Madison Vacation Rentals

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Vacation Rentals in Madison

Kasa South Side Pittsburgh

4.0 star property
8.6 out of 10, Excellent, (69)
"An excellent hotel for an excellent price! The hotel consists of units in an apartment building which have been purchased by the hotel company. Overall the units are very nice and spacious, with a full kitchen in unit. I stay here whenever I visit Pittsburgh!"
Kasa South Side Pittsburgh

House in the mountains with spectacular views of the Waterfront and Monogahala!

The price is CA $172
CA $370 total
includes taxes & fees
Jan 8 - Jan 9, 2025
House in the mountains with spectacular views of the Waterfront and Monogahala!

Shadyside Penthouse

7.4 out of 10, Good, (9)
"Great communication from the owner.Appreciated the fact that he allowed me to check in a little early and offered a late check out as well, Both were very helpful "
Shadyside Penthouse

❤️Cozy Townhome on Carey with Private Deck Space ❤️

8.6 out of 10, Excellent, (22)
"Property was as advertised. Clean, Great location. Had the kitchen items we needed. Plenty of room for all. Worked well for 4 of us. Beds could have been a little more comfortable on the main level. Upper level beds comfortable. Lots of stairs. But most South side flat properties will have lots of stairs. Location made up for all of that and we were satisfied. The host communicated perfectly, timely and met our needs.Clean property. Definitely worth what we paid for it. Mike"
The price is CA $79
CA $370 total
includes taxes & fees
Jan 8 - Jan 9, 2025
❤️Cozy Townhome on Carey with Private Deck Space ❤️

420 FRIENDLY /ROMANTIC GETAWAY/ GREAT HOSTING SPACE

9.8 out of 10, Exceptional, (19)
"Saw Iron Maiden and needed a place to stay. Short Uber ride from downtown. Plenty of parking. House was very clean!!"
420 FRIENDLY /ROMANTIC GETAWAY/ GREAT HOSTING SPACE

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

10.0 out of 10, Exceptional, (33)
"Very clean& spacious, plenty of room for our family of 6. Loved the outdoor space with hot tub & grill!"
Enjoy Urban Living at our Steel City Getaway w/ Hot Tub!

Reimagined 1915 Heritage House

10.0 out of 10, Exceptional, (18)
"Great property and very convenient to everyone we wanted to visit. "
Reimagined 1915 Heritage House

Pet-Friendly Apollo Home w/ Furnished Deck!

9.0 out of 10, Wonderful, (8)
"Traveling for a wedding, our family decided to be together. It was wonderful. This was a perfect home for the 10 of us. The home is very spacious w everything you need. Communication w the owner was simple and prompt. Location was peaceful & the neighborhood appeared safe. Thank you for contributing to some wonderful memories! . "
Pet-Friendly Apollo Home w/ Furnished Deck!

Spacious Cape Cod in Monroeville

7.4 out of 10, Good, (3)
"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 CA $178
CA $414 total
includes taxes & fees
Jan 8 - Jan 9, 2025
Spacious Cape Cod in Monroeville

Pet-Friendly Home - 100 Feet to Walnut Street

10.0 out of 10, Exceptional, (25)
"We had a lovely stay. When staying with dogs it is good to note that there is no grass in the yard or close by to take them out easily. The gate on the back yard fence does not latch so you can’t let dogs loose in the yard safely to play. Otherwise the apartment is exactly how it is described."
Pet-Friendly Home - 100 Feet to Walnut Street

Stay at The Forge Loft in historic Homstead Pennsylvania!

9.4 out of 10, Exceptional, (11)
"This place provided a great place for family to come and visit us while we were in town. The area has some great restaurants within walking distance and shopping a short car ride away. When booking I knew there were stairs but had no idea how steep they would be to get into the apartment. I was worried my elderly parents wouldn’t be able to navigate but we made it without any issue. It was a cute place and had ample space for our whole family. It is in a busy street so be aware you will hear...
Stay at The Forge Loft in historic Homstead Pennsylvania!

Home away from home!!!

8.2 out of 10, Very good, (20)
"Overall well. I wish the unit was a little cleaner. The property is beautiful so a little more TLC would have been good. The downstairs area needed cleaned. The bathroom floor wasn’t clean. The toilet wasn’t clean but I cleaned everything to my liking upon checking in and it made our stay better. We felt safe and enjoyed to fireplace lights."
The price is CA $538
CA $911 total
includes taxes & fees
Dec 30 - Dec 31
Home away from home!!!

Hydee's Hideaway

10.0 out of 10, Exceptional, (12)
"Good stay"
The price is CA $215
CA $552 total
includes taxes & fees
Jan 8 - Jan 9, 2025
Hydee's Hideaway

15 minutes from Downtown, PNC Park, 5 minutes from Monroeville

2.0 out of 10, (5)
"This property looks like a condemned house! Was dirty! No blankets on the beds. Bathroom was unfinished and had no shower curtain. Been trying to get refund from them and getting no responses!! Need to take off Expedia site!! "
The price is CA $172
CA $243 total
includes taxes & fees
Jan 8 - Jan 9, 2025
15 minutes from Downtown, PNC Park, 5 minutes from Monroeville

Beautiful, High-End, A/C, All New 2BR/1BA

9.0 out of 10, Wonderful, (8)
"We enjoyed our stay here. Pros: Whoever set up the apartment did a fantastic job. It was absolutely beautiful. There were great amenities (iron, monitor, etc). It felt very spacious and the location was great. There was parking, heating, and very hot water in the shower. Wifi was also great. There was also a washer and dryer. The host was very kind and responsive. He answered all our calls. Cons: Whoever is cleaning/upkeeping the apartment is not doing a fantastic job. The keypad had died so...
Beautiful, High-End, A/C, All New 2BR/1BA

Comfortable and clean whole apartment, great for couples and friends getaways.

9.6 out of 10, Exceptional, (13)
"Excellent property! Lots of attention to detail shows pride of ownership. It has everything you need and is much better than a hotel room. We went to Carnegie Music hall which is only 10 minutes away. Super convenient. Street parking in a quiet neighborhood. Great restaurant choices within 15 minutes. Will stay here in the future."
Comfortable and clean whole apartment, great for couples and friends getaways.

Bettis Plant/ Kennywood Cape Cod

9.0 out of 10, Wonderful, (6)
"Clean, host responded promptly to questions"
Bettis Plant/ Kennywood Cape Cod

⁂ Cozy Nook off Carson - Free Parking & Private Entry ⁂

9.4 out of 10, Exceptional, (8)
"Very nice apartment and the location is great. Walking distance to everything in the Southside strip. "
⁂ Cozy Nook off Carson - Free Parking & Private Entry ⁂

Skyline Views & Adventure ★ Dogs 👍 ★ Professionally Cleaned ★ Close to all!

9.8 out of 10, Exceptional, (6)
"prime location! however this is the slopes, so parking is limited. clean, pet-friendly space. comfy beds!"
Skyline Views & Adventure ★ Dogs 👍 ★ Professionally Cleaned ★ Close to all!

Family-Friendly Townhome: 16 Mi to Pittsburgh!

10.0 out of 10, Exceptional, (16)
"This rental is in a very nice quiet community with enough green space for us to easily walk our dogs. The townhouse is just as pictured. Very clean. Comfy beds and enough towels for all. Just enough in the kitchen for fixing a quick meal if you didn't go out. We were easily able to travel up to Allison Park or into Squirrel Hill for dinner. We definitely would rent again."
Family-Friendly Townhome: 16 Mi to Pittsburgh!
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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Other types of properties in Madison you may be interested in

Hampton Inn Pittsburgh/Monroeville

2.5 star property
8.2 out of 10, Very good, (1003)
"Very good "
The price is CA $145
CA $166 total
includes taxes & fees
Jan 21 - Jan 22, 2025
Hampton Inn Pittsburgh/Monroeville

The Maverick by Kasa

3.0 star property
8.8 out of 10, Excellent, (523)
"Absolutely our favorite place to stay in the Burgh! Great location and the concierge service is outstanding "
The price is CA $89
CA $102 total
includes taxes & fees
Jan 2 - Jan 3, 2025
The Maverick by Kasa

Hampton Inn Pittsburgh University/Medical Center

2.5 star property
8.0 out of 10, Very good, (1002)
"Great location. Close to campus and restaurants."
The price is CA $157
CA $179 total
includes taxes & fees
Jan 2 - Jan 3, 2025
Hampton Inn Pittsburgh University/Medical Center
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.

Frequently asked questions

Are there vacation rentals in Madison?

Yes, you can find vacation rentals close to well known attractions in Madison, or you can go with a more remote option if you're looking for relaxation.

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

❤️Cozy Townhome on Carey with Private Deck Space ❤️: This vacation home near Madison is located in the city center 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 you can cook with friends or family.

What can I see and do in Madison?

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

What are vacation rentals like in Madison?

Vacation rentals are privately owned accommodations you can stay in for a couple days or more in Madison. Vacation rentals offer 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 vacation rental can provide a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you to travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for family gatherings.