
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.

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!

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.

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.

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

Shadyside/Pittsburgh, Modern & Cozy 1BD w/Prkng
Modern and family oriented 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.

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!

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).

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 *

Cozy 2BR steps from Walnut St!
2 bedroom/ 1 bathroom apartment in the heart of Shadyside, steps from Walnut Street! 🌟2 Memory foam queen beds (Nectar Mattresses!) 🌟Spacious living room with pull out bed 🌟24/7 guest support 🌟Fully stocked & equipped kitchen 🌟Private washer/ dryer 🌟Super comfy furnishings throughout We're here for you before, during and after your stay! Reach out if you have any questions or feel free to book instantly.

Shadyside King Suite w/ Parking!
Stylish 1BR/1 bath apartment with off street parking in the heart of Shadyside, steps to Walnut St -- DESIGNATED OFF STREET PARKING! Short Walk to UPMC & West Penn hospitals, close to CMU & Pitt! The building was gutted and entirely remodeled, everything down to the soundproofing and top of the line appliances are brand new! Granite kitchen, Free laundry included inside the unit, 70inch 4K TV!
Popular amenities for Shadyside holiday rentals
Stay near Shadyside's top sights
Other great holiday rentals in Shadyside

Cozy King Suite Just off Walnut

New King Suite by Whole Foods!

Huge Open Concept 2BR by Walnut

Cozy King Suite|Central, Workspace + Free Parking

Stunning 2 BR King Bed Suite ~ Steps from Walnut

Cozy King Suite with Parking!

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

Huge King Suite Just off 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





