa, and a marina. There's fun for all ages with a children's club and a children's pool, and supervised childcare is an added bonus. Enjoy a meal in one of the 2 restaurants and free perks like free self parking and WiFi in public areas.

Pool

Hot Tub

La Quinta Inn & Suites by Wyndham Madison American Center

5217 E Terrace Dr Madison WI

Free Cancellation

Reserve now, pay when you stay

$76 nightly

$87 total

Jan 19 - Jan 20

Total with taxes and fees

This hotel features an indoor pool and a gym. Enjoy the hot tub and free perks like continental breakfast and free self parking. A 24-hour business center, a lobby fireplace, and a communal living room are also on offer.

Pool

Hot Tub

Don't see what you're looking for?

See all available properties in Jefferson County

View all properties

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.

Photos of local treasures

Browse Jefferson County vacation photos for more inspiration

Frequently asked questions

How much are vacation packages to Jefferson County?

You can pick up an awesome flight and hotel bundle from just $354. With a Travelocity vacation package, a getaway to Jefferson County has never looked so enticing! Save some time and money and get an early start with packing your suitcases.

Where can I get the best vacation package deals for Jefferson County?

No matter your style, Travelocity can help you score the best Jefferson County package deal. The only thing you have to do is select a combination from our 400 air carriers and 1,000,000 properties worldwide.

Why should I book my Jefferson County vacation bundle via Travelocity?

Because we believe in crafting special vacation experiences. From hotels and flights to car rentals and activities, our packages make it a breeze to save. Our support team is available 24/7 to ensure you'll never wander alone. We also have a Price Match Guarantee, so you can lock in your vacation knowing you've scored the best deal around. How? If you find a lower price, we'll match it!

Can I save money on my Jefferson County car rental if I bundle it with a hotel or flight?

You sure can with our Jefferson County vacation packages. With one of these, there are lots of ways to stretch your budget further. Bundle any two or more car, flight, hotel and tour bookings and see the savings pile up. With a rental car, all the landmarks in and around Jefferson County are within reach.

Which airport is best for Jefferson County?

That depends on where you're taking off from and where you're going — General Mitchell Intl. Airport (MKE), Dane County Regional Airport (MSN) or Rockford, IL (RFD-Greater Rockford) are where you'll most likely touch down.

What is there to do in Jefferson County?

A diverse and lively destination, Jefferson County offers some terrific landmarks. Lake Koshkonong and Glacial River Bike Trail are a couple of the top picks.