
Holiday rentals in Shadyside
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Top-rated holiday rentals in Shadyside
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

Shadyside/Central @1 Spacious & Modern 1Bdr w/Prkg
Spacious 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, living room & 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.

Avant-Garde Escape by Walnut
Welcome to our stylish, newly-renovated home, complete with modern amenities, tasteful decor, and all-new everything. Perfectly located just steps from Walnut Street’s best restaurants, bars, and shops—a prime base for exploring Pittsburgh! ⭐ 2 King beds + 2 Queen beds + 5 rollaway beds or futons - can sleep 16 easily! ⭐ Private deck ⭐ Free Washer/Dryer ⭐ 2 Off-Street Parking spaces (Free) ⭐ Pack N Play & High Chair Our team is here 24/7 to support you before, during, and after your stay!

Queen Bed Suite|Heart of Shadyside|Walkable &Quiet
Stylish and freshly renovated 1 BR/ 1 bath apartment perfectly located in the heart of Shadyside where you can easily walk to plenty of bars, restaurants, shops and more! Fully equipped for an extended stay, weekend getaway, or just a place to crash for the night. ⭐️Super comfy queen memory foam mattress 🌟24/7 Guest support ⭐️Free off-street parking! 🌟Fully stocked & equipped kitchen ⭐️Queen sized pull out sofa 🌟Pet Friendly (Must provide vaccination records) ⭐️Laundry (Free and in-unit)

Premium King Bed | Free Park & Gym | UPMC/CMU/Pitt
✨ Welcome to our stylish and modern apartment in the heart of Shadyside! This fully furnished 1 bedroom suite features sleek décor, a fully equipped kitchen, cozy living space and luxurious king bed. Enjoy top-tier amenities, including: 🔹 Fitness Center & Yoga Studio 🔹 Free Street Parking 🔹 Complimentary Coffee Station 🔹 Variety of Co-Working Spaces 🔹 Resident Clubroom with TV 🔹 Courtyard with BBQ & Ping Pong Table 🔹 EV Charging Station 🔹 On-Site Retail 🔹 Bike Storage Room

Highly Walkable | <10 Min to Shadyside Favs!
✨Bold, modern, & unmistakably Pittsburgh!✨ Our 3br/2ba home spans the 2nd & 3rd floors, wrapped in sleek black-and-gold style with plush furnishings, premium finishes, and smart home tech. Perfect for friends or couples, you’ll enjoy a fully stocked kitchen, lightning-fast Wi-Fi, and a coffee bar that rivals your favorite café. Just steps to Shadyside, East Liberty, & Bakery Square bars, restaurants, and coffee shops, too! With Chore-Free Checkout® so you can focus on fun, not chores.

Chic Shadyside Apt w/ Balcony-1Block to Walnut St!
In the heart of Shadyside! 1 Block to Walnut St Short Walk to UPMC & West Penn hospitals, CMU & Pitt! 1BR/1 bath apartment with private covered balcony w/ TV in a prime location, dozens of restaurants, shops, coffee shops, and fitness studios close by. The building was gutted and entirely 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!

East End Penthouse in Shadyside w/rooftop deck
Modern and full of art, color, and light. A private spot to be inspired, reflect, write and or daydream.This luxury and unique 2 bedrooms, 3-level apartment is above a family home in the Shadyside/East End area. It is on a quiet residential street w/ ample outdoor space to conference and work from home. It has its own stunning private rooftop space,open floor plan, a true oasis in the city! Walkable to many local coffee/bars, gyms, shops and eateries in East Shadyside.

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!

PRIVATE FULL STUDIO IN PITTSBURGH (C2)
This Studio is for anyone needing a neat, clean, cool place to stay. It has a new queen bed, a new sleeper sofa, a full kitchen and a full bathroom with a private entrance on the 2rd 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).

StudioApt W/Gym+eV+Free Parking+Near Pitt Uni UPMC
Welcome to our stunning cozy 1-bed studio unit. Perfect for both business and leisure travelers, this elegant retreat offers a perfect blend of comfort, style, and convenience, ensuring a memorable stay in the heart of Pittsburgh. Nestled in a prime location, our unit provides easy access to the city’s top attractions, making it the ideal base for exploring everything Pittsburgh has to offer *ID and Background verification needed *

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.
Popular amenities for Shadyside holiday rentals
Stay near Shadyside's top sights
Other great holiday rentals in Shadyside

Shadyside/Central @4 Stylish&Central Studio w/Prkg

Bright & Upscale|King Bed|Free Parking w/Workspace

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

Cozy 2BR steps from Walnut St!

Upscale King Suite by WholeFoods

Upscale King Bed Suite |ADA w/ Free parking!

Stunning 2 BR King Bed Suite ~ Steps from Walnut

Shadyside King Suite w/ Parking!
Quick stats about holiday rentals in Shadyside

Total holiday rentals
Explore 410 holiday rentals in Shadyside

Nightly prices starting at
Shadyside holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 31,720 verified reviews to help you choose

Family-friendly holiday rentals
150 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 140 rentals that welcome pets

Rentals with dedicated workspaces
310 properties have a dedicated workspace

Wifi availability
400 of Shadyside holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Shadyside rentals

4.9 Average rating
Shadyside stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
- PNC Park
- Carnegie Mellon University
- Fallingwater
- Seven Springs Mountain Resort
- Acrisure Stadium
- David Lawrence Convention Center
- Pittsburgh Zoo & PPG Aquarium
- University Of Pittsburgh
- Idlewild & SoakZone
- Ohiopyle State Park
- Raccoon Creek State Park
- Sri Venkateswara Temple
- Point State Park
- Kennywood
- Phipps Conservatory and Botanical Gardens
- National Aviary
- Schenley Park
- Stage AE
- Petersen Events Center
- Children's Museum of Pittsburgh
- Senator John Heinz History Center
- Carnegie Museum of Art
- Cathedral of Learning
- Carnegie Science Center





