Holiday houses in Shadyside

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Top-rated holiday rentals in Shadyside

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Top Guest favourite
The exterior entrance of the apartment is shown, featuring a short path lined with greenery. A wooden ramp leads up to the door, surrounded by various plants, creating a welcoming and natural entrance. The door is framed with a glass panel, allowing light to enter.
Apartment in East Liberty
4.97 out of 5 average rating, 148 reviews

Cozy One-Bedroom East Side Apartment

Spacious and comfortable one-bedroom apartment centrally located in the East End (East Side) of Pittsburgh. Cozy bedroom, full kitchen, bathroom, living room, and dining area. Quiet neighborhood; close to restaurants, supermarkets, coffee shops, bars, East Liberty Transit Center. On bus lines for easy access around town. The apartment is also located on the bus line to Pittsburgh Paints Arena and is about a 20-minute drive to PNC Park and Heinz Field. Great for couples, solo travelers, LGBTQIA.

Superhost
A living space is presented with a neutral color palette. A couch and chair are arranged around a small coffee table. A dining area with a table and four chairs is visible in the background. Natural light filters through vertical blinds on a nearby window, illuminating the space.
Apartment in Shadyside
4.78 out of 5 average rating, 689 reviews

Sunny Spacious Shadyside 1 bedroom

Bright one bedroom apartment can sleep up to three.Centrally located and just steps from Shadyside Hospital.The apartment offers guests easy access to numerous attractions, museums, stadiums, and concert venues.Just a few minutes walk to bars, restaurants, grocery stores, and shopping.This quaint apartment is perfect for a short or long term stay.Designated parking space makes it easy for you to come and go as you please.Fully equipped kitchen.Public transportation and rentable bikes close by.

Superhost
A spacious bedroom features a king-sized bed adorned with crisp white linens and a green decorative throw pillow. A study desk is positioned beside a window, allowing natural light to fill the room. Two rolled towels are neatly arranged on the bed.
Apartment in Shadyside
4.83 out of 5 average rating, 189 reviews

Spacious Double King bed Penthouse Suite

Discover the charm of our cozy 2-bedroom penthouse suite in the friendly Shadyside neighborhood. This newly renovated retreat is a short distance from all that Pittsburgh has to offer! Steps away from Pittsburgh's Favorite coffee shop - Yinz Coffee! 💫 2 King beds w/ desks in each bedroom 💫 Pet friendly 💫 24/7 Guest support 💫 Free off-street parking 💫 Close to CMU / Pitt *Please note this is a 3rd floor unit with no elevator, so be prepared to walk up 3 full flights of stairs (35 steps).

Top Guest favourite
The exterior of a sunporch suite is displayed, featuring large wall-to-wall windows framed by white columns. A pathway leads to the entrance, surrounded by lush greenery, including a bush. The home showcases a charming blend of white and red brick, adding character to the facade.
Guest suite in Highland Park
4.98 out of 5 average rating, 288 reviews

Historic Sunporch Suite

Welcome! We are delighted to share with you our favorite room in an 1895 Georgian Colonial home. This comfortable sunporch suite is ideal for two guests or a family with a young child. Located in a safe, quiet, and wonderful section of Pittsburgh, we are close to the zoo and Children's Hospital, and a short drive from downtown. This suite has its own separate entrance, bathroom, and kitchenette. The wall-to-wall windows look over the front yard, courtyard, and our neighbor's Victorian home.

Guest favourite
A cozy bedroom features a spacious bed draped in a soft, natural-toned coverlet. A vintage mirror and wooden dresser are positioned against a brick wall. Natural light filters through a stained glass window, illuminating plants nearby. A glimpse of the bathroom is visible in the background.
Apartment in Shadyside
4.9 out of 5 average rating, 10 reviews

A Home In The Heart of Shadyside

Cozy 1 bedroom home steps from Walnut St. It's a little bit rough and a little bit refined (it's our latest work in progress). Its our home and we travel a lot, so we love to share our space with others. Walker's paradise; and very bike-able, with city bikes a block away. AC and heating. * Quiet, safe, and beautiful tree-lined streets * Carnegie Mellon University and East liberty- 6 min by bicycle * University of Pittsburgh - 9 min by bicycle * Shared courtyard and front porch

Guest favourite
A bedroom features a wooden bed with a neatly arranged striped comforter. Neutral-toned artwork adorns the wall above the bed. Soft lighting from a bedside lamp provides illumination, and a doorway leads to a bright, airy space beyond.
Apartment in Shadyside
4.92 out of 5 average rating, 139 reviews

Shadyside/Pittsburgh, Modern & Stylish 1BD, w/Prkg

Stylish and family oriented modern 1 Bedroom apartment with a central location in Shadyside, located minutes to UPMC Hospitals, Universities, Walnut St. Enjoy the proximity to shopping, bars & restaurants. This apartment features 1 bedroom & Dining area and FREE Parking. Stylishly setup, our home features high speed internet and Smart Home Security system for additional safety of our guests. This place is suitable for families, executives, expats and this is NOT a party place.

Top Guest favourite
A cozy bedroom features a tufted headboard and a comfortable bed adorned with decorative pillows and a gray throw. Natural light filters through a large window with blinds, while a bedside table and stylish lamp complete the elegantly simple decor.
Apartment in Shadyside
4.86 out of 5 average rating, 161 reviews

Shadyside apartments: 1 Bed-1 full BA Jewel!

Shadyside jewel! Spacious, stylish-&- chic! Conveniently located in the prime of Pittsburgh's favorite walkable neighborhood. Extraordinary comfortable interior with in-suite laundry & exclusive covered front porch! Eat-in or dine out. There are many near-by restaurants, quaint shops, unique restaurants & bars, beautiful city parks, culture-rich museums, state-of-the-art sports facilities, Universities, Hospitals. Super easy access to public transportation too!

Guest favourite
A modern living area features a kitchenette with a small refrigerator and microwave, alongside a comfortable white chair and a sleek gray sofa. A wall-mounted TV displays a city skyline, while exposed brick adds a touch of character. Natural light filters in through a window.
Home in Friendship
4.88 out of 5 average rating, 538 reviews

PRIVATE MINI STUDIO (D2)

This Mini Studio is for anyone needing a neat, clean, cool place to stay. It has a new queen bed, sleeper sofa, a kitchenette and a full bathroom with a private entrance on the 3rd floor of a beautiful 1890s Pittsburgh mansion. It's the size of a large room and works very well with guests that are planning to work, or go out enjoying the city and come back to a safe, clean and comfy place to recharge for the night (not suitable for kids under 10).

Guest favourite
An open-concept living area features a modern kitchen with white cabinetry and granite countertops. A comfortable sofa sits in front of a coffee table, while a mounted flat-screen television displays various streaming options. Soft lighting is provided by a ceiling fan and recessed lighting.
Apartment in Shadyside
4.92 out of 5 average rating, 118 reviews

Betwn Walnut & Ellsworth! Sleeps4! Parking&Laundry

LOCATION! LOCATION! This apartment is approx 200 feet to Ellsworth Avenue and approx 700 feet to Walnut Street! My apartment features a deck, open-concept layout, central air, and free laundry. One parking spot is available for free, if reserved in advance. Please see the parking policy below. The apartment sleeps 4 people. The bedroom has a queen bed. The living room has a sofa that conveniently folds down into a queen-sized bed.

Guest favourite
Apartment in Bloomfield
4.92 out of 5 average rating, 317 reviews

Cozy Entire AptA Friendship Park & free parking

Ground Floor Entire apartment with one bedroom, living room, bathroom is located in Bloomfield, a quiet yet vibrant neighborhood that’s central to all the best attractions. It features off Street parking , a rare find in the central city. The apartment was recently updated and feels fresh, spacious. This first floor space has 1 bedroom with a queen bed, a well equipped kitchen, and a luxurious bathroom & shower.

Guest favourite
A private bedroom features a full size bed with a gray quilt and floral pillows. A purple throw blanket is draped across the bed. A desk and chair occupy one corner, illuminated by a small lamp. Soft green walls and a window with white blinds complete the space.
Private room in Greenfield
4.95 out of 5 average rating, 155 reviews

Comfy bedroom, The Run

Private bedroom for 1 person. Newly renovated 125 year old house. Former steel mill neighborhood near Pitt & CMU. Safe and plenty of free parking. Room has full size bed, desk and window fan. Room is in house with 2 other Airbnb rooms with guests. Room is upstairs, steep stairs to 2nd floor. Two full shared bathrooms. Freeway behind house will create some noise. Free parking on street, best if you have a car.

Guest favourite
The living area features a cozy sofa and a decorative fireplace, complemented by a flat-screen TV and an accent chair. Natural light enters through large windows with wooden blinds. A dining table with chairs is situated in the open space, enhancing the welcoming environment.
Apartment in Shadyside
4.87 out of 5 average rating, 15 reviews

#6 - Lovely one bedroom in the heart of Shadyside

Welcome to Shadyside STAY, your cozy home base in Pittsburgh’s most walkable neighborhood. Just steps from Walnut Street’s coffee shops and boutiques, and minutes from CMU, Pitt, and UPMC Shadyside. CMU’s free shuttle stops right outside, making campus access effortless. Perfect for students, professors, young pros, and visiting parents, our apartments blend classic Pittsburgh charm with fresh, modern vibes

Popular amenities for Shadyside holiday rentals

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Avg. price$138 NZD$140 NZD$152 NZD$169 NZD$195 NZD$200 NZD$181 NZD$195 NZD$183 NZD$180 NZD$171 NZD$156 NZD
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Quick stats about holiday rentals in Shadyside

  • Total holiday rentals

    Explore 320 holiday rentals in Shadyside

  • Nightly prices starting at

    Shadyside holiday rentals start at $52 NZD per night before taxes and fees

  • Verified guest reviews

    Over 27,330 verified reviews to help you choose

  • Family-friendly holiday rentals

    110 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 110 rentals that welcome pets

  • Rentals with dedicated workspaces

    250 properties have a dedicated workspace

  • Wi-Fi availability

    320 of Shadyside holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Shadyside rentals

  • 4.9 Average rating

    Shadyside stays are highly rated by guests—averaging 4.9 out of 5!

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