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

Cozy One-Bedroom East Side Apartment
Spacious and comfortable one-bedroom apartment centrally located in the East End (East Side) of Pittsburgh. Cozy bedroom, full kitchen, bathroom, living room, and dining area. Quiet neighborhood; close to restaurants, supermarkets, coffee shops, bars, East Liberty Transit Center. On bus lines for easy access around town. The apartment is also located on the bus line to Pittsburgh Paints Arena and is about a 20-minute drive to PNC Park and Heinz Field. Great for couples, solo travelers, LGBTQIA.

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!

Upscale Double King Bed Suite ~ Steps from Walnut!
Upscale 2 bedroom/ 1 bathroom APT 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. ⭐️Two Memory foam king beds 🌟24/7 Guest Support ⭐️In-unt Washer/ Dryer 🌟Fully stocked & equipped kitchen ⭐️Sleeper sofa (Full) 🌟Pet Friendly (Most provide vaccination records) ⭐️Private entrance & front porch ⭐️Steps from popular Walnut Street!

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.

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.

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 *

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

Cozy King Suite Just off Walnut

Shadyside 2Bed 2Bath w/ Parking!

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

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

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

Upscale King Suite by WholeFoods

Stunning 2 BR King Bed Suite ~ Steps from Walnut

Cozy King Suite with Parking!
When is the best time to visit Shadyside?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$20,502 GYD | G$19,874 GYD | G$19,874 GYD | G$20,502 GYD | G$23,640 GYD | G$24,267 GYD | G$21,966 GYD | G$23,640 GYD | G$22,175 GYD | G$25,523 GYD | G$24,895 GYD | G$20,293 GYD |
| Avg. temp | -2°C | 0°C | 4°C | 11°C | 16°C | 21°C | 23°C | 22°C | 18°C | 12°C | 6°C | 1°C |
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$6,276 GYD per night before taxes and fees

Verified guest reviews
Over 31,720 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

4.9 Average rating
Shadyside stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Family-friendly rentals Shadyside
- Rentals with outdoor seating Shadyside
- Rentals with a fire pit Shadyside
- Fitness-friendly rentals Shadyside
- House rentals Shadyside
- Rentals with a patio Shadyside
- Apartment rentals Shadyside
- Pet-friendly rentals Shadyside
- Rentals with a fireplace Shadyside
- Rentals with a washer and dryer Shadyside
- Rentals with an EV charger Shadyside
- PNC Park
- Carnegie Mellon University
- Fallingwater
- Seven Springs Mountain Resort
- David Lawrence Convention Center
- Acrisure Stadium
- Pittsburgh Zoo & PPG Aquarium
- University Of Pittsburgh
- Idlewild & SoakZone
- Ohiopyle State Park
- Raccoon Creek State Park
- Point State Park
- Sri Venkateswara Temple
- Kennywood
- National Aviary
- Phipps Conservatory and Botanical Gardens
- Stage AE
- Schenley Park
- Petersen Events Center
- Children's Museum of Pittsburgh
- Carnegie Museum of Art
- Cathedral of Learning
- Senator John Heinz History Center
- Randyland





