Madison Holiday Rentals

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Holiday Rentals in Madison

Property grounds
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
10.0 out of 10, Exceptional, (80)
"Clean, easy check in and quiet. As advertised."
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
Living area
Amazing townhouse, amazing attractions, amazing city!
10.0 out of 10, Exceptional, (136)
"We rented this place to visit family in Madison and attend a ren faire. It was great as we were looking for a small place with a full kitchen to cook. Neat touches with the Alexa with song and light recommendations. We enjoyed the living room white board - played lots of Pictionary. Our group was myself, my daughter, and my sister. The basement den made a great third bedroom. I might recommend a pull out couch."
Amazing townhouse, amazing attractions, amazing city!
Living area
A Pleasant Retreat- No Cleaning Fee & New Discounts
10.0 out of 10, Exceptional, (186)
"This was our first experience renting this home & we're definitely booking this home again next year. Everything from very attentive, kind renters, too extremely clean & renovated home, extremely comfortable beds & pillows. Not to mention the gorgeous & relaxing back yard. Perfect place to stay, for sure"
A Pleasant Retreat- No Cleaning Fee & New Discounts
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Dining
Near DT Madison - One Block from Lake Monona & Lake Loop Bike Path
10.0 out of 10, Exceptional, (17)
"Our stay at the Pink Acorn was amazing! Kelly truly makes her guests feel welcome. She left a sweet note and lovely treats. The house is stocked with everything you need and was exceptionally clean. The beds are super comfortable and have nice cozy blankets. Am added bonus was seeing rabbits and chipmunks in the backyard. Kelly leaves directions to walk to the beach around the corner and it’s a must do…and make sure to grab some ice cream at the shop across from the park."
Near DT Madison - One Block from Lake Monona & Lake Loop Bike Path
Smart TV
Monona Home
10.0 out of 10, Exceptional, (19)
"Great property. Fenced in back yard great for dogs!"
Monona Home
Fridge, microwave, oven, stovetop
Cozy, Spacious Downtown Verona 3 Bedroom Home
10.0 out of 10, Exceptional, (17)
"The property was clean, tidy and highly functional. 5 stars!"
Cozy, Spacious Downtown Verona 3 Bedroom Home
Outdoor dining
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
10.0 out of 10, Exceptional, (18)
"Everything about our stay was fantastic! The house was nicely decorated and extremely clean. The kitchen was well appointed and had everything we needed. Beds were comfy. Shower was great. A perfect place for our group of friends to spend a long weekend. I wouldn’t hesitate to stay here again!"
The price is NZ$859
per night
18 Jun - 19 Jun
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Interior
Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path
10.0 out of 10, Exceptional, (13)
"We loved our visit to Madison, made even more special with our stay in this awesome retro house! All of the special touches throughout the house were amazing, we would definitely stay here again in the future."
Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path
Interior
Conveniently Located just off University Avenue on Madison's West Side
10.0 out of 10, Exceptional, (105)
"Had a great time enjoyed the place very much."
Conveniently Located just off University Avenue on Madison's West Side
Living area
Large Home close to everything, Dogs welcome.
10.0 out of 10, Exceptional, (1)
"We were in town visiting sick family and unfortunately spent most of our time at the hospital. The home was located within 15 mins of UW Hospital and many local restaurants and shopping. The home had plenty of bedrooms and space if traveling with a larger group. We did take our dog and though there isn’t much yard space the neighborhood is great for a walk. Very safe and quiet. The only negative to the house would be the stairs if anyone has mobility issues. You have to do stairs to get to...
Large Home close to everything, Dogs welcome.
Property grounds
Perfect For Large Groups And Families ~ 7.1 Miles From UW Madison
10.0 out of 10, Exceptional, (69)
"We had a great time in Madison, and was so glad we found this home. Plenty of room to spread out, it had everything we needed. We really enjoyed the pool and hot tub. Highly recommend this home"
Perfect For Large Groups And Families ~ 7.1 Miles From UW Madison
Outdoor dining
‘Happy’s Haven’ Cabin w/ Gas Grill & Fire Pit!
10.0 out of 10, Exceptional, (36)
"We had a great time! House was so clean and stocked with everything we needed. Would definitely stay again. Just adorable! I would recommend cutting the grass and storing your wood in a sheltered area. The wood was too wet to use-we had to purchase some & the grass was long with prickly vines on the stairs. The grass was long around the BBQ."
‘Happy’s Haven’ Cabin w/ Gas Grill & Fire Pit!
Property grounds
Cozy cottage retreat that’s perfect for recharging.
10.0 out of 10, Exceptional, (35)
"Stayed with 3 other adult friends. Location was secluded, quiet and definitely felt cabin-y. The huge yard was perfect for lawn games and sitting by the fire. We enjoyed how many places there were to sit, inside and out. Sleeping arrangements were great and the cabin was very well suited for hosting guests. Little things like sunscreen that we had forgotten were a nice touch. The river was a little off color. Some of our group swam but I wouldn’t book the place with intentions of being in the...
Cozy cottage retreat that’s perfect for recharging.
Fridge, microwave, oven, stovetop
Legacy Guest House , Mount Horeb WI
10.0 out of 10, Exceptional, (36)
"Nice place to stay"
Legacy Guest House , Mount Horeb WI
Outdoor dining
Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard
10.0 out of 10, Exceptional, (132)
"We loved our stay. The house was comfortable and clean. It had all the amenities. The location was spectacular, and the backyard was super peaceful. Joan was a great host and communication was easy. There are three bedrooms for six people and a full-size futon, which is great for our group of 6."
Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard
Lake
Newly updated water retreat. PONTOON for rent, FREE golf & ICE at local course
10.0 out of 10, Exceptional, (21)
"We absolutely enjoyed our stay. Great location, clean, and had everything we needed. Would stay there again. Excellent communication and customer service! Thank you!"
Newly updated water retreat. PONTOON for rent, FREE golf & ICE at local course
Madison & ~UW~-Madison Area Lakefront Home
9.8 out of 10, Exceptional, (165)
"The cottage is clean and well stocked for a long weekend. The view of the lake is beautiful, and I'm sure it's even better in the warm months. We had everything we needed. Great little house for a long weekend."
Madison & ~UW~-Madison Area Lakefront Home
Fridge, microwave, oven, stovetop
Doty ★ Walk to Everything -Hotel Quality- Downtown
9.8 out of 10, Exceptional, (21)
"My many family members stayed at the property and gave only positive feedback. The large open living room/kitchen was perfect for all activities. They accessed many things by walking or driving at times. I worried that the daytime moving of parked cars on the street was an inconvenience, but three young men in the group didn't seem to mind. Parking ramps were easily available to others who visited."
Doty ★ Walk to Everything -Hotel Quality- Downtown
Fridge, microwave, oven, stovetop
10min to Capitol - Trails & Parks - East Madison
9.8 out of 10, Exceptional, (14)
"Great little getaway. Cute place in a nice area and close to many popular places in Madison."
The price is NZ$681
per night
28 May - 29 May
10min to Capitol - Trails & Parks - East Madison
Property grounds
Enjoy Nature with Full Comfort!
9.8 out of 10, Exceptional, (9)
"I enjoyed this location. Was the perfect size for one person (or a couple’s getaway). The room was secure and safe. Clean and had some nice little extras in the room. Marca was very attentive to all communication we had. The scenery out the big bay window was lovely as well. Would stay again if the opportunity arose."
The price is NZ$211
per night
28 May - 29 May
Enjoy Nature with Full Comfort!
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See all available properties in Madison
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.

Other types of properties in Madison you may be interested in

Exterior
The Madison Concourse Hotel and Governor's Club
3.5 star property
9.4 out of 10, Exceptional, (1612)
"Convenient. Quality. Quiet. Secure."
The price is NZ$245
per night
23 May - 24 May
The Madison Concourse Hotel and Governor's Club
Reception
DoubleTree by Hilton Madison East
4.0 star property
9.4 out of 10, Exceptional, (617)
"Very Clean and well taken care of property. Have stayed here many times and will return when ever in Madison. "
The price is NZ$256
per night
3 Jun - 4 Jun
DoubleTree by Hilton Madison East
Exterior
Best Western Plus InnTowner Madison
3.0 star property
9.0 out of 10, Wonderful, (1000)
"Friendly staff and very clean room. Seems recently remodeled."
The price is NZ$284
per night
27 May - 28 May
Best Western Plus InnTowner Madison
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Madison holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Madison. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Madison. Seeing all the best attractions is bound to make you fall in love with Madison. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Madison short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Madison?

Yes, there are holiday rentals in Madison close to Henry Vilas Zoo, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the university campus and scenic lakeside in Madison. The array of shops and entertainment choices are some other things you might want to check out while you're here.

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

A Pleasant Retreat- No Cleaning Fee & New Discounts: This highly rated holiday home rental in Madison offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Some other top choices in Madison are Hot Tub, with a View, Private Modern Garden Level Apartment, Conservancy Access and NEW OWNER SPECIAL>Madison Lakefront Home.

How many holiday rentals are there in Madison?

Expedia has 90 holiday rentals for your stay in Madison.

What’s there to see and do in Madison?

Henry Vilas Zoo and Madison Children's Museum are a couple of the family-friendly sights, whereas cultural attractions include Orpheum Theater and Overture Center for the Arts. While here, State Street Shopping and Wisconsin State Capitol are other places worth a visit.

What’s a holiday rental in Madison like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Madison. Holiday rentals offer amenities like WiFi and washers and dryers so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a family trip.

Recent reviews of Madison properties
Expedia verified reviews