Riley Vacations from $467

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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.
  • A modern hotel room with a flat-screen TV, a coffee machine, a dining table, a sofa, and a large window with curtains.
    Jan 21 - Jan 24

    Madison Marriott South + Flight

    Madison
    3 nights
    3.5 star property
    9.0/10 - Wonderful (622 reviews)
    "We were in town for the Wisconsin–Rutgers game, and even though the game didn’t go our way, we really enjoyed our stay at the Madison Marriott! The hotel was absolutely spotless, the staff was so friendly, and I loved the decor. Everything was modern and elegant, with beautiful neutral tones and a really understated style. One of my favorite features was the separate vanity area in the bathroom with a huge backlit mirror. Such a nice touch and perfect for doing makeup! I wish more hotels had..."
    Reviewed November 9, 2026
    Roundtrip • Cincinnati (CVG) - Madison (MSN)
    CVG - MSN • 1 stop MSN - CVG • 1 stop
    $578
    $467
    per traveler
    found 4 hours ago
    Madison Marriott South
  • A water play area with a frog slide and a water fountain.
    Jan 21 - Jan 24

    All Star Inn & Suites + Flight

    Wisconsin Dells
    3 nights
    2.0 star property
    9.2/10 - Wonderful (851 reviews)
    "Good"
    Reviewed November 10, 2026
    Roundtrip • Cincinnati (CVG) - Madison (MSN)
    CVG - MSN • 1 stop MSN - CVG • 1 stop
    $1,898
    $1,314
    per traveler
    found 4 hours ago
    All Star Inn & Suites
  • An indoor swimming pool with a wooden archway, a bar area, and a view of a waterfall.
    Jan 21 - Jan 24

    Dellshire Resort + Flight

    Wisconsin Dells
    3 nights
    3.5 star property
    9.0/10 - Wonderful (552 reviews)
    Roundtrip • Cincinnati (CVG) - Madison (MSN)
    CVG - MSN • 1 stop MSN - CVG • 1 stop
    $700
    $514
    per traveler
    found 4 hours ago
    Dellshire Resort
  • A wooden deck with chairs overlooking a body of water and a grassy area.
    Jan 21 - Jan 24

    Club Wyndham Tamarack + Flight

    Wisconsin Dells
    3 nights
    3.5 star property
    9.4/10 - Exceptional (26 reviews)
    "First stay at this property , very nice, we will be back"
    Reviewed October 31, 2026
    Roundtrip • Cincinnati (CVG) - Madison (MSN)
    CVG - MSN • 1 stop MSN - CVG • 1 stop
    $634
    $504
    per traveler
    found 4 hours ago
    Club Wyndham Tamarack
  • A waterfront hotel with outdoor seating and a view of the sunset over the water.
    Jan 21 - Jan 24

    The Edgewater + Flight

    Downtown Madison
    3 nights
    4.5 star property
    9.4/10 - Exceptional (1,000 reviews)
    Roundtrip • Cincinnati (CVG) - Madison (MSN)
    CVG - MSN • 1 stop MSN - CVG • 1 stop
    $653
    $527
    per traveler
    found 4 hours ago
    The Edgewater

Riley Hotel Deals

A modern indoor space with seating, a stone accent wall, and large windows.

AmericInn by Wyndham Madison West

AmericInn by Wyndham Madison West
3.0 star property
6.8 mi from Riley
9.0 out of 10, Wonderful, (1,411 reviews)
"You can tell the staff takes pride in their work and enjoys making the customer experience top tier. The property was clean, the breakfast was delicious with lots of options, there was a BATHTUB in the hotel room (I love a good tub soak and seems most hotels don't have tubs anymore), and we had a lovely stay. The only thing that was a bit of a bummer was free wi-fi was only available for rewards members. Overall, the price point was perfect and delivered beyond expectations. I'll be staying at...
$65 nightly
The price is $76
Dec 2 - Dec 3
Total with taxes and fees
AmericInn by Wyndham Madison West
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.
See all properties in Riley

Frequently Asked Questions

How much does a Riley vacation package cost?

You'll find cheap prices from $467 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.