Jefferson County Vacation Packages 2026 from $615

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 Westin Chicago Lombard

Save 100% on your flight

$615

per person

Aug 1 - Aug 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This smoke-free hotel includes 2 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.

The Wade

Downtown Chicago

Save 100% on your flight

$954

per person

Jun 18 - Jun 23

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$918

per person

Jun 18 - Jun 23

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$647

per person

Jul 17 - Jul 20

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$986

per person

Jul 2 - Jul 5

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

Top Jefferson County hotels deals

Harbor Shores on Lake Geneva

300 Wrigley Dr Lake Geneva WI

Free Cancellation

Reserve now, pay when you stay

$121 nightly

$137 total

May 17 - May 18

Total with taxes and fees

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

Pool

Parking included

Timber Ridge Lodge and Waterpark

7020 Grand Geneva Way Lake Geneva WI

Free Cancellation

Reserve now, pay when you stay

$171 nightly

$191 total

May 20 - May 21

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

$98 nightly

$113 total

May 17 - May 18

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

The Cove Of Lake Geneva

111 Center St Lake Geneva WI

Free Cancellation

Reserve now, pay when you stay

$144 nightly

$160 total

May 17 - May 18

Total with taxes and fees

2 hot tubs, an indoor pool, and a gym are all featured at this hotel. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the onsite laundry facilities. Traveling on business? Take advantage of the express check-out and free internet in public areas.

Pool

Hot Tub

Holiday Inn Club Vacations at Lake Geneva Resort by IHG

7036 Grand Geneva Way Lake Geneva WI

Free Cancellation

$114 nightly

$127 total

May 17 - May 18

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

Lake Lawn Resort

2400 E Geneva St Delavan WI

Free Cancellation

Reserve now, pay when you stay

$143 nightly

$162 total

May 17 - May 18

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

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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.

Frequently asked questions

How much are vacation packages to Jefferson County?

You can pick up an awesome flight and hotel bundle from just $615. 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.