Holiday Rentals in Madison

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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, (89)
"Surprised at the room cleanliness. This is our 4th time staying at this property. And the no parking was a little disappointing."
Kasa South Side Pittsburgh

❤️Cozy Townhome on Carey with Private Deck Space ❤️

8.6 out of 10, Excellent, (26)
"got a lil warm in the house the first night but over all a great place"
The price is €216
includes taxes & fees
1 Sept - 2 Sept
❤️Cozy Townhome on Carey with Private Deck Space ❤️

Home away from home!!!

8.8 out of 10, Excellent, (31)
"Great, clean, perfect location"
The price is €569
includes taxes & fees
24 Aug - 25 Aug
Home away from home!!!

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

10.0 out of 10, Exceptional, (58)
"My husband, mom and aunt stayed at Chet’s place to attend a family event in Irwin. This is the cleanest rental I’ve stayed at. It is well supplied, the internet is great and the beds are comfortable. We already have plans to stay again in a couple of months."
Easy access, roomy, close to so much but in a private country setting.

6 Mi to Dtwn: Pittsburgh Townhome w/ Porch

9.8 out of 10, Exceptional, (39)
"Every aspect of the property was very clean which is the most important thing for me. Plenty of room for three families. Convenient for our purpose; able to walk to some activities. Liked being able to easily control the temperature. Shower in downstairs bathroom was small but adequate.Street was busy but always able to find parking in the same block. "
6 Mi to Dtwn: Pittsburgh Townhome w/ Porch

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

9.6 out of 10, Exceptional, (11)
"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

JACKSON HILL CABIN

10.0 out of 10, Exceptional, (4)
"Great place, great location. Will definitely stay here again while in town."
JACKSON HILL CABIN

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

9.8 out of 10, Exceptional, (42)
"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!

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

9.4 out of 10, Exceptional, (3)
"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 €215
includes taxes & fees
25 Aug - 26 Aug
Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!

Pet-friendly home next to Oakmont & Veltre's + a few miles to Pittsburgh events!

10.0 out of 10, Exceptional, (4)
"Easy check in! Shelly was wonderful to communicate with and thorough! We had a great stay! There were even some snack she left and coffee which came in handy! Definite recommend staying there!"
The price is €270
includes taxes & fees
2 Sept - 3 Sept
Pet-friendly home next to Oakmont & Veltre's + a few miles to Pittsburgh events!

Hidden Gem in Swissvale sleeps 6

9.4 out of 10, Exceptional, (31)
"Wonderful place. Just where we needed to be. Host was very responsive with all questions!!! I will defiantly stay here again!!!"
Hidden Gem in Swissvale sleeps 6

Shadyside Penthouse

6.8 out of 10, (13)
"We were in Pittburgh for our child's graduation. While the overall physical space is as described and the location was very good, the house was undergoing some renovation and was very sparse in terms of furniture. Moreover, there were many flies in the house, missing pillow case covers, and some spaces required additional cleaning. "
Shadyside Penthouse

City Living—sleeps 12 15-20 mins from Acrisure Stadium, PNC Park, Mt Washington

2.0 star property
9.8 out of 10, Exceptional, (7)
"We had the best time in Pittsburgh! Absolutely amazing host! Would highly recommend this house to anyone! Cant wait to stay again next year! "
The price is €565
includes taxes & fees
25 Aug - 26 Aug
City Living—sleeps 12 15-20 mins from Acrisure Stadium, PNC Park, Mt Washington

Retro 70s! Near MM103 of Gap Trail!

10.0 out of 10, Exceptional, (1)
"Clean. Definitely 70’s vibe. "
The price is €195
includes taxes & fees
27 Aug - 28 Aug
Retro 70s! Near MM103 of Gap Trail!

3-bedroom townhome in delightful Pittsburgh with WiFi, AC

8.0 out of 10, Very good, (1)
"Great location for short drives to the sites in Pittsburgh. Can walk to restaurants and stores. "
The price is €282
includes taxes & fees
24 Aug - 25 Aug
3-bedroom townhome in delightful Pittsburgh with WiFi, AC

Walk to Walnut St: Pet-Friendly Pittsburgh Home!

10.0 out of 10, Exceptional, (38)
"Great place near Carnegie Mellon and in a nice neighborhood. Will definitely stay again."
Walk to Walnut St: Pet-Friendly Pittsburgh Home!

Cozy Studio with Unique Charm in Private Setting

10.0 out of 10, Exceptional, (65)
"Perfect for our visit"
The price is €159
includes taxes & fees
25 Aug - 26 Aug
Cozy Studio with Unique Charm in Private Setting

Cozy 4-bedroom house in delightful Elizabeth with AC, WiFi

Cozy 4-bedroom house in delightful Elizabeth with AC, WiFi

The Schenley Room on Beatty

7.6 out of 10, Good, (4)
"We enjoyed our stay. Excellent location close to everything we needed. Definitely we will stay here again."
The Schenley Room on Beatty

NEW Gorgeous 4bd near universities Hot tub + Games

10.0 out of 10, Exceptional, (2)
"This property was perfect for 8 adults who wanted to stay close to downtown Pittsburgh. We were there to coach a youth baseball tournament and attend a Pirates game. Close to all venues and downtown Picklesburgh celebration."
NEW Gorgeous 4bd near universities Hot tub + Games
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

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?

❤️Cozy Townhome on Carey with Private Deck Space ❤️: This holiday home rental outside of Madison is located in the city centre, and offers a patio, air conditioning and laundry facilities 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.

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.