Vacation rentals in Shadyside

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Quick stats about vacation rentals in Shadyside

  • Total vacation rentals

    Explore 410 vacation rentals in Shadyside

  • Nightly prices starting at

    Shadyside vacation rentals start at G$6,274 GYD per night before taxes and fees

  • Verified guest reviews

    Over 34,010 verified reviews to help you choose

  • Family-friendly vacation rentals

    150 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 140 rentals that welcome pets

  • Rentals with dedicated workspaces

    310 properties have a dedicated workspace

  • Wi-Fi availability

    400 of Shadyside vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Shadyside rentals

  • 4.8 Average rating

    Shadyside stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated vacation rentals in Shadyside

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A historic red brick house features a welcoming porch adorned with greenery. A colorful pride flag hangs prominently, while the well-maintained steps lead up to the entrance. Lush hedges frame the path, providing an inviting approach to the home.
Private room in East Liberty
4.96 out of 5 average rating, 116 reviews

Friendship Victorian Gold Bedroom & Private Bath

Tony and I welcome you into our Friendship neighborhood home. This room is on the 2nd floor with a queen bed and private bath. It is filled with charm. You have full use of the house including the kitchen, front and back porches and both parlors. Our house originally build by a coal and lumber baron at the turn of the past century. The house features stunning original woodwork and patterned hardwood floors. It is in the highly walk-able Friendship neighborhood, minutes from Shadyside, East Liberty, CMU, Pitt, Bakery Square and the University hospitals. Guests have access to the whole house. Join us for a glass of wine in the evening or coffee or tea in the morning. My partner, Tony and I call this home but we love guests and meeting new people. That said, we always are respectful of ones privacy. We love Friendship. It is a neighborhood filled with Victorian homes. It is know for it's massive front porches and stunning interiors. It is conveniently located in Pittsburgh's booming East end. It is within walking distance of Walnut Street and Ellsworth Avenue in Shadyside, Shadyside Hospital, the East Liberty Business District, Wholefoods, Bakery Square. It's minutes to Oakland, Children's Hospital, Bloomfield, and the Pittsburgh Zoo. http://friendship-pgh.org/ Close to public transportation and highly walkable to Google/Bakery Square, Walnut Street and Ellsworth Aveune and East Liberty. Bring your bikes or use the Bike Share: http://pghbikeshare.org/

An open concept kitchen and dining area features light hardwood flooring and white brick walls. A round wooden dining table is set with plates and utensils, surrounded by four light-colored chairs. Two bar stools are positioned at a kitchen counter in the background, alongside modern appliances.
Townhouse in Bloomfield
4.87 out of 5 average rating, 268 reviews

HOT TUB KING bed Luxurious 2 bed in PRIME location

Enjoy a stylish experience at this centrally-located getaway. I believe in maximum comfort. All the comforts and amenities of home and more; including memory foam beds, smart tv, nespresso machine, and more. *5 miles from Heinz Field *20 minute walk to Lawrenceville strip *10 minute walk to Children's Hospital *1 mile from Shadyside *5 minute walk to West Penn Hospital This is the ultimate spot for a couples retreat or extended stay... NO PARTIES ALLOWED:) Please note the open stair case!

Top guest favorite
The floating home is presented from an aerial view, showcasing its unique two-level structure nestled on the calm waters of the Allegheny River. The wrap-around deck and patio doors are visible, enhancing the connection to nature, with lush greenery lining the riverbank.
Houseboat in Blawnox
4.99 out of 5 average rating, 95 reviews

Allegheny River Aqua Villa

Experience a unique getaway on the Allegheny River with our exceptional tiny home built on a barge! This floating haven offers a distinctive reverse floor plan with luxury & breath-taking views! Lower Level- Two inviting bedrooms, each with twin beds that can convert into a king for your comfort - Full bathroom with Dual Rainfall Shower Heads. Upper Level - Open Concept Living with TV & Internet, Fully Equipped Kitchen & Peninsula. See-through gas fireplace! Patio Doors & Wrap around Decks!

Top guest favorite
Apartment in Shadyside
5 out of 5 average rating, 13 reviews

Shadyside 2 BR | Walk to Walnut + On site parking

Bright, energizing and charming 2 BDRM Shadyside apartment in Pittsburgh's most walkable neighborhood. Steps from Walnut Street's best restaurants, cafés, and boutique shops. New furniture & furnishings (work/study, too), bed 'n bath, lighting, fully equipped kitchen (even an air fryer), fast Wi-Fi, 65" TV, in-unit washer/dryer & more. Smart self-check-in, with rare off-street reserved parking (for 1 Car; also: buses nearby). Minutes to Downtown, CMU, and Pitt — your perfect in-city stay.

Top guest favorite
Home in Shadyside
5 out of 5 average rating, 30 reviews

Shadyside Home - Walk to Walnut St - Free Parking

Beautifully maintained Shadyside row home one block from Walnut Street - and no cleaning fee. Bright, open living spaces, updated appliances, lots of natural light, yet quiet inside. Walk to boutiques, cafes, and restaurants; minutes to CMU, Pitt, and UPMC - ideal for campus visits, hospital stays, or weekend trips. Two off-street parking spots, a covered front porch, and a private deck. Finished basement adds a 90" TV plus flexible space for an office, playroom, or cozy movie room.

Guest favorite
The living room features a light blue, three-seater couch positioned centrally. Nearby wooden tables flank the sofa, complimented by large windows draped with teal curtains. A round mirror and wall clock add functional decor, while subtle natural light fills the inviting space.
Apartment in Shadyside
4.89 out of 5 average rating, 232 reviews

Stunning 2 BR King Bed Suite ~ Steps from Walnut

Stunning & upscale 2 BR/ 1 bathroom perfectly located in the heart of Shadyside where you can easily walk to plenty of bars, restaurants, shops and more! ⭐️2 beds (1 King/ 1 Queen; High end memory foam mattresses) ⭐️Sleeper sofa (Queen) ⭐️Pet Friendly ⭐️Free washer/ dryer (Basement) ⭐️Fully stocked & equipped kitchen ⭐️Private back porch My team & I are here for you 24/7 before, during and after your stay with us! Message us if you have any questions or feel free to instant book!

Guest favorite
A modern bedroom is characterized by sloped wooden ceilings and exposed beams. A spacious bed with a light gray coverlet is centered against the wall, flanked by two bedside tables with lamps. Natural light enters through a small window, illuminating the wooden floor.
Apartment in Shadyside
4.86 out of 5 average rating, 273 reviews

Shadyside/Pittsburgh, Modern & Unique 1BD w/Prkng

Unique 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.

Superhost
A modern living space is equipped with a comfortable sectional sofa and a glass coffee table. The room features tasteful decor, including wall art and a circular mirror. A ceiling fan provides airflow, and an open doorway leads to the kitchen, highlighting the space's layout.
Apartment in Shadyside
4.91 out of 5 average rating, 204 reviews

Shadyside 2Bed 2Bath w/ Parking!

2 OFF STREET PARKING SPACES INCLUDED FOR FREE! In the heart of Shadyside! 1 Block to Walnut St Short Walk to UPMC & West Penn hospitals, CMU & Pitt! 2BR/2 bath apartment in a prime location, restaurants, shops, coffee shops, and fitness studios close by. The building was gutted and remodeled, everything down to the soundproofing and top of the line appliances are brand new! Free laundry included inside the unit. Fully stocked for both long and short term stays!

Guest favorite
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
4.85 out of 5 average rating, 181 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 favorite
A light-filled studio features a kitchen area with wooden cabinets and appliances, including a microwave and refrigerator. A compact dining space is situated next to a bed with soft bedding. Additional elements include a fan and a rug on the hardwood floor.
Apartment in Shadyside
5 out of 5 average rating, 27 reviews

Cozy Studio in Shadyside - Walk to CMU

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 professionals and visiting parents, this bright, fully furnished studio blends modern comfort with a welcoming vibe, the ideal spot to work, study, and relax.

Top guest favorite
A cozy bedroom features a spacious bed dressed in an orange quilt. Two windows allow natural light to fill the room, and a colorful chair sits beside a small nightstand. A decorative fireplace adds character, complemented by framed artwork hanging above.
Guest suite in Bloomfield
4.98 out of 5 average rating, 226 reviews

Sunny Friendship "Treehouse" 2 story / 1BD gem

Friendship Treehouse: Walking distance to 3 hospitals, our private, 2 story apartment w/ separate entry is steps away from great restaurants, coffee shops, yoga studios, art galleries & major bus lines. Located on a quiet tree-lined street in the aptly named Friendship area, we are an easy commute to Pitt & CMU. Our apartment is perfect for all of your travel & work needs. Suited for solo travelers, couples, and business travelers.

Top guest favorite
The living room features a light-colored pull-out couch, a marble-top coffee table, and a large 65-inch smart TV mounted on the wall. Two decorative wall art pieces are displayed alongside a closet with louvered doors. Natural light enters through a window covered by sheer curtains.
Apartment in Shadyside
4.98 out of 5 average rating, 45 reviews

①min->Walnut:CMU:UPMC

I've hosted & co-hosted for 4 years. All questions are answered here so you can make an informed decision. ★ 3 min Walk to Walnut Street ★ 3 minutes Drive to UPMC Shadyside ★ 5 min Drive to CMU ★ 5 minutes Drive to Bakery Square ★ 6 minutes Drive to University of Pittsburgh ★ 8 min drive to Duquesne University ★ 10 min drive to Downtown ★ 15 min drive to Mount Washington We take absolute pleasure in welcoming you in our home.

Popular amenities for Shadyside vacation rentals

  1. Airbnb
  2. United States
  3. Pennsylvania
  4. Allegheny County
  5. Pittsburgh
  6. Shadyside