Deals on vacations and trips to Jefferson County

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Vacations
Watertown

Jefferson County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago North Shore by IHG

Holiday Inn Chicago North Shore by IHG

3 out of 5
Save 100% on your flight
per person
Oct 9 - Oct 14
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 business center, free WiFi in public areas, and airport shuttle. Enjoy the gym and perks like free self parking.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 9 - Oct 12
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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 18 - Oct 20
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.

Top Jefferson County hotels deals

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
$165 nightly
The price is $187 total per night
$187 total
Sep 1 - Sep 2
Total includes 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

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
$204 nightly
The price is $228 total per night
$228 total
Sep 16 - Sep 17
Total includes 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
Lodge Geneva National

Lodge Geneva National

4 out of 5
W4240 WI-50, Lake Geneva, WI
Free Cancellation
Reserve now, pay when you stay
$147 nightly
The price is $161 total per night
$161 total
Sep 7 - Sep 8
Total includes 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
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
$152 nightly
The price is $169 total per night
$169 total
Sep 7 - Sep 8
Total includes 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
DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East

4 out of 5
4402 E Washington Ave, Madison, WI
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $136 total per night
$136 total
Aug 24 - Aug 25
Total includes 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
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
$60 nightly
The price is $69 total per night
$69 total
Aug 31 - Sep 1
Total includes 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
Don't see what you're looking for?
See all available properties in Jefferson County
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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

Photo by Eric & Kristy's Adventures
Photo by Eric & Kristy's Adventures
Photo by Eric & Kristy's Adventures
Photo by Eric & Kristy's Adventures
Photo by Matt Anderson Photography
Photo by Matt Anderson Photography
Photo by Linda ❤
Photo by Linda ❤
Photo by Linda ❤
Photo by Linda ❤

Frequently asked questions

How much are vacation packages to Jefferson County?
You can pick up an awesome flight and hotel bundle from just $580. 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.