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.
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $903, price is now $618 per person
$618
per person
Nov 21 - Nov 25
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 express check-out, laundry service, and valet parking. A hair salon, WiFi in public areas, and luggage storage are also on offer.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,273, price is now $777 per person
$777
per person
Nov 24 - Nov 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Stay One Chicago

Stay One Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,161, price is now $1,387 per person
$1,387
per person
Nov 24 - Nov 30
found 17 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This smoke-free hotel includes 3 restaurants, an indoor pool, and A 24-hour gym. Enjoy the seasonal outdoor pool and perks like free WiFi. You'll appreciate the hot tub, poolside bar, and coffee shop.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,316, price is now $881 per person
$881
per person
Oct 17 - Oct 20
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.
Holiday Inn Chicago North-Evanston by IHG

Holiday Inn Chicago North-Evanston by IHG

3 out of 5
Downtown Evanston
Save 100% on your flight
Price was $998, price is now $677 per person
$677
per person
Nov 24 - Nov 30
found 17 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a lobby fireplace, and express check-out are also offered.

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
$146 nightly
The price is $166 total per night
$166 total
Sep 15 - Sep 16
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
$182 nightly
The price is $203 total per night
$203 total
Oct 7 - Oct 8
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
$330 nightly
The price is $368 total per night
$368 total
Sep 20 - Sep 21
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
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
$117 nightly
The price is $133 total per night
$133 total
Oct 12 - Oct 13
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
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
$45 nightly
The price is $52 total per night
$52 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
$165 nightly
The price is $183 total per night
$183 total
Sep 15 - Sep 16
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 $618. 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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