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Top Holiday Rentals in Madison

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 £186
includes taxes & fees
11 Aug - 12 Aug
❤️Cozy Townhome on Carey with Private Deck Space ❤️

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 £186
includes taxes & fees
11 Aug - 12 Aug
Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!

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

9.6 out of 10, Exceptional, (9)
"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

6 Mi to Dtwn: Pittsburgh Townhome w/ Porch

9.8 out of 10, Exceptional, (37)
"The stay was wonderful."
6 Mi to Dtwn: Pittsburgh Townhome w/ Porch

Home away from home!!!

8.8 out of 10, Excellent, (30)
"Great, clean, perfect location"
The price is £380
includes taxes & fees
11 Aug - 12 Aug
Home away from home!!!

Charming 3-bedroom townhome with AC and WiFi in Greensburg

9.4 out of 10, Exceptional, (6)
"Great place to stay. Centrally located"
The price is £262
includes taxes & fees
11 Aug - 12 Aug
Charming 3-bedroom townhome with AC and WiFi in Greensburg

Hidden Gem in Swissvale sleeps 6

9.4 out of 10, Exceptional, (29)
"The host was excellent in communication. The property is close to the city with easy access to the Parkway. Large kitchen for those who have a longer stay and wish to have meals in. All and all comfortable and cozy."
Hidden Gem in Swissvale sleeps 6

3-bedroom house and game room in Pittsburgh with WiFi, AC

8.0 out of 10, Very good, (4)
"We really enjoyed our stay in PA! The home was comfortable and great for our family. It was a good location for exploring the city. The host communicated well and made everything easy. We'd definitely recommend it to other families! Thank you!"
The price is £187
includes taxes & fees
31 Aug - 1 Sept
3-bedroom house and game room in Pittsburgh with WiFi, AC

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 £487
includes taxes & fees
11 Aug - 12 Aug
City Living—sleeps 12 15-20 mins from Acrisure Stadium, PNC Park, Mt Washington

JACKSON HILL CABIN

10.0 out of 10, Exceptional, (2)
"Great place, great location. Will definitely stay here again while in town."
JACKSON HILL CABIN

Gorgeous Southside Slopes home with outdoor hot tub and city view!

10.0 out of 10, Exceptional, (54)
"It was the perfect location for the bachelorette party. The house was clean and comfortable. Would definitely recommend! "
Gorgeous Southside Slopes home with outdoor hot tub and city view!

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 £265
includes taxes & fees
3 Sept - 4 Sept
Close to all things in Pittsburgh

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 £233
includes taxes & fees
19 Aug - 20 Aug
Pet-friendly home next to Oakmont & Veltre's + a few miles to Pittsburgh events!

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 £536
includes taxes & fees
11 Aug - 12 Aug
3-bedroom townhome in delightful Pittsburgh with WiFi, AC

Historic 3 Bed Apartment - Unique Experience

8.0 out of 10, Very good, (9)
"My family and I absolutely loved staying here. It’s quiet, you cannot hear the neighbors. It’s an absolute adorable little place. If my family and I ever go back to Pennsylvania, we will definitely try to stay here again! "
The price is £142
includes taxes & fees
22 Aug - 23 Aug
Historic 3 Bed Apartment - Unique Experience

Retro 70s! Near MM103 of Gap Trail!

10.0 out of 10, Exceptional, (1)
"Clean. Definitely 70’s vibe. "
The price is £169
includes taxes & fees
12 Aug - 13 Aug
Retro 70s! Near MM103 of Gap Trail!

Hydee's Hideaway

10.0 out of 10, Exceptional, (21)
"Great place for a quick trip for a Steelers game. Beds were comfortable and everything was very clean and well kept. "
The price is £278
includes taxes & fees
11 Aug - 12 Aug
Hydee's Hideaway

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

Cozy 1BR/1BA + Gym Near UPMC & Carnegie Mellon

8.0 out of 10, Very good, (2)
"The place itself is great! They provide many amenities in the house- the bed is very comfortable and everything was clean. Very close to everything!!The check in process is more tedious that I have seen at other VRBOs in terms of providing identification- guests identification- but not a deal breaker.Would definitely stay again!"
Cozy 1BR/1BA + Gym Near UPMC & Carnegie Mellon
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.