Downtown Madison Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Downtown Madison

Price found within the past 48 hours. Click for updated prices.
All Star Inn & Suites

All Star Inn & Suites

2 out of 5
Price was CA $1,372, price is now CA $1,123 per person
CA $1,123
per person
Aug 12 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Madison (MSN)
9/10 Wonderful! (757 reviews)
Clean, budget friendly, fun pool for the kids and friendly staff. We love it here!

Reviewed on Jul 2, 2026

Dellshire Resort

Dellshire Resort

3.5 out of 5
Price was CA $1,878, price is now CA $1,496 per person
CA $1,496
per person
Aug 12 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Madison (MSN)
9/10 Wonderful! (81 reviews)
The theming was amazing! We loved the music that played through the resort and all of the decor. We thought the amenities- arcade, pool, fitness center, etc- were all awesome and the room was spacious and comfortable. The food was to die for! Every staff member that we met was helpful, friendly, and kind. Cannot wait to visit again!

Reviewed on Jul 4, 2026

Amber's Inn & Suites

Amber's Inn & Suites

2 out of 5
Downtown Wisconsin Dells
Price was CA $1,477, price is now CA $1,241 per person
CA $1,241
per person
Aug 12 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Madison (MSN)
9.4/10 Exceptional! (1,005 reviews)
Very Close to Dell Boat cruise

Reviewed on Jul 2, 2026

Best Western Ambassador Inn & Suites

Best Western Ambassador Inn & Suites

2.5 out of 5
Price was CA $1,742, price is now CA $1,468 per person
CA $1,468
per person
Aug 12 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Madison (MSN)
8.6/10 Excellent! (1,004 reviews)
Very clean property

Reviewed on Jul 4, 2026

Best Western Resort Hotel & Conference Center

Best Western Resort Hotel & Conference Center

2.5 out of 5
Price was CA $1,549, price is now CA $1,328 per person
CA $1,328
per person
Aug 12 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Madison (MSN)
8.4/10 Very good! (835 reviews)
Elevators are a bit wonky but they do work.

Reviewed on Jul 1, 2026

Where to stay in Downtown Madison

Find the best Downtown Madison areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Madison
A calm lake with a city skyline in the background, surrounded by trees.

Monona

Situated on Lake Monona's southeastern shore, this Madison suburb boasts the historic Indian Mounds Park, a site on the National Register of Historic Places.

Find hotels in Monona

Downtown Madison Hotel Deals

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from Jul 5 to Jul 6
CA $168
CA $194 total
Jul 5 - Jul 6
includes taxes & fees
9.4/10 Exceptional! (3,930 reviews)
"The front desk staff was incredibly kind and helpful. I ended up getting room service for breakfast and dinner one of the days, and both were prepared deliciously. Convenient parking and spacious rooms. No complaints here!"

Reviewed on Jul 4, 2026

The Madison Concourse Hotel and Governor's Club
The Edgewater

The Edgewater

4.5 out of 5
1001 Wisconsin Place Madison WI
The price is CA $324 per night from Aug 2 to Aug 3
CA $324
CA $410 total
Aug 2 - Aug 3
includes taxes & fees
9.4/10 Exceptional! (1,006 reviews)
"Old world charm meets high end service. Food at both restaurants was wonderful. Service was top notch."

Reviewed on Jul 4, 2026

The Edgewater
DoubleTree by Hilton Madison Downtown

DoubleTree by Hilton Madison Downtown

4 out of 5
525 West Johnson Street Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $212 per night from Jul 5 to Jul 6
CA $212
CA $244 total
Jul 5 - Jul 6
includes taxes & fees
9.6/10 Exceptional! (1,006 reviews)
"Excellent location to explore Madison."

Reviewed on Jul 4, 2026

DoubleTree by Hilton Madison Downtown
See all 382 properties in Downtown Madison
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Downtown Madison vacation package cost?
Starting from an incredible CA $1,123, you can custom build your Downtown Madison package the way you want. Simply combine hotels, flights and rental cars and we'll reward you with discounts.
How do I get a cheap travel package to Downtown Madison?
Just imagine all the wonderful things you could do in Downtown Madison with a pile of extra cash in your wallet. Watch your savings stack up when you bundle your travel bookings into a Downtown Madison vacation package. You have plenty of choice when you book with Expedia too. In fact, you can pick from more than 550 air carriers and 1,000,000 hotels globally. Whether you're enjoying a break with the whole family or surprising your special someone, planning a getaway to Downtown Madison is better with a package.
How far in advance should I book my Downtown Madison vacation?
While not all air carriers advertise tickets early, you can normally look up international flights on Expedia up to 12 months in advance. This is the time you can nab some incredible deals. If you're booking at the last minute, you might still be in luck. Sometimes the lowest prices emerge only weeks prior to departure.
What does an Expedia Downtown Madison travel package include?
Hotels, rental cars and flights, or any combination of them — the choice is yours. Whether you're venturing to Downtown Madison on a family road trip or traveling with your friends, there's a package to match your budget and style. Once you've made your booking, why not add on some tours or activities?
What should I know before booking a Downtown Madison travel package?
Booking all the parts of your getaway together is a smart way to save. Combine your flights, car rentals and hotels into one little package. But you're not limited to hotels. Expedia has all kinds of properties, including vacation rentals like mountain cabins and city apartments. You've got loads of choices!
Can I choose my airline with a Downtown Madison Expedia vacation package?
Yes, definitely. Expedia has over 550 airline partners to choose from across the world. With so many choices, finding the perfect carrier to whisk you away to Downtown Madison won't be difficult.
If I'm not able to travel, can I cancel my Downtown Madison vacation package?
Your situation can change unexpectedly, so yes. You may be able to change or cancel your Downtown Madison vacation package at no cost if you've booked in the last 24 hours. For older bookings, you can still make changes, but your car rental company, airline or hotel may impose a fee. Looking for more information? Have a look at our Customer Service Portal. We'll help make sure your trip goes off without a hitch.

Stay near popular Downtown Madison attractions

A large white building with a dome and columns, surrounded by trees and a flower bed.
Photo by Liz Roy
Open Photo by Liz Roy

Capitol Square

9.4/10 (1,420 reviews)
You can find out about the history of Madison with a visit to Capitol Square. Visit the area's shops, or simply enjoy its restaurants.
See properties

Things to do

Murmurs of Mourning & Murder: Madison Ghost Tour

Murmurs of Mourning & Murder: Madison Ghost Tour

CA $44
per adult
Murmurs of Mourning & Murder: Madison Ghost Tour
Downtown Madison Sightseeing & History with Self-Guided Audio Tour

Downtown Madison Sightseeing & History with Self-Guided Audio Tour

CA $14
per traveller
100% of travellers recommend
Downtown Madison Sightseeing & History with Self-Guided Audio Tour
Downtown Madison Sightseeing & History with Self-Guided Audio Tour

Downtown Madison Sightseeing & History with Self-Guided Audio Tour

CA $15
per traveller
100% of travellers recommend
Downtown Madison Sightseeing & History with Self-Guided Audio Tour
See all activities in Madison
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.