
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 ﺩ.ﺇ 110 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.

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/

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!

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!

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.

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.

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!

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.

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!

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!

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.

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.

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
Stay near Shadyside's top sights
Other great vacation rentals in Shadyside

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Shadyside/Central @5 Stylish&Bright Studio w/Prkg

Spacious Double King bed Penthouse Suite

Cozy King Suite|Central, Workspace + Free Parking

Cozy King Suite with Parking!

Huge King Suite Just off Walnut

Shadyside King Suite w/ Parking!
Destinations to explore
- Pet-friendly rentals Shadyside
- Rentals with an EV charger Shadyside
- Fitness-friendly rentals Shadyside
- Apartment rentals Shadyside
- House rentals Shadyside
- Family-friendly rentals Shadyside
- Rentals with a fire pit Shadyside
- Rentals with outdoor seating Shadyside
- Rentals with a patio Shadyside
- Rentals with a fireplace Shadyside
- Rentals with a washer and dryer Shadyside
- PNC Park
- Acrisure Stadium
- Carnegie Mellon University
- Fallingwater
- Seven Springs Mountain Resort
- University Of Pittsburgh
- David Lawrence Convention Center
- Pittsburgh Zoo & PPG Aquarium
- Ohiopyle State Park
- Idlewild & SoakZone
- Sri Venkateswara Temple
- Raccoon Creek State Park
- Moraine State Park
- Point State Park
- Stage AE
- Petersen Events Center
- Phipps Conservatory and Botanical Gardens
- Kennywood
- Schenley Park
- National Aviary
- Carnegie Science Center
- Children's Museum of Pittsburgh
- PPG Paints Arena
- Senator John Heinz History Center





