Jefferson County Vacation Packages 2025/2026 from $175

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.

The Blackstone, Autograph Collection

Downtown Chicago

Save 100% on your flight

$175

per person

Feb 2 - Feb 5

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 24-hour business center and free WiFi in public areas. Self parking, a lobby fireplace, and express check-in are also offered.

Level Chicago – Old Town

Downtown Chicago

$341

per person

Feb 18 - Feb 22

found 18 hours 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.

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$184

per person

Feb 20 - Feb 22

found 17 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A business center, a picnic area, and luggage storage are also on offer.

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$740

per person

Dec 30 - Jan 4

found 23 hours 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.

Trump International Hotel & Tower Chicago

Downtown Chicago

$431

per person

Feb 2 - Feb 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

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

Dec 4 - Dec 5

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

Motel 6 Madison, WI - East

4202 E Towne Blvd Madison WI

Free Cancellation

Reserve now, pay when you stay

$42 nightly

$49 total

Dec 8 - Dec 9

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Express check-in, express check-out, and laundry facilities are also on offer.

Pet friendly

Parking included

DoubleTree by Hilton Madison East

4402 E Washington Ave Madison WI

Free Cancellation

Reserve now, pay when you stay

$90 nightly

$104 total

Nov 30 - Dec 1

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

$121 nightly

$132 total

Nov 30 - Dec 1

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

Free Cancellation

Reserve now, pay when you stay

$238 nightly

$266 total

Nov 30 - Dec 1

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

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

Nov 30 - Dec 1

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 $175. 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.