Riley Vacations from $489

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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.
Days Inn & Suites by Wyndham Madison

Days Inn & Suites by Wyndham Madison

2 out of 5
Price was $548, price is now $489 per person
$489
per person
Apr 22 - Apr 26
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Madison (MSN)
8.4/10 Very Good! (1,003 reviews)
The room was clean. The staff was both courteous and helpful providing a couple of things we forgot.

Reviewed on Feb 22, 2026

Christmas Mountain Campground

Christmas Mountain Campground

3 out of 5
Price was $752, price is now $580 per person
$580
per person
Apr 2 - Apr 6
found 11 hours ago
Roundtrip flight included
New York (NYC) to Madison (MSN)
9/10 Wonderful! (77 reviews)
Great staff. Room has plenty of useful essentials that you not have thought about brining.

Reviewed on Feb 23, 2026

Best Western Plus InnTowner Madison

Best Western Plus InnTowner Madison

3 out of 5
Regent
Price was $742, price is now $622 per person
$622
per person
Apr 22 - Apr 26
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Madison (MSN)
9.2/10 Wonderful! (1,005 reviews)
Shuttle to the hospital was so very helpful

Reviewed on Feb 19, 2026

1810 Emerson House Bed & Breakfast - Adults Only

1810 Emerson House Bed & Breakfast - Adults Only

3.5 out of 5
Price was $874, price is now $751 per person
$751
per person
Apr 9 - Apr 12
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Madison (MSN)
9.6/10 Exceptional! (11 reviews)
The hosts were gracious and thorough with amenities. The property was lovely and comfortable. The food was delicious.

Reviewed on Jul 11, 2024

The Speckled Hen Inn B&B

The Speckled Hen Inn B&B

4 out of 5
Price was $724, price is now $636 per person
$636
per person
Apr 17 - Apr 19
found 1 day ago
Roundtrip flight included
New York (NYC) to Madison (MSN)
9.8/10 Exceptional! (9 reviews)
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The Annual Vacation Sale

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Discover the most popular places to visit in Riley

Man sampling craft beer at a restaurant

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

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

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

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
$139 nightly
The price is $161 total per night from Mar 15 to Mar 16
$161 total
Mar 15 - Mar 16
Total with taxes and fees
9.4/10 Exceptional! (3,510 reviews)
Always happy with our stay here! We love the area around the capitol when visiting our

Reviewed on Feb 26, 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
$60 nightly
The price is $69 total per night from Mar 11 to Mar 12
$69 total
Mar 11 - Mar 12
Total with taxes and fees
8/10 Very Good! (1,182 reviews)
Staff was most helpful and room was excellent

Reviewed on Feb 25, 2026

Baymont by Wyndham Madison West/Middleton WI West
Moxy Madison Downtown

Moxy Madison Downtown

3.5 out of 5
823 East Washington Ave Madison WI
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $134 total per night from Mar 8 to Mar 9
$134 total
Mar 8 - Mar 9
Total with taxes and fees
9.2/10 Wonderful! (409 reviews)
Super cool hotel, great staff - welcoming, friendly and helpful. The welcome glass of champagne was a nice surprise. Rooms are a not your typical hotel room, but artsy, warm, inviting. Only complaint was that the record player didn’t work. I believe the issue might have been a dead battery in the ...

Reviewed on Feb 26, 2026

Moxy Madison Downtown
See all 339 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.

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 $489 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.