Shorewood Hills Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

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

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

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Top Holiday Package Deals in Shorewood Hills

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 $1,070, price is now CA $958 per person
CA $958
per person
Aug 18 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Madison (MSN)
9/10 Wonderful! (763 reviews)
Nice place. The room we were in was renovated and looked nice. My only complaint is there is a window in the back of the room by the ceiling with no curtain so it got very light in the room early in the morning, which kept waking me up. Kids enjoyed the outdoor pool. And we enjoyed the waterpark passes. Will look to stay here again!

Reviewed on Jul 7, 2026

Dellshire Resort

Dellshire Resort

3.5 out of 5
Price was CA $1,499, price is now CA $1,267 per person
CA $1,267
per person
Aug 18 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Madison (MSN)
8.8/10 Excellent! (96 reviews)
Next. year

Reviewed on Jul 8, 2026

Amber's Inn & Suites

Amber's Inn & Suites

2 out of 5
Downtown Wisconsin Dells
Price was CA $1,185, price is now CA $1,043 per person
CA $1,043
per person
Aug 18 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Madison (MSN)
9.4/10 Exceptional! (1,003 reviews)
The bed in our room was very uncomfortable.It seemed to sink in the middle.One of our questions was how was your kitchenette? We didn't have a kitchenette don't know if they have any rooms like that?

Reviewed on Jul 8, 2026

Best Western Ambassador Inn & Suites

Best Western Ambassador Inn & Suites

2.5 out of 5
Price was CA $1,399, price is now CA $1,238 per person
CA $1,238
per person
Aug 18 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Madison (MSN)
8.6/10 Excellent! (1,005 reviews)
Everything was fine, I have nothing to complain about

Reviewed on Jul 6, 2026

Baraboo RV Resort

Baraboo RV Resort

2 out of 5
Price was CA $1,086, price is now CA $1,000 per person
CA $1,000
per person
Aug 18 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Madison (MSN)
10/10 Exceptional! (7 reviews)
Showers and bathrooms could have been a little cleaner.

Reviewed on Jul 5, 2026

Where to stay in Shorewood Hills

Find the best Shorewood Hills areas and neighborhoods for the activities you enjoy most. Learn more about Shorewood Hills
A large domed building surrounded by modern cityscape and a body of water.

Downtown Madison

4 out of top 10 points of interest in this area

The ample dining options and fantastic lake views are top of the list for many visitors to Downtown Madison. A stop by Orpheum Theater or Overture Center for the Arts might round out your trip.

Find hotels in Downtown Madison

Shorewood Hills 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
The price is CA $175 per night from Jul 12 to Jul 13
CA $175
CA $202 total
Jul 12 - Jul 13
includes taxes & fees
9.4/10 Exceptional! (3,968 reviews)
"Parking was confusing"

Reviewed on Jul 9, 2026

The Madison Concourse Hotel and Governor's Club
Best Western Plus InnTowner Madison

Best Western Plus InnTowner Madison

3 out of 5
2424 University Avenue Madison WI
The price is CA $147 per night from Jul 12 to Jul 13
CA $147
CA $170 total
Jul 12 - Jul 13
includes taxes & fees
9.2/10 Wonderful! (1,012 reviews)
"Great stay overall but seemed a little expensive for the quality of hotel."

Reviewed on Jul 8, 2026

Best Western Plus InnTowner Madison
Baymont by Wyndham Madison West/Middleton WI West

Baymont by Wyndham Madison West/Middleton WI West

2.5 out of 5
8102 Excelsior Dr Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $98 per night from Jul 12 to Jul 13
CA $98
CA $113 total
Jul 12 - Jul 13
includes taxes & fees
8/10 Very good! (1,353 reviews)
"Staff are friendly"

Reviewed on Jul 8, 2026

Baymont by Wyndham Madison West/Middleton WI West
See all 389 properties in Shorewood Hills
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 Shorewood Hills vacation package cost?
The cheapest Shorewood Hills vacation package is CA $958, so your dream vacation can become a reality — without a hefty price tag. Combine flights, hotels, car rentals and more to custom build a package that matches your travel style.
How do I get a cheap travel package to Shorewood Hills?
One of the easiest ways to save dollars (and time) is to bundle your bookings with Expedia. Hotels, flights, rental cars and activities — we've got them all. Pick and choose a combination that suits your style and watch your savings grow. We know a travel package is never a one-size-fits-all. That's why Expedia offers over 550 airlines and 1,000,000 hotels around the globe, which lets you customize your Shorewood Hills adventure.
Where should I stay in Shorewood Hills?
Urban explorers come from far and wide to see University of Wisconsin-Madison and Camp Randall Stadium in Shorewood Hills. Book a hotel within walking distance of these terrific attractions and visit them whenever you want.
How far in advance should I book my Shorewood Hills vacation?
To bag rock-bottom prices, book ASAP. Air carriers usually advertise flights, along with some of the lowest fares, up to 12 months prior to departure. Hotels, activities and car rental should also be booked early to avoid disappointment. If you were hoping for a last-minute getaway to Shorewood Hills, there are always plenty of great bargains to be had on Expedia. Book something in today!
What does an Expedia Shorewood Hills travel package include?
From hotels and airfares to car rentals, Expedia can help you create a Shorewood Hills package that suits you. Heading away for a few weeks? Consider a rental car, hotel and flight bundle. If you can only squeeze in a quick getaway, a hotel and flight deal could be more your style. Activities can also be added after you've booked. Our vacation packages make it a cinch to plan and save.
What should I know before booking a Shorewood Hills travel package?
An Expedia travel package can be customized for your circumstances and is a great way to make your hard-earned dollars stretch further. How much you include is totally up to you. Hotels, rental cars and flights — decide on a combination that suits your plans.
Can I choose my airline with a Shorewood Hills Expedia vacation package?
Yes, you sure can. Expedia has access to more than 550 airline partners throughout the world, so select the carrier that best suits your needs.
If I'm not able to travel, can I cancel my Shorewood Hills vacation package?
It's difficult to predict what tomorrow might bring, so it's comforting to know that you can change or cancel your Shorewood Hills vacation package. If you booked in the last 24 hours, you may be eligible for a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Check our Customer Service Portal for further details.

Stay near popular Shorewood Hills attractions

First Unitarian Society Meeting House

You can learn about the history of Madison with a visit to First Unitarian Society Meeting House. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.
See properties

Things to do

Murmurs of Mourning & Murder: Madison Ghost Tour

Murmurs of Mourning & Murder: Madison Ghost Tour

CA $45
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 $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.