
Holiday rentals in Shadyside
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Shadyside
Guests agree: these stays are highly rated for location, cleanliness and more.

Sunny Shadyside Condo with Private Garage
Peaceful and unique 2 bedroom, 2 bathroom loft style condo with sauna, soaking tub, private patio and garage. Located in Pittsburgh's iconic Shadyside neighborhood - just steps from Walnut Street, and some of Pittsburgh's best shopping and dining options. An 8 minute walk to UPMC Shadyside, and a 20 minute walk to Carnegie Mellon University, Bloomfield, and Friendship. Direct airport bus stops 3 blocks from house. Due to the layout of the condo, the space is not ideal for small children.

Upscale Double King Suite~Steps to Walnut~Parking!
2 OFF STREET PARKING SPACES INCLUDED FOR FREE! In the heart of Shadyside! 1 Block to Walnut St Short Walk to UPMC & West Penn hospitals, CMU & Pitt! 2BR (+sofa bed)/1bath apartment w/ private balcony in a prime location, restaurants, shops, coffee shops, & fitness studios close by. The building was gutted and remodeled, everything down to the studs is brand new! Free laundry included inside the unit. Fully stocked for both long and short term stays! Reach out to book your stay today!

Private Room in Pittsburgh near Carnegie Mellon
Cozy private room in Squirrel Hill. The apartment is shared with myself and my roomate. We keep to ourselves as we are busy working, researching, and out of the house a lot in the evenings. However, we are here to answer any questions you may have about the house or the city of Pittsburgh! The private room includes: a microwave, mini refrigerator,Keurig and coffee pods, TV, Roku, a wardrobe,blackout curtains, desk, an adjustable bed, towels, & washcloths and an AC (excluding fall/winter).

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.

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 & Quiet 1BD w/Prkng
Modern, quiet 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.

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!

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

PRIVATE MINI STUDIO (C1)
This Mini Studio is for anyone needing a neat, clean, cool place to stay. It has a new queen bed, sleeper sofa, a kitchenette and a full bathroom with a private entrance on the 2nd 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 *

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.

Spacious bedroom, The Run
Private bedroom for 1 or 2 persons. Newly renovated 125 year old house. Former steel mill neighborhood near Pitt & CMU. Safe and plenty of free parking. Room has queen bed, desk and window fan. Room is in house with 2 other Airbnb rooms with guests. Room is upstairs, steep stairs to 2nd floor. Two shared full bathrooms. Freeway behind the house creates some noise. Free parking on street, best if you have a car.
Popular amenities for Shadyside holiday rentals
Stay near Shadyside's top sights
Other great holiday rentals in Shadyside

Luxurious 2Bed by Whole Foods

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

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

Huge Open Concept 2BR by Walnut

PRIVATE MINI STUDIO IN BRIGHT NEW BASEMENT (B2)

PRIVATE MINI STUDIO (D2)

Betwn Walnut & Ellsworth! Sleeps4! Parking&Laundry

Upscale King Bed Suite |ADA w/ Free parking!
When is the best time to visit Shadyside?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £61 | £61 | £67 | £74 | £85 | £88 | £79 | £85 | £80 | £79 | £75 | £68 |
| 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 holiday rentals in Shadyside

Total holiday rentals
Explore 320 holiday rentals in Shadyside

Nightly prices starting at
Shadyside holiday rentals start at £23 per night before taxes and fees

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

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

Pet-friendly holiday rentals
Find 110 rentals that welcome pets

Rentals with dedicated workspaces
250 properties have a dedicated workspace

Wifi availability
320 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
- Rentals with an EV charger Shadyside
- House rentals Shadyside
- Flat rentals Shadyside
- Rentals with a patio Shadyside
- Family-friendly rentals Shadyside
- Rentals with a fireplace Shadyside
- Rentals with outdoor seating Shadyside
- Fitness-friendly rentals Shadyside
- Pet-friendly rentals Shadyside
- Rentals with a washing machine and dryer 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
- Cathedral of Learning
- Laurel Mountain Ski Resort




