Jefferson County Vacation Packages 2026 from $542

Search vacation packages deals in Jefferson County's top destinations

Historic Union Pacific railroad stone arch bridge over Turtle Creek Wisconsin

Watertown

Vacations

Jefferson County flight + hotel vacation packages

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

The Wade

Downtown Chicago

Save 100% on your flight

$542

per person

May 10 - May 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and express check-out are also provided.

Hotel Riu Plaza Chicago

Downtown Chicago

$731

per person

May 14 - May 18

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.

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$596

per person

May 14 - May 18

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A lobby fireplace, a communal living room, and express check-out are also on offer.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$680

per person

May 14 - May 18

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.

Eurostars Magnificent Mile

Downtown Chicago

Save 100% on your flight

$685

per person

May 14 - May 18

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa and a gym are featured at this boutique hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a sauna on site, and a 24-hour front desk and express check-out are also provided.

Top Jefferson County hotels deals

Timber Ridge Lodge and Waterpark

7020 Grand Geneva Way Lake Geneva WI

Free Cancellation

Reserve now, pay when you stay

$194 nightly

$216 total

Mar 12 - Mar 13

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

Wildwood Lodge

N14 W24121 Tower Place Pewaukee WI

Free Cancellation

Reserve now, pay when you stay

$84 nightly

$95 total

Mar 9 - Mar 10

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an indoor pool, and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking.

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

Mar 8 - Mar 9

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

Holiday Inn Club Vacations at Lake Geneva Resort by IHG

7036 Grand Geneva Way Lake Geneva WI

$127 nightly

$141 total

Mar 8 - Mar 9

Total with taxes and fees

This smoke-free resort features a golf course, a full-service spa, and a water park. There's fun for all ages with mini golf and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy a meal in one of the 4 restaurants and free perks like free self parking and an area shuttle.

Pool

Hot Tub

Moxy Madison Downtown

823 East Washington Ave Madison WI

Free Cancellation

Reserve now, pay when you stay

$116 nightly

$134 total

Mar 15 - Mar 16

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Valet parking, a 24-hour business center, and a snack bar/deli are also offered.

Pet friendly

Free WiFi

La Quinta Inn & Suites by Wyndham Madison American Center

5217 E Terrace Dr Madison WI

Free Cancellation

Reserve now, pay when you stay

$71 nightly

$82 total

Mar 8 - Mar 9

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

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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

Historic Jefferson County Courthouse and Clock Tower Victorian style old historical building in Port Townsend, Olympic Peninsula, Washington State

Mid-May in Wisconsin, a large oak tree leafs out as its branches create a border for a distant lone oak, both growing in a farm field.

A short distance out of the small city of Milton, WI is a neat old wood covered bridge. It provides a little used road over a small meandering stream. On this Winter day we received over a foot of snow. The white flakes and the red bridge created one of my favorite Americana photos. The tree lined snowy path provides a surreal and wintery feel.

Frequently asked questions

How much are vacation packages to Jefferson County?

You can pick up an awesome flight and hotel bundle from just $542. 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.