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.
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
Downtown Chicago
Price was CA $1,472, price is now CA $983 per person
CA $983
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $2,159, price is now CA $1,328 per person
CA $1,328
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,583, price is now CA $1,015 per person
CA $1,015
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $2,241, price is now CA $1,437 per person
CA $1,437
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $3,396, price is now CA $2,269 per person
CA $2,269
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip 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

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 $185 per night
CA $185
CA $240 total
Sep 7 - Sep 8
includes taxes & fees
Book a stay at this family-friendly hotel in Lake Geneva. Enjoy free WiFi, free parking, and room service. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Geneva Lake and Gary Gygax Memorial are located nearby.
Pool
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
The price is CA $194 per night
CA $194
CA $254 total
Aug 25 - Aug 26
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 Geneva Lake and Gary Gygax Memorial are located nearby.
Pool
Hot tub
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 $246 per night
CA $246
CA $328 total
Sep 7 - Sep 8
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
Holiday Inn Club Vacations at Lake Geneva Resort by IHG

Holiday Inn Club Vacations at Lake Geneva Resort by IHG

3.5 out of 5
7036 Grand Geneva Way Lake Geneva WI
Free cancellation
The price is CA $205 per night
CA $205
CA $229 total
Sep 7 - Sep 8
includes taxes & fees
Book a stay at this spa resort in Lake Geneva. Enjoy free parking, an outdoor pool, 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
Lake Lawn Resort

Lake Lawn Resort

3.5 out of 5
2400 E Geneva St Delavan WI
Free cancellation
Reserve now, pay when you stay
The price is CA $127 per night
CA $127
CA $186 total
Sep 21 - Sep 22
includes taxes & fees
Book a stay at this beach resort in Delavan. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Lake Lawn Resort Marina and Delavan Lake are located nearby.
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
The price is CA $317 per night
CA $317
CA $408 total
Sep 7 - Sep 8
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
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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 $983. 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.