Madison Holiday Rentals

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Holiday Rentals in Madison

Our top choices for Madison holiday rentals

Kasa South Side Pittsburgh

4.0 star property
8.2 out of 10, Very good, (95)
"Clean great views hotel "
The price is AU$266
includes taxes & fees
19 Oct - 20 Oct
Kasa South Side Pittsburgh

Home away from home!!!

8.8 out of 10, Excellent, (31)
"Great, clean, perfect location"
The price is AU$983
includes taxes & fees
22 Sept - 23 Sept
Home away from home!!!

Peaceful 3-Bedroom Country Farmhouse Situated on 125 Acre Horse Farm

10.0 out of 10, Exceptional, (8)
"Great time host was awesome "
Peaceful 3-Bedroom Country Farmhouse Situated on 125 Acre Horse Farm

Shadyside Penthouse

6.8 out of 10, (13)
"Great neighborhood; very safe area and within walking distance of shops/stores. Bedrooms were extremely spacious with comfortable mattresses and bedding/pillows in good condition. The large table in the main living area was great for seating a large group for meals and our family game night! Home is sparsely furnished and could use some nicer window coverings and some additional seating in living area. Towels provided were a bit worn and surprised it did not have a full size coffee pot. Owner...
Shadyside Penthouse

Enjoy Urban Living at our Steel City Getaway w/ Seasonal Hot Tub!

9.8 out of 10, Exceptional, (43)
"The house and location was perfect for our girlfriend get away. Location was convenient to museums and attractions. Owner was easy to work with. Would definitely stay here again. "
Enjoy Urban Living at our Steel City Getaway w/ Seasonal Hot Tub!

Charming 3-bedroom house in Delmont with WiFi and AC

9.6 out of 10, Exceptional, (4)
"We were there for USOpen. Nice, easy place with great communication with host "
The price is AU$417
includes taxes & fees
4 Oct - 5 Oct
Charming 3-bedroom house in Delmont with WiFi and AC

❤️Cozy Townhome on Carey with Private Deck Space ❤️

8.4 out of 10, Very good, (28)
"got a lil warm in the house the first night but over all a great place"
The price is AU$375
includes taxes & fees
1 Oct - 2 Oct
❤️Cozy Townhome on Carey with Private Deck Space ❤️

Easy access, roomy, close to so much but in a private country setting.

10.0 out of 10, Exceptional, (60)
"This was the third time we have stayed at Chet's place. The location works well for us and the place is roomy and clean."
Easy access, roomy, close to so much but in a private country setting.

Retro 70s! Near MM103 of Gap Trail!

10.0 out of 10, Exceptional, (1)
"Clean. Definitely 70’s vibe. "
The price is AU$347
includes taxes & fees
24 Sept - 25 Sept
Retro 70s! Near MM103 of Gap Trail!

Close to all things in Pittsburgh

6.0 out of 10, (4)
"Beautiful home has classic details with modern conveniences. House and neighborhood were both top notch. Would definitely stay here again when I come back to the area. Very easy and quick drive to downtown. "
The price is AU$301
includes taxes & fees
28 Sept - 29 Sept
Close to all things in Pittsburgh

Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!

7.0 out of 10, Good, (6)
"Tom was very communicative during the whole stay and had great recommendations! We loved the place, well situated on the South side for easy walking along Carson. Wonderful time in Pittsburgh! "
The price is AU$375
includes taxes & fees
1 Oct - 2 Oct
Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!

✰Self Check-In✰Backyard✰Decks✰Full Kitchen✰W/D✰Smart TVs✰FREE Parking✰Cozy Beds

2.0 star property
10.0 out of 10, Exceptional, (4)
"Wonderful christmas stay in a lovely cozy home! We just planned on renting a home for a night in pittsburgh for our holiday trip but we got ao much more than that! Nestled in a quiet neighborhood just outside of the busy city this place has the perfect location for being 20 minutes to all the attractions. Off street parking made unloadiing and loading a breeze. The home itself is smaller but it doesnt feel that way! Such a good use of space with a nice litlle kitchen that has all your needs!...
✰Self Check-In✰Backyard✰Decks✰Full Kitchen✰W/D✰Smart TVs✰FREE Parking✰Cozy Beds

King bed I 1 block to Carson l Game Room l Fire Pit l BBQ l Sleeps 10 l AC l

King bed I 1 block to Carson l Game Room l Fire Pit l BBQ l Sleeps 10 l AC l

Chic 1-bedroom apartment with WiFi, AC in brilliant Pittsburgh

9.6 out of 10, Exceptional, (12)
"Cutest room, loved the TV room with all the windows. Owner was super nice and the area was great. As a female staying alone, I highly recommend this place! I felt safe and comfortable! "
Chic 1-bedroom apartment with WiFi, AC in brilliant Pittsburgh

Minimalist Townhouse with Stunning Skyline View

10.0 out of 10, Exceptional, (12)
"Good for a short stay "
Minimalist Townhouse with Stunning Skyline View

💜Highland Park Hideaway - Private Deck Space and Free Parking💜

8.2 out of 10, Very good, (25)
"Host showed great communication and the property was very clean and comfortable."
The price is AU$351
includes taxes & fees
29 Sept - 30 Sept
💜Highland Park Hideaway - Private Deck Space and Free Parking💜

Charming 2-bedroom building with fitness room and AC in Clairton

The price is AU$264
includes taxes & fees
21 Sept - 22 Sept
Charming 2-bedroom building with fitness room and AC in Clairton

Hidden Gem in Swissvale sleeps 6

9.4 out of 10, Exceptional, (31)
"Stay was great."
Hidden Gem in Swissvale sleeps 6

Kasa See a Show at Kelly Strayhorn Theater The Maverick

2.0 star property
Kasa See a Show at Kelly Strayhorn Theater The Maverick

Luxury apt+Gym+ EV Parking+Near Pitt UNI UPMC

2.0 star property
8.8 out of 10, Excellent, (6)
"quiet apartment in a great location with easy access around town"
Luxury apt+Gym+ EV Parking+Near Pitt UNI UPMC
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 Madison Hotel Reviews

Find out more about Madison

Find out more about Madison

Everything you need to know about Madison 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 Madison 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 Madison holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Madison holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Madison. 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 Madison 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 Madison holiday rentals we have selected for you start as low as AU$264 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Madison rentals

At Expedia, we put the best Madison 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 Madison 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 Madison 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 Madison. 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 Madison?

Yes, there are holiday rentals close to the most popular sights in Madison, 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 Madison has to offer?

Home away from home!!!: This holiday home rental outside of Madison offers a fireplace, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

What can I see and do in Madison?

Explore the area and family-friendly sights such as Stone Villa Wine Cellars, or get out into nature at a spot like Madison Park. In the wider area, you’ll find Seton Hill University and The Palace Theatre.

What are holiday rentals like in Madison?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Madison. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for family trips.