
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.

Historic Sunporch Suite
Welcome! We are delighted to share with you our favorite room in an 1895 Georgian Colonial home. This comfortable sunporch suite is ideal for two guests or a family with a young child. Located in a safe, quiet, and wonderful section of Pittsburgh, we are close to the zoo and Children's Hospital, and a short drive from downtown. This suite has its own separate entrance, bathroom, and kitchenette. The wall-to-wall windows look over the front yard, courtyard, and our neighbor's Victorian home.

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!

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!

Quaint cozy Shadyside One Bedroom
Cozy apartment located in Shadyside.Just steps away from Shadyside Hospital, this apartment is great for long or short term visitors.Grocery stores, restaurants, bars, and shops are all just a few minute walk from this apartment as well. The apartment is a short drive to Heinz Field, PPG Paints Arena, PNC Park, and all the amazing museums Pittsburgh has to offer! Also near by is CMU, PITT, Chatham Univeristy, and Carlow College.Free parking & WiFi.Towels,bed linens,toilet paper provided.

Victorian home 2 bedroom Shadyside
Bright, sunny, spacious 2 bedroom apartment with 1 parking space in the heart of Shadyside. This apartment is in a Victorian home on a quiet street. There is a train that runs below the street I feel it is part of the history and charm of city living. Shopping, restaurants, UPMC hospitals, Universities, museums and cultural activities, within walking distance or public transportation. The unit has been recently updated, beautiful new bathroom and hardwood flooring through out.

A Home In The Heart of Shadyside
Cozy 1 bedroom home steps from Walnut St. It's a little bit rough and a little bit refined (it's our latest work in progress). Its our home and we travel a lot, so we love to share our space with others. Walker's paradise; and very bike-able, with city bikes a block away. AC and heating. * Quiet, safe, and beautiful tree-lined streets * Carnegie Mellon University and East liberty- 6 min by bicycle * University of Pittsburgh - 9 min by bicycle * Shared courtyard and front porch

Shadyside/Pittsburgh, Modern & Stylish 1BD, w/Prkg
Stylish 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.

PRIVATE MINI STUDIO IN BRIGHT NEW BASEMENT (A)
This Bright basement studio is for anyone needing a stylish, clean place to stay while visiting Pittsburgh. It has a new queen bed, sleeper sofa, desk, bar and a very large bathroom. It has a private entrance at the back of a beautiful 1890s Pittsburgh mansion. It works very well for travelers 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 Entire APT B Friendship Park & Free Parking
Ground Floor Entire apartment with one bedroom, living room, bathroom is located in Bloomfield, a quiet yet vibrant neighborhood that’s central to all the best attractions. It features off Street parking , a rare find in the central city. This space has 1 bedroom with a queen bed, a well equipped kitchen, and a luxurious bathroom & shower. 🎈Smart lock w/ private entrance 🎈Luxurious waterfall shower head 🎈private parking lot 🎈Full equipped kitchen

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*

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

Cozy & Central 2BR ~ Steps from Walnut St!

Shadyside 2Bed 2Bath w/ Parking!

PRIVATE FULL STUDIO IN PITTSBURGH (C2)

Cozy 2BR steps from Walnut St!

Cozy King Suite|Central, Workspace + Free Parking

Upscale King Suite by WholeFoods

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

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$16,737 GYD | G$16,947 GYD | G$18,411 GYD | G$20,503 GYD | G$23,642 GYD | G$24,269 GYD | G$21,968 GYD | G$23,642 GYD | G$22,177 GYD | G$21,759 GYD | G$20,713 GYD | G$18,830 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 320 vacation rentals in Shadyside

Nightly prices starting at
Shadyside vacation rentals start at G$6,277 GYD per night before taxes and fees

Verified guest reviews
Over 27,330 verified reviews to help you choose

Family-friendly vacation rentals
110 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 110 rentals that welcome pets

Rentals with dedicated workspaces
250 properties have a dedicated workspace

Wi-Fi availability
320 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
- Rentals with an EV charger Shadyside
- Rentals with a washer and dryer Shadyside
- Rentals with outdoor seating Shadyside
- Family-friendly rentals Shadyside
- Rentals with a patio Shadyside
- Rentals with a fireplace Shadyside
- Fitness-friendly rentals Shadyside
- Apartment rentals Shadyside
- Pet-friendly rentals Shadyside
- House rentals Shadyside
- PNC Park
- Strip District
- Carnegie Mellon University
- Fallingwater
- Seven Springs Mountain Resort
- Pittsburgh Zoo & PPG Aquarium
- Idlewild & SoakZone
- Oakmont Country Club
- Yellow Creek State Park
- Raccoon Creek State Park
- Kennywood
- National Aviary
- Ohiopyle State Park
- Phipps Conservatory and Botanical Gardens
- Point State Park
- Fox Chapel Golf Club
- Carnegie Museum of Art
- Narcisi Winery
- Schenley Park
- Children's Museum of Pittsburgh
- Senator John Heinz History Center
- Bella Terra Vineyards
- Laurel Mountain Ski Resort
- Randyland




