Deals on vacations and trips to Jefferson County

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A stone bridge with multiple arches over a river, surrounded by trees and grassy areas.

Watertown

Vacations
Watertown

Jefferson County flight + hotel vacation packages

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

The Glen Club

4 out of 5
Save 100% on your flight
Price was $592, price is now $406 per person
$406
per person
Dec 3 - Dec 7
found 19 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
A golf course and a restaurant are featured at this smoke-free hotel. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference space. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,086, price is now $646 per person
$646
per person
Nov 6 - Nov 8
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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,562, price is now $976 per person
$976
per person
Nov 28 - Dec 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, a business center, and a picnic area are also offered.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $858, price is now $582 per person
$582
per person
Dec 10 - Dec 14
found 6 hours ago
Roundtrip flight included
Philadelphia (PHL) 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.
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
Save 100% on your flight
Price was $713, price is now $493 per person
$493
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features 3 restaurants, a bar/lounge, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, express check-out, and luggage storage are also on offer.

Top Jefferson County hotels deals

Comfort Suites Johnson Creek Conference Center

Comfort Suites Johnson Creek Conference Center

2.5 out of 5
725 Paradise Ln Johnson Creek WI
Free Cancellation
$83 nightly
The price is $95 total per night
$95 total
Oct 18 - Oct 19
Total with taxes and fees
This hotel features 3 indoor pools and a bar/lounge. Families will appreciate the children's pool and onsite laundry facilities. Enjoy the gym and free perks like buffet breakfast and free self parking.
Pool
Breakfast included
Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
300 Wrigley Dr Lake Geneva WI
Free Cancellation
Reserve now, pay when you stay
$146 nightly
The price is $166 total per night
$166 total
Sep 29 - Sep 30
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an outdoor pool, and an indoor pool. Enjoy the gym and perks like free self parking and free WiFi. Relax with a drink at the bar/lounge and enjoy the sauna.
Pool
Parking included
Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

3.5 out of 5
7020 Grand Geneva Way Lake Geneva WI
Free Cancellation
Reserve now, pay when you stay
$169 nightly
The price is $189 total per night
$189 total
Oct 20 - Oct 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
Grand Geneva Resort & Spa

Grand Geneva Resort & Spa

4 out of 5
7036 Grand Geneva Wy Lake Geneva WI
Free Cancellation
Reserve now, pay when you stay
$287 nightly
The price is $320 total per night
$320 total
Oct 29 - Oct 30
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
Motel 6 Madison, WI - East

Motel 6 Madison, WI - East

2 out of 5
4202 E Towne Blvd Madison WI
Free Cancellation
Reserve now, pay when you stay
$50 nightly
The price is $58 total per night
$58 total
Oct 4 - Oct 5
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
The Cove Of Lake Geneva

The Cove Of Lake Geneva

3.5 out of 5
111 Center St Lake Geneva WI
Free Cancellation
Reserve now, pay when you stay
$171 nightly
The price is $191 total per night
$191 total
Oct 21 - Oct 22
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. There's a restaurant and a bar/lounge for dining and drinks, and also a seasonal outdoor pool on site.
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.

Stay near popular Jefferson County attractions

The Octagon House

8.4/10 (11 reviews)
You can spend an afternoon studying the exhibits at The Octagon House during your trip to Watertown. Stroll along this family-friendly area's riverfront, or simply enjoy its restaurants.
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Photos of local treasures

Browse Jefferson County vacation photos for more inspiration

A large red brick building with a clock tower and a central archway.
A large tree with a wide canopy in a grassy field.
A large, red brick building with multiple towers and a clock tower, featuring arched windows and stone columns.
A snow-covered landscape with a red building and a frozen stream.
A stone building with a sign reading "Cold Spring Town Hall - Community Center" and a chimney.

Frequently asked questions

How much are vacation packages to Jefferson County?
You can pick up an awesome flight and hotel bundle from just $406. 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.

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