Riley Holiday Rentals

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Holiday Rentals in Riley

The Dylin

4.0 star property
9.2 out of 10, Wonderful, (78)
"Very comfortable and convenient. Would be happy to stay there again."
The Dylin

Relax in this clean cozy 3 bedroom, 2 bath home in the heart of Madison. Perfect

2.0 out of 10, (2)
"Host never showed up to let us in the property and still has not reimbursed me "
Relax in this clean cozy 3 bedroom, 2 bath home in the heart of Madison. Perfect

Charming 2-bed apartment with WiFi, AC in brilliant Madison

The price is AU$276
includes taxes & fees
8 Aug - 9 Aug
Charming 2-bed apartment with WiFi, AC in brilliant Madison

Two bedroom suite with city views in the heart of downtown Madison

9.8 out of 10, Exceptional, (29)
"Perfect for a weekend in Madison. A good location close to everything. "
The price is AU$709
includes taxes & fees
27 July - 28 July
Two bedroom suite with city views in the heart of downtown Madison

One Bedroom King with Den with views of Lake Monona in the heart of downtown.

9.4 out of 10, Exceptional, (22)
"The property was beautiful, safe, and in a perfect location for the event we were attending!"
The price is AU$608
includes taxes & fees
27 July - 28 July
One Bedroom King with Den with views of Lake Monona in the heart of downtown.

One Bedroom King with Den with views of the heart of downtown.

2.0 star property
9.6 out of 10, Exceptional, (20)
"Great stay, easy location."
The price is AU$587
includes taxes & fees
27 July - 28 July
One Bedroom King with Den with views of the heart of downtown.

Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail

9.6 out of 10, Exceptional, (61)
"The property was beautiful and our group of 8 had tons of space. It was beautiful and we wish we could’ve stayed longer. We would definitely stay there again. "
Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail

Doty ★ Walk to Everything -Hotel Quality- Downtown

9.8 out of 10, Exceptional, (33)
"Had a great stay!"
Doty ★ Walk to Everything -Hotel Quality- Downtown

Studio queen with views of Lake Monona in the heart of downtown Madison

9.4 out of 10, Exceptional, (8)
"The property location is great, walking distance to great restaurants, the Farmers market, and close to walking/running trails. "
The price is AU$466
includes taxes & fees
27 July - 28 July
Studio queen with views of Lake Monona in the heart of downtown Madison

One-of-a-kind house on 240 acres w/ prairie, woods & trout-stream - pet-friendly

10.0 out of 10, Exceptional, (49)
"A beautiful cabin, on a wonderful property, in a great part of the Driftless—not sure what more you could ask for... Highly recommended!"
One-of-a-kind house on 240 acres w/ prairie, woods & trout-stream - pet-friendly

The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

10.0 out of 10, Exceptional, (12)
"My girlfriend and I stayed at this property and we are so grateful we found it. At first we didn’t know if we were going to find anywhere available due to all the hotels/motels being booked in the surrounding area of Madison. This place had a great rate and looked really cute so we chose to book it, and I am so glad we did. Pam was really quick on communicating back to us, the check in process was seamless and the space is decorated in such a unique style. They even had some candy and other...
The price is AU$288
includes taxes & fees
3 Aug - 4 Aug
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

ONE OF A KIND vacation rental with a view

10.0 out of 10, Exceptional, (139)
"This is our second stay and will gladly come back. It is easy to maneuver around Madison and the house is a spectacular vintage 80’s home. "
ONE OF A KIND vacation rental with a view

Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!

9.6 out of 10, Exceptional, (4)
"Lots of beds and endless amenities to keep our large group busy and having fun all weekend. Would definitely stay here again. "
Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!

Conveniently Located just off University Avenue on Madison's West Side

10.0 out of 10, Exceptional, (124)
"Very spacious, well appointed house in a quiet neighborhood, convenient to Madison."
Conveniently Located just off University Avenue on Madison's West Side

Enjoy Nature with Full Comfort!

9.6 out of 10, Exceptional, (28)
"Great location, beautiful, clean, and friendly host"
The price is AU$197
includes taxes & fees
27 July - 28 July
Enjoy Nature with Full Comfort!

One Bedroom King with views of the heart of downtown.

2.0 star property
10.0 out of 10, Exceptional, (2)
"I loved the location and the area it was located. I really loved the view and the clearness of the place as well. It was very homey and cozy. "
The price is AU$548
includes taxes & fees
30 July - 31 July
One Bedroom King with views of the heart of downtown.

Two Bedroom with views of Lake Monona in the heart of downtown Madison

10.0 out of 10, Exceptional, (5)
"We loved everything about this property. Would definitely stay there again."
The price is AU$750
includes taxes & fees
27 July - 28 July
Two Bedroom with views of Lake Monona in the heart of downtown Madison

Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access

10.0 out of 10, Exceptional, (115)
"I was visiting from Chicago for a concert and was immediately sold with this property! I loved the hot tub and fireplace!! The whole house was clean and very bright! I will definitely stay again!"
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access

Paoli Den - Newly Remodeled!

9.8 out of 10, Exceptional, (21)
"We were in town for a wedding, and this was the perfect place for us and our two young children. The space was very clean and had everything we needed for our stay. The host was extremely friendly and helpful and was quick to respond to any messages. We would definitely recommend! "
Paoli Den - Newly Remodeled!

Spacious & Modern Home w/ Deck in Oregon!

7.0 out of 10, Good, (2)
"Awesome...very clean property.Plenty of space for eight people...Quiet neighborhood"
Spacious & Modern Home w/ Deck in Oregon!
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

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?

Relax in this clean cozy 3 bedroom, 2 bath home in the heart of Madison. Perfect: This holiday home rental outside of Riley is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a stovetop and a microwave.

What can I see and do in Riley?

Explore the area and family-friendly sights such as Henry Vilas Zoo, 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 Reddan Soccer Park.

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.