Riley Holiday Rentals

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Our top choices for Riley holiday rentals

Aparthotel in Tenney-Lapham

The Dylin by Mint House
4.0 star property
9.4 out of 10, Exceptional, (121)
"Great stay at the Dylin"
United States
Lauri
The price is AU$192
includes taxes & fees
23 Dec - 24 Dec
The Dylin by Mint House
10.0 out of 10, Exceptional, (131)
"It was great!"
United States
Guitar string S.
Conveniently Located just off University Avenue on Madison's West Side
10.0 out of 10, Exceptional, (147)
"This is a unique home that is super clean and had everything needed to cook, entertain (we played games & watched football) and accommodate any family. The location was close to downtown, the interstate, and airport. Plenty of restaurants were nearby as well. We thoroughly enjoyed our stay and would absolutely stay again. "
United States
Connie C.
ONE OF A KIND vacation rental with a view
9.8 out of 10, Exceptional, (7)
"Perfect spot for a family getaway"
United States
Steve M.
Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!
9.6 out of 10, Exceptional, (69)
"Beautiful location, nice spacious and clean spot. We had a great time. "
United States
Sarah B.
Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail
10.0 out of 10, Exceptional, (119)
"Scenic property, super zen, lovely hosts!"
United States
Christina C.
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
The price is AU$246
includes taxes & fees
21 Dec - 22 Dec
Pool with Slide. Great for Business Travelers!
9.8 out of 10, Exceptional, (36)
"Beautiful apartment with all we needed for a comfortable family July 4th weekend away!! "
United States
Mindi Z.
The price is AU$441
includes taxes & fees
15 Dec - 16 Dec
Doty ★ Walk to Everything -Hotel Quality- Downtown
9.6 out of 10, Exceptional, (22)
"Barn was beautiful, clean & fun amenities."
United States
Kerry S.
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
10.0 out of 10, Exceptional, (12)
"Nice stay"
United States
Rebecca S.
Charming 4 Bed, 2.5 Bath home minutes from Madison perfect for any occasion.
10.0 out of 10, Exceptional, (202)
"What a lovely place to spend a few days with family! There was so much to do within a short distance but we loved being able to just chill on the water. We had a wonderful stay and can’t wait to visit again. Would highly recommend! "
United States
Jody G.
Madison & ~UW~-Madison Area Lakefront Home
10.0 out of 10, Exceptional, (2)
"We had a fantastic stay at this property, and it truly exceeded our expectations. The location is excellent—perfectly situated with convenient access to both the east and west sides of Madison, making it easy to get wherever we needed to go. The owners were incredibly helpful and responsive, answering the few questions we had quickly and kindly, which made the entire experience even smoother.One of the biggest highlights for us was the private fenced-in area, which was absolutely perfect for our...
United States
Jessi P.
The price is AU$461
includes taxes & fees
4 Jan - 5 Jan 2026
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
10.0 out of 10, Exceptional, (19)
"Very clean and comfortable and a great location within walking distance to downtown."
United States
Holly
The price is AU$313
includes taxes & fees
16 Dec - 17 Dec
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
10.0 out of 10, Exceptional, (52)
"Great stay - very relaxing!"
United States
Karen S.
On the Yahara River, access to Madison Lakes
9.8 out of 10, Exceptional, (47)
"We had a great time on our weekend trip to Madison. Location was super quick to get to downtown, house was clean, and we really enjoyed taking the canoe out on the lakes to explore."
United States
Molly S.
The price is AU$757
includes taxes & fees
16 Dec - 17 Dec
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
10.0 out of 10, Exceptional, (30)
"good location and value for the money. We were pleased to bring our dog with us!"
United States
audrey w.
Clean and spacioius flat in great location near Epic and downtown Verona!

Holiday Home in Verona

Paoli Den - Renovated Flat!
9.8 out of 10, Exceptional, (31)
"Charming place, great communication with owners!"
United States
Ed D.
Paoli Den - Renovated Flat!
8.0 out of 10, Very good, (5)
"Great place for a stay."
United States
Andy D.
The price is AU$225
includes taxes & fees
14 Dec - 15 Dec
King Suite | Free Breakfast. Pool and Hot Tub

Holiday Home in Cross Plains

Cozy Cabin in The Driftless
9.2 out of 10, Wonderful, (63)
"The cabin was clean and well supplied. It was great for our long weekend getaway"
United States
rose b.
Cozy Cabin in The Driftless

Holiday Home in Mount Horeb

Luxurious Country Retreat
9.8 out of 10, Exceptional, (16)
"Overall, we thoroughly enjoyed our stay. Property is large and has many wonderful features for hosting many other guests. Host was very prompt with communication responses, which we greatly appreciated. Would definitely stay again! "
United States
Amanda R.
Luxurious Country Retreat
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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Top Riley Hotel Reviews

Find out more about Riley

Everything you need to know about Riley holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Riley holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Riley holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Riley holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Riley. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Riley holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Riley holiday rentals we have selected for you start as low as AU$192 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Riley rentals

At Expedia, we put the best Riley holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Riley rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Riley holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Riley. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Riley?

Yes, there are holiday rentals close to the most popular sights in Riley, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Riley has to offer?

Conveniently Located just off University Avenue on Madison's West Side : This holiday home rental outside of Riley offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

What can I see and do in Riley?

Explore the area and family-friendly sights such as Verona Ice Arena, or get out into nature at a spot like Cave of The Mounds National Natural Landmark. In the wider area, you’ll find University Ridge Golf Course and Mt. Horeb Area Museum.

What are holiday rentals like in Riley?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Riley. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for a small group gathering.