Name: DoubleTree by Hilton Madison East
Price range: $95 total
Rating: 9.2

Your Jefferson County Vacation

With a Jefferson County vacation package, you can forget about planning stresses and simply focus on experiencing what this wonderful destination has on offer. A trip to Jefferson County wouldn't be complete without spending some time in its most renowned cities, starting with Fort Atkinson. A couple of the top attractions here include Jefferson County Fairgrounds and Lake Koshkonong. Watertown is another favorite with Jefferson County travelers. Visitors to this exciting city love The Gobbler Theater and Holzhueter Farm State Park. Expedia has everything you need for planning your Jefferson County vacation. From hotels and flights, to activities and more, we know how to create a travel experience like no other.

Top destinations in Jefferson County

A short distance out of the small city of Milton, WI is a neat old wood covered bridge. It provides a little used road over a small meandering stream. On this Winter day we received over a foot of snow. The white flakes and the red bridge created one of my favorite Americana photos. The tree lined snowy path provides a surreal and wintery feel.

The Latest Jefferson County Vacation Packages

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

Pendry Chicago

Downtown Chicago

Save 100% on your flight

$164

per person

Jan 24 - Jan 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

18.8/10 Exceptional! (1,130 reviews)

Really great spot in the city right in the middle like a five minute walk to to everything around you the staff was great. The rooms were beautiful.

Reviewed on Nov 24, 2025

The Westin Michigan Avenue Chicago

Downtown Chicago

$456

per person

Dec 27 - Dec 31

found 24 hours ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

17.6/10 Exceptional! (1,075 reviews)

Great staff. Great location.

Reviewed on Nov 24, 2025

The Emily Hotel

Downtown Chicago

$729

per person

Dec 27 - Jan 2

found 5 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

18.4/10 Exceptional! (1,264 reviews)

Clean, quiet and comfortable room, courteous staff. We received a $25k food credit through Expedia and got exceptional pastries and coffee at the adjacent cafe.

Reviewed on Nov 22, 2025

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$680

per person

Dec 27 - Jan 2

found 1 hour ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

18/10 Exceptional! (380 reviews)

Property was clean, centrally located with wonderful staff. Will definitely stay again.

Reviewed on Nov 9, 2025

Delta Hotels by Marriott Chicago Willowbrook

Save 100% on your flight

$342

per person

Dec 25 - Jan 3

found 4 hours ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

16.4/10 Exceptional! (501 reviews)

Very clean nice rooms

Reviewed on Nov 9, 2025

Find the Best Jefferson County Vacation Packages

Jefferson County Essential Information

Language	English
Currency	U.S dollars
Closest Airport	General Mitchell Intl. Airport (MKE)
Top Sights	Lake Koshkonong, Busy Barns Adventure Farm and Palmyra Beach

Jefferson County Hotel Deals

Timber Ridge Lodge and Waterpark

7020 Grand Geneva Way Lake Geneva WI

Fully refundableReserve now, pay when you stay

$194 nightly

$216 total

Nov 30 - Dec 1

Total with taxes and fees

8.6/10 Excellent! (3,039 reviews)

Yes the room was clean nice and cozy

Reviewed on Nov 17, 2025

Motel 6 Madison, WI - East

4202 E Towne Blvd Madison WI

Fully refundableReserve now, pay when you stay

$45 nightly

$52 total

Dec 8 - Dec 9

Total with taxes and fees

6.6/10 (1,000 reviews)

Very qu

Reviewed on Nov 12, 2025

DoubleTree by Hilton Madison East

4402 E Washington Ave Madison WI

Fully refundableReserve now, pay when you stay

$83 nightly

$95 total

Nov 27 - Nov 28

Total with taxes and fees

9.2/10 Wonderful! (1,014 reviews)

Beautiful hotel with all the extra touches, such as towels shaped like animals in the room, flower on the toilet paper and very comfortable beds. The price was good for the quality of the property.

Reviewed on Nov 20, 2025

See all 1,178 properties in Jefferson County

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.