Madison Vacation Rentals

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Our top choices for Madison vacation rentals

Secluded Chalet near Ohiopyle and Seven Springs

Secluded Chalet near Ohiopyle and Seven Springs
Bear Rocks
10.0 out of 10, Exceptional, (3 reviews)
"Mike was great. Place is as advertised. Worked well for our weekend at Seven Springs. "
United States
Ryan C.
The price is CA $174
CA $352 total
includes taxes & fees
May 27 - May 28
Secluded Chalet near Ohiopyle and Seven Springs

3-bd home in Mt.Pleasant; child/pet friendly; festivals, biking, skiing nearby.

3-bd home in Mt.Pleasant; child/pet friendly; festivals, biking, skiing nearby.
Mount Pleasant
10.0 out of 10, Exceptional, (7 reviews)
The price is CA $155
CA $306 total
includes taxes & fees
May 25 - May 26
3-bd home in Mt.Pleasant; child/pet friendly; festivals, biking, skiing nearby.

Vintage Vogue: Your Stylish Suite with Wi-Fi, Netflix, and Parking!

Vintage Vogue: Your Stylish Suite with Wi-Fi, Netflix, and Parking!
Connellsville
10.0 out of 10, Exceptional, (9 reviews)
"We had a very comfortable cozy stay."
United States
Beth F.
The price is CA $144
CA $252 total
includes taxes & fees
May 27 - May 28
Vintage Vogue: Your Stylish Suite with Wi-Fi, Netflix, and Parking!

Yough Trail Retreat on the Great Allegheny Passage

Yough Trail Retreat on the Great Allegheny Passage
Connellsville
10.0 out of 10, Exceptional, (16 reviews)
"We highly recommend this super clean and spacious apartment! It is larger than the photos show, and as comfortable as home. Our hosts were extremely accommodating when we needed to reschedule due to illness. Very conveniently located, yet quiet and peaceful. We will definitely be back!"
United States
Amy M.
The price is CA $186
CA $338 total
includes taxes & fees
May 26 - May 27
Yough Trail Retreat on the Great Allegheny Passage

Penn Hills Home ~ 11 Mi to Pittsburgh

Penn Hills Home ~ 11 Mi to Pittsburgh
3.0 star property
Penn Hills
The price is CA $142
CA $492 total
includes taxes & fees
May 25 - May 26
Penn Hills Home ~ 11 Mi to Pittsburgh

Cabin 3 - Everything you need in this Cabin for a great weekend.

Cabin 3 - Everything you need in this Cabin for a great weekend.
Connellsville
Cabin 3 - Everything you need in this Cabin for a great weekend.

Walk to BTV Winery | Near Corporate Offices

Walk to BTV Winery | Near Corporate Offices
Hunker
10.0 out of 10, Exceptional, (11 reviews)
"Everything was wonderful - very clean, very cozy! We enjoyed our stay very much!"
United States
Kate R.
The price is CA $159
CA $436 total
includes taxes & fees
Jun 16 - Jun 17
Walk to BTV Winery | Near Corporate Offices

The Upper Room

The Upper Room
McKeesport
9.6 out of 10, Exceptional, (7 reviews)
"Great place and an awesome host!"
United States
John B.
The price is CA $144
CA $275 total
includes taxes & fees
May 26 - May 27
The Upper Room

Charming 3-bedroom house in soothing West Newton neighborhood

Charming 3-bedroom house in soothing West Newton neighborhood
West Newton
10.0 out of 10, Exceptional, (3 reviews)
"Clean and well stocked. Plenty of room in each bedroom. Location to bike trail and local eateries is a plus."
United States
Jim M.
The price is CA $210
CA $369 total
includes taxes & fees
May 25 - May 26
Charming 3-bedroom house in soothing West Newton neighborhood

Charming 3-bedroom townhome with AC and WiFi in Greensburg

Charming 3-bedroom townhome with AC and WiFi in Greensburg
Greensburg
8.8 out of 10, Excellent, (8 reviews)
"Great place to stay. Centrally located"
United States
Randall M.
The price is CA $275
CA $472 total
includes taxes & fees
May 29 - May 30
Charming 3-bedroom townhome with AC and WiFi in Greensburg

Lloyd House | 5 Kings | Sleeps 12 | Point Breeze

Lloyd House | 5 Kings | Sleeps 12 | Point Breeze
Point Breeze
The price is CA $137
CA $602 total
includes taxes & fees
May 26 - May 27
Lloyd House | 5 Kings | Sleeps 12 | Point Breeze

The Light Room

The Light Room
McKeesport
9.6 out of 10, Exceptional, (9 reviews)
"Everything was great!!"
United States
Jason B.
The price is CA $144
CA $275 total
includes taxes & fees
May 26 - May 27
The Light Room

Cozy Studio with Unique Charm in Private Setting

Cozy Studio with Unique Charm in Private Setting
South Park
10.0 out of 10, Exceptional, (79 reviews)
"What a wonderful and cozy hideaway. We absolutely loved it. The host had all the amenities you could ask for. "
United States
Laurie K.
The price is CA $186
CA $294 total
includes taxes & fees
May 25 - May 26
Cozy Studio with Unique Charm in Private Setting

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

Pet-friendly home next to Oakmont & Veltre's + a few miles to Pittsburgh events!
Plum
10.0 out of 10, Exceptional, (25 reviews)
"Our stay was great, and the place was just as described. Would stay again in the future!"
United States
Amanda W.
The price is CA $234
CA $407 total
includes taxes & fees
May 26 - May 27
Pet-friendly home next to Oakmont & Veltre's + a few miles to Pittsburgh events!

Cozy King Bed Suite ~ Free Parking & Ground Floor!

Cozy King Bed Suite ~ Free Parking & Ground Floor!
East Liberty
The price is CA $152
CA $234 total
includes taxes & fees
May 25 - May 26
Cozy King Bed Suite ~ Free Parking & Ground Floor!

Cozy Private Studio w/ Kitchenette

Cozy Private Studio w/ Kitchenette
Pittsburgh
The price is CA $121
CA $322 total
includes taxes & fees
Jun 2 - Jun 3
Cozy Private Studio w/ Kitchenette

Stylish House near Frick Park

Stylish House near Frick Park
Squirrel Hill South
9.8 out of 10, Exceptional, (9 reviews)
"Cozy house, had everything we needed in a very convenient location."
United States
Warren S.
The price is CA $155
CA $326 total
includes taxes & fees
May 26 - May 27
Stylish House near Frick Park

①min->Walnutst:CMU:Pitt

①min->Walnutst:CMU:Pitt
Shadyside
The price is CA $93
CA $297 total
includes taxes & fees
Jun 3 - Jun 4
①min->Walnutst:CMU:Pitt

Historic 3 Bed Home - Unique Experience

Historic 3 Bed Home - Unique Experience
Homestead
7.0 out of 10, Good, (8 reviews)
"Me and my friends enjoyed this space so much . The host was very kind and responsive. Definitely will book again when we come back to Pittsburgh! "
United States
Alexandria S.
The price is CA $183
CA $363 total
includes taxes & fees
Jun 13 - Jun 14
Historic 3 Bed Home - Unique Experience

M&J - 2615 Jane · Colorful Southside gem! Off-street parking!

M&J - 2615 Jane · Colorful Southside gem! Off-street parking!
South Side Flats
10.0 out of 10, Exceptional, (1 review)
"Was very nice and perfect for what we needed. Very closr to the GAP trail! "
United States
Hockey M.
The price is CA $118
CA $293 total
includes taxes & fees
May 26 - May 27
M&J - 2615 Jane · Colorful Southside gem! Off-street parking!
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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?

The Light Room: This vacation home rental near Madison is equipped with a patio, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities like a stovetop and a microwave can make your vacation run smoothly.

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.