Book Exclusive Jefferson County Vacation Packages

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A lush green landscape with a wooden bridge over a small stream.

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Jefferson County flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,034, price is now CA $770 per person
CA $770
per person
Nov 16 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
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 CA $2,241, price is now CA $1,441 per person
CA $1,441
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this business-friendly hotel in Joliet. Enjoy free WiFi, 3 restaurants, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Route 66 Raceway and Harrah's Casino are located nearby.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $1,079, price is now CA $774 per person
CA $774
per person
Dec 4 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,079, price is now CA $795 per person
CA $795
per person
Dec 4 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,452, price is now CA $1,079 per person
CA $1,079
per person
Nov 28 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Top Jefferson County hotels deals

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
The price is CA $192 per night
CA $192
CA $269 total
Nov 5 - Nov 6
includes taxes & fees
Book a stay at this spa aparthotel in Lake Geneva. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lake Como and Geneva Lake are located nearby.
Pool
Hot tub
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
The price is CA $147 per night
CA $147
CA $199 total
Nov 1 - Nov 2
includes taxes & fees
Book a stay at this family-friendly hotel in Lake Geneva. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Lake Como and Geneva Lake are located nearby.
Pool
Parking included
Motel 6 Madison, WI - East

Motel 6 Madison, WI - East

2 out of 5
4202 E Towne Blvd Madison WI
Free cancellation
The price is CA $63 per night
CA $63
CA $72 total
Nov 1 - Nov 2
includes taxes & fees
Stay at this motel in Madison. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions East Towne Mall and Olbrich Botanical Gardens are located nearby.
Pet-friendly
Parking included
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
The price is CA $306 per night
CA $306
CA $397 total
Nov 2 - Nov 3
includes taxes & fees
Book a stay at this spa resort in Lake Geneva. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Lake Como and Geneva Lake are located nearby.
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
The price is CA $150 per night
CA $150
CA $174 total
Nov 1 - Nov 2
includes taxes & fees
Book a stay at this business-friendly hotel in Madison. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions East Towne Mall and Olbrich Botanical Gardens are located nearby.
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
The price is CA $183 per night
CA $183
CA $244 total
Nov 1 - Nov 2
includes taxes & fees
Book a stay at this family-friendly hotel in Lake Geneva. Enjoy an outdoor pool, 2 hot tubs, and room service. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Lake Como and Geneva Lake are located nearby.
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 CA $770. 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.