Riley Vacations from $187

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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!

The Latest Riley vacation packages

Price found within the past 48 hours. Click for updated prices.
Motel 6 Janesville, WI

Motel 6 Janesville, WI

2 out of 5
Price was $242, price is now $187 per person
$187
per person
Dec 27 - Dec 31
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Madison (MSN)
14/10 Exceptional! (827 reviews)
The rooms were good

Reviewed on Nov 23, 2025

Madison Marriott South

Madison Marriott South

3.5 out of 5
Price was $609, price is now $441 per person
$441
per person
Jan 13 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Madison (MSN)
18/10 Exceptional! (524 reviews)
Great location along the lake and trails

Reviewed on Aug 10, 2025

Hilton Madison Monona Terrace

Hilton Madison Monona Terrace

4 out of 5
Downtown Madison
Price was $508, price is now $378 per person
$378
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Madison (MSN)
17.2/10 Exceptional! (1,004 reviews)
Check-in was nice and easy. Bar had a wide variety of cocktails and friendly staff. Breakfast was amazing at Audrey‘s.

Reviewed on Nov 22, 2025

Christmas Mountain Campground

Christmas Mountain Campground

3 out of 5
Price was $715, price is now $540 per person
$540
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Madison (MSN)
18/10 Exceptional! (77 reviews)
Very clean facilities. Very clean cabins. Top notch !

Reviewed on Nov 9, 2025

Fairfield by Marriott Inn & Suites Madison South

Fairfield by Marriott Inn & Suites Madison South

2.5 out of 5
Price was $478, price is now $363 per person
$363
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Madison (MSN)
18.4/10 Exceptional! (102 reviews)
Pool was great. The Manager was the Best, she was very empathetic whilevwe going through the worst trauma - my 35 year old hasvLate Stage Progressive Pulmonary Fibrosis with only 1-2 years to live unless she gets a double lung transplant, daughter going through extremely rigorous, long, exhausting evaluations, tests, meetings, to see if she can even get on the Stephanie Gerndt’s Help Hope Live Campaign Page is live! {https://helphopelive.org/campaign/26376/} YOU CAN Help Save Her Life with our GREATEST OF GREAT GRATITUDES! Please Donate, can be bits at a time over time. Spread word to your Churches, other Organizations, Families, Friebfs, etc. I will have Fliers and Business Carfs as well to distribute. Feel free to post messages to Dear Stephie on here as well.

Reviewed on Nov 21, 2025

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Discover the most popular places to visit in Riley

Verona Ice Arena

Enjoy a trip to Verona Ice Arena and popular activities like biking in Verona. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.

Verona Ice Arena

Reddan Soccer Park

Enjoy a trip to Reddan Soccer Park and popular activities like biking in Verona. Stroll along the lakeside or attend a sporting event in this family-friendly area.

Reddan Soccer Park

Wisconsin Brewing Company

Enjoy a trip to Wisconsin Brewing Company and popular activities like biking in Verona. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.

Wisconsin Brewing Company

What to do in Riley

Haunted Madison Capitol Building on Madison Ghosts Haunted Walking Tour

Murmurs of Mourning & Murder: Madison Ghost Tour

$32
per adult
Murmurs of Mourning & Murder: Madison Ghost Tour
Trolley Pub Public Tour

Trolley Pub Public Tour

$45
per adult
Trolley Pub Public Tour
See all activities in Riley

Find the Best Riley Vacation Packages

Riley Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Dane County Regional Airport (MSN)
Top Sights
Wisconsin Brewing Company, Firemans Beach and Reddan Soccer Park

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Frequently asked questions

How much does a Riley vacation package cost?
You'll find cheap prices from $187 on Expedia for your Riley escape. However, 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?
You're likely to find reduced prices and better availability in November, December and January. Explore our cheap Riley vacation packages and you could get some excellent off-season deals.
How many days is enough for Riley?
Usually, a handful of days is enough to tick off the major sights during your Riley vacation. However, if you'd like to have some time to unwind or take day trips, think about extending your itinerary.
How to find the best Riley package deals?
Bagging a cheap Riley package deal is a cinch with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, add some filters and see what's available. You can personalize your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to view the most economical Riley package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are typically lower.
Is it cheaper to book a Riley vacation as a package?
You can enjoy significant savings on your next Riley retreat by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to see the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Riley?
Enjoy amazing discounts by reserving your flights early with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for an impromptu Riley getaway.
Does Expedia offer Book Now, Pay Later Riley vacation packages?
Set off on your dream escape to Riley with our Book Now, Pay Later vacations. There's no need to save up or wait for your next paycheck — we've teamed up with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans let you split the cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to budget for your trip and snap up cheap deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.