
Holiday houses in Shadyside
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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 $51 NZD per night before taxes and fees

Verified guest reviews
Over 34,010 verified reviews to help you choose

Family-friendly holiday rentals
150 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 140 rentals that welcome pets

Rentals with dedicated workspaces
310 properties have a dedicated workspace

Wi-Fi availability
400 of Shadyside holiday 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 holiday rentals in Shadyside
Guests agree: these stays are highly rated for location, cleanliness and more.

Cultural District new King Suite whirlpool tub
Experience Pittsburgh's Cultural District from this new king suite! You are surrounded by Pittsburgh's best restaurants, shops, steps away from the Convention Center, theaters, and more. Designed for comfort and convenience in an unbeatable location. - King bed - Whirlpool tub / shower - Equipped Kitchen & Laundry - Walk to everything - Mult garages within 5 min - 24/7 guest support Perfect for business trips, events, or weekend getaways. We're here for you before, during and after your stay!

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.

Cozy King Suite Just off Walnut
In the heart of Shadyside! 1 Block to Walnut St w/ FREE OFF STREET PARKING Short Walk to UPMC & West Penn hospitals, 3 min drive to CMU & Pitt! 1BR/1 bath apartment in a prime location, with all Shadyside has to offer just steps away! Enjoy dozens of restaurants, shops, coffee shops, and fitness studios close by. The building was gutted & entirely remodeled in March 2024, everything down to the soundproofing, granite kitchen, and top of the line appliances & in-unit laundry is brand new!

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 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! No pets are permitted.

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.

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.

Shadyside/Central @4 Stylish&Central Studio w/Prkg
Stylish and Central family oriented modern Studio apartment with a central location in Shadyside, located minutes to UPMC Hospitals, Universities, Walnut St. Enjoy the proximity to shopping, bars & restaurants. This apartment a Studio with bathroom, kitchen 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.

King Bed | Free Parking | Gym | UPMC, Pitt & CMU
✨ Welcome to our large, stylish studio in the heart of Shadyside! This modern, fully furnished suite features sleek décor, a fully equipped kitchen, a cozy living space, and a 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

Spacious 1 bd in Shadyside - Walk to CMU and Pitt
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.

Hot Tub, King Bed, Cabin Vibes in Lawrenceville!
With cozy cabin vibes, exposed brick, and designer touches, this romantic getaway is perfect for couples or a relaxing stay. Escape to a rustic-modern retreat in the heart of Lawrenceville, just one block from Butler Street! Unwind in the private hot tub, snuggle up on the couch by the fireplace, or explore the city's best dining and nightlife just steps away. Completely remodeled in January 2025 with luxe amenities—book now for an unforgettable stay!

Cozy Apt +Gym+ EV+Free onsite Parking+ Near UPMC
Welcome to our stunning luxury 1-bed studio unit. Perfect for both business and leisure travellers, 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 *
Popular amenities for Shadyside holiday rentals
Stay near Shadyside's top sights
Other great holiday rentals in Shadyside

Walk to Walnut St | 2BR 2BA PiTT CMU UPMC

Chic Shadyside Apt w/ Balcony-1Block to Walnut St!

Luxurious Double KING~Steps to Walnut St~PARKING

Cozy King Suite with Parking!

Cozy King suite! $0 cleaning fee

Huge King Suite Just off Walnut

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

Stunning 2 BR King Bed Suite ~ Steps from Walnut
Destinations to explore
- PNC Park
- Acrisure Stadium
- Fallingwater
- Carnegie Mellon University
- Seven Springs Mountain Resort
- University Of Pittsburgh
- David Lawrence Convention Center
- Pittsburgh Zoo & PPG Aquarium
- Ohiopyle State Park
- Sri Venkateswara Temple
- Idlewild & SoakZone
- Raccoon Creek State Park
- Moraine State Park
- Stage AE
- Point State Park
- Phipps Conservatory and Botanical Gardens
- Petersen Events Center
- Schenley Park
- Kennywood
- Carnegie Science Center
- National Aviary
- Children's Museum of Pittsburgh
- PPG Paints Arena
- Senator John Heinz History Center





