Waterloo Vacation Packages

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Your Waterloo Vacation

When you book a Waterloo vacation package, you can relax and enjoy your adventure to the fullest. Discover the best things about this fascinating city knowing that all your travel needs have been organized before you go. Your trip to Waterloo wouldn't be complete without checking out some major attractions, like Holzhueter Farm State Park. Browse Expedia's extensive range of travel options and begin planning your ideal vacation to Waterloo now.

Top Waterloo Vacation Deals

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)
The property was clean the staff was so helpful. I had asked about a place to eat and the young lady at the front desk was knowledgeable about what was around.

Reviewed on Jul 1, 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

Ready to book your vacation to Waterloo?

 

Choose your dates

Waterloo Hotel Deals

DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East

4 out of 5
4402 E Washington Ave Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $155 per night from Jul 12 to Jul 13
CA $155
CA $180 total
Jul 12 - Jul 13
includes taxes & fees
DoubleTree by Hilton Madison East
Motel 6 Madison, WI - East

Motel 6 Madison, WI - East

2 out of 5
4202 E Towne Blvd Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $81 per night from Jul 15 to Jul 16
CA $81
CA $93 total
Jul 15 - Jul 16
includes taxes & fees
6.6/10 (1,003 reviews)
"There was a lot of loitering on the property."

Reviewed on Jul 3, 2026

Motel 6 Madison, WI - East
La Quinta Inn & Suites by Wyndham Madison American Center

La Quinta Inn & Suites by Wyndham Madison American Center

3 out of 5
5217 E Terrace Dr Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $107 per night from Jul 9 to Jul 10
CA $107
CA $123 total
Jul 9 - Jul 10
includes taxes & fees
8.2/10 Very good! (1,422 reviews)
"Very friendly staff and clean room. My flight was delayed so I appreciated the flexibility with late check in as well."

Reviewed on Jul 2, 2026

La Quinta Inn & Suites by Wyndham Madison American Center
See all 377 properties in Waterloo
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

Stay near popular Waterloo attractions

Holzhueter Farm State Park

6.0/10 (1 review)
You can take time to visit Holzhueter Farm State Park during your travels to Waterloo.
See properties

Frequently asked questions

How much does a Waterloo vacation package cost?
You can pick up a vacation package to this top destination from CA $1,123 on Expedia. However, how much your vacation to Waterloo costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Waterloo?
January, February and November are the best times to search for cheap Waterloo vacation packages. Opting to travel in less busy periods means you can usually find reduced prices on flights and hotels.
How many days is enough for Waterloo?
The ideal length for your Waterloo vacation depends on what you'd like to do. Generally, a few days to a week will give you plenty of time to go to all the major sights and explore some hidden gems along the way.
How to find the best Waterloo package deals?
Finding a cheap Waterloo package deal is a cinch with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget range, apply a couple of filters and see what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most economical Waterloo package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Waterloo vacation as a package?
You can enjoy significant savings on your next Waterloo getaway by booking a personalized vacation package. Check the "Package" heading, then select your travel dates and destination to view the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Waterloo?
Score incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Waterloo trip.
How to plan a trip to Waterloo?

  1. Pick the ideal time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to visit Waterloo.
  2. Budget wisely: Besides the cost of your hotel, you'll need to factor in other expenses too. These include food, flights and transportation. Also, put aside some extra funds for unexpected costs that could crop up during your trip to Waterloo.
  3. Determine how many days away: Start by listing all the attractions you'd like to experience in Waterloo. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a customized Waterloo vacation package.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.