Riley Vacation Packages

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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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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.
Courtyard by Marriott Madison East

Courtyard by Marriott Madison East

3 out of 5
Price was CA $1,404, price is now CA $1,253 per person
CA $1,253
per person
Sep 10 - Sep 15
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Madison (MSN)
9/10 Wonderful! (681 reviews)
Great Staff, Clean Room...Everyone was super helpful. The only thing is there is no shuttle to the airport, I specifically thought there was one since I booked it based on this criteria. Bummer but we just ubered. Would stay here again.

Reviewed on Jul 15, 2026

Graduate by Hilton Madison

Graduate by Hilton Madison

4 out of 5
Downtown Madison
Price was CA $2,367, price is now CA $1,976 per person
CA $1,976
per person
Sep 10 - Sep 15
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Madison (MSN)
9/10 Wonderful! (1,002 reviews)

Hilton Garden Inn Madison West/Middleton

Hilton Garden Inn Madison West/Middleton

3 out of 5
Price was CA $1,510, price is now CA $1,311 per person
CA $1,311
per person
Sep 10 - Sep 15
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Madison (MSN)
8.8/10 Excellent! (1,001 reviews)
The only thing bad was. The fan on AC only worked on low. The freezer on the refrigerator was caked with frost. Other than that it was a very nice place. We didn’t eat breakfast because it cost much extra.

Reviewed on Jul 12, 2026

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 $2,678, price is now CA $2,378 per person
CA $2,378
per person
Sep 10 - Sep 15
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Madison (MSN)
9.4/10 Exceptional! (4,007 reviews)
We loved our stay here. Very nice room, very clean and fantastic location in front of the capitol building. Will definitely stay here again when visiting Madison!!!

Reviewed on Jul 16, 2026

Fairfield Inn & Suites by Marriott Madison East

Fairfield Inn & Suites by Marriott Madison East

3 out of 5
Price was CA $1,453, price is now CA $1,292 per person
CA $1,292
per person
Sep 10 - Sep 15
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Madison (MSN)
9.2/10 Wonderful! (1,004 reviews)

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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
The price is CA $198 per night from Aug 9 to Aug 10
CA $198
CA $229 total
Aug 9 - Aug 10
includes taxes & fees
9.4/10 Exceptional! (3,982 reviews)
"We loved our stay here. Very nice room, very clean and fantastic location in front of the capitol building. Will definitely stay here again when visiting Madison!!!"

Reviewed on Jul 16, 2026

The Madison Concourse Hotel and Governor's Club
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 $99 per night from Aug 4 to Aug 5
CA $99
CA $114 total
Aug 4 - Aug 5
includes taxes & fees
8/10 Very good! (1,360 reviews)
"This is about a 1.5-star hotel with a 5-star shower. The hotel staff are very nice and helpful. And the room was fine. The hotel is quite large, and I can say that I got in a lot of steps walking from the front desk to my room, which was at the back of the building. So if you don't want to walk so ..."

Reviewed on Jul 16, 2026

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

Best Western Plus InnTowner Madison

3 out of 5
2424 University Avenue Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $227 per night from Jul 25 to Jul 26
CA $227
CA $263 total
Jul 25 - Jul 26
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
"Great location near us hospital clean pool and hot tub Excellent continental breakfast options"

Reviewed on Jul 16, 2026

Best Western Plus InnTowner Madison
See all 346 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.
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What to do in Riley

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 Riley

Frequently asked questions

How much does a Riley vacation package cost?
You'll find cheap prices from CA $1,253 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.

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.