Riley 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*

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    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

Your Riley Vacation

With everything organized before you go, our Riley vacation packages mean you can concentrate on having fun. Whether you base yourself in the neighborhood of Shorewood Hills, which is good for golfing, or another part of town, this lively city offers plenty of discoveries. Love to explore your surroundings? University Ridge Golf Course, Reddan Soccer Park and Verona Ice Arena are three of the top places to visit during a trip to Riley. Stop daydreaming and start traveling. Browse the many options on Expedia today and put your Riley vacation plans into motion!

Top Riley Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Best Western Premier Park Hotel

Best Western Premier Park Hotel

4 out of 5
Downtown Madison
Price was CA $1,490, price is now CA $1,429 per person
CA $1,429
per person
Nov 30 - Dec 3
found 24 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Madison (MSN)
9.6/10 Exceptional! (1,006 reviews)
Awesome staff! Definitely cleaned room and very very nice place to stay

Reviewed on Oct 30, 2026

The Edgewater

The Edgewater

4.5 out of 5
Downtown Madison
Price was CA $1,717, price is now CA $1,641 per person
CA $1,641
per person
Nov 30 - Dec 3
found 24 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Madison (MSN)
9.4/10 Exceptional! (1,008 reviews)

Hilton Madison Monona Terrace

Hilton Madison Monona Terrace

4 out of 5
Downtown Madison
Price was CA $1,496, price is now CA $1,446 per person
CA $1,446
per person
Nov 30 - Dec 3
found 24 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Madison (MSN)
8.6/10 Excellent! (1,003 reviews)
Great stay

Reviewed on Oct 28, 2026

Hyatt Place Madison / Verona

Hyatt Place Madison / Verona

3 out of 5
Price was CA $1,547, price is now CA $1,501 per person
CA $1,501
per person
Nov 30 - Dec 3
found 24 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Madison (MSN)
9.4/10 Exceptional! (1,003 reviews)

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
Downtown Madison
Price was CA $1,472, price is now CA $1,432 per person
CA $1,432
per person
Nov 30 - Dec 3
found 24 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Madison (MSN)
9.4/10 Exceptional! (4,264 reviews)

Ready to book your vacation to Riley?

 

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Riley 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 $165 per night from Nov 8 to Nov 9
CA $165
CA $191 total
Nov 8 - Nov 9
includes taxes & fees
The Madison Concourse Hotel and Governor's Club
Motel 6 Madison, WI - East

Motel 6 Madison, WI - East

2 out of 5
4202 E Towne Blvd Madison WI
Fully refundable
The price is CA $62 per night from Nov 10 to Nov 11
CA $62
CA $71 total
Nov 10 - Nov 11
includes taxes & fees
6.2/10 (1,059 reviews)
"They sold my room after I had booked it with Expedia and had my confirmation number. And when I called the staff was very rude and disrespectful"

Reviewed on Oct 28, 2026

Motel 6 Madison, WI - East
AmericInn by Wyndham Madison West

AmericInn by Wyndham Madison West

3 out of 5
516 Grand Canyon Dr Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $96 per night from Nov 8 to Nov 9
CA $96
CA $111 total
Nov 8 - Nov 9
includes taxes & fees
AmericInn by Wyndham Madison West
See all 375 properties in Riley
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
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Family Vacations
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What to do in Riley

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
See all activities in Riley

Frequently asked questions

How much does a Riley vacation package cost?
You'll find cheap prices from CA $1,429 on Expedia for your Riley escape. However, a range of factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Riley costs.
What are the cheapest months to go to Riley?
If you're hoping to score a cheap Riley vacation package, consider travelling in January, February and November. You're likely to find better rates on hotels and flights during these quieter months — ideal for budget-conscious travellers.
How many days is enough for Riley?
When planning your Riley vacation, a handful of days will be enough to see the top spots. Be sure to stop by Goodman Aquatic Centre — it's one of the main attractions in this destination. If you're after more activities, think about basing yourself here and setting off on some tours from Riley.
How to find the best Riley package deals?
Bagging a cheap Riley package deal is a breeze with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, add a few filters and see what's available. You can tweak your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most affordable Riley package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Riley vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll usually snag a better deal than booking each component separately. And you'll still enjoy the flexibility to create a customized Riley vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Riley?
If you've got your Riley travel dates confirmed, book as early as you can to score some incredible deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Riley?

  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to go to Riley.
  2. Plan your budget wisely: As well as the price of your hotel, you'll need to consider other expenses too. These include flights, food and transportation. Also, set aside a little extra for unexpected costs that may arise during your trip to Riley.
  3. Decide how long to go for: Now that you know more about Riley, you can work out the right length of your break. Create a draft plan and allocate enough time to cover everything you want to do.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to choose a Riley vacation package that brings all your bookings together.

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