
Holiday houses in Shadyside
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Top-rated holiday 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.

Spacious Double King bed Penthouse Suite
Discover the charm of our cozy 2-bedroom penthouse suite in the friendly Shadyside neighborhood. This newly renovated retreat is a short distance from all that Pittsburgh has to offer! Steps away from Pittsburgh's Favorite coffee shop - Yinz Coffee! 💫 2 King beds w/ desks in each bedroom 💫 Pet friendly 💫 24/7 Guest support 💫 Free off-street parking 💫 Close to CMU / Pitt *Please note this is a 3rd floor unit with no elevator, so be prepared to walk up 3 full flights of stairs (35 steps).

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.

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.

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!

PRIVATE MINI STUDIO (D2)
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 3rd 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).

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.

Cozy Entire AptA 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. The apartment was recently updated and feels fresh, spacious. This first floor space has 1 bedroom with a queen bed, a well equipped kitchen, and a luxurious bathroom & shower.

Comfy bedroom, The Run
Private bedroom for 1 person. Newly renovated 125 year old house. Former steel mill neighborhood near Pitt & CMU. Safe and plenty of free parking. Room has full size 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 full shared bathrooms. Freeway behind house will create some noise. Free parking on street, best if you have a car.

#6 - Lovely one bedroom in the heart of Shadyside
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 pros, and visiting parents, our apartments blend classic Pittsburgh charm with fresh, modern vibes
Popular amenities for Shadyside holiday rentals
Stay near Shadyside's top sights
Other great holiday rentals in Shadyside

PRIVATE MINI STUDIO IN BRIGHT NEW BASEMENT (A)

Shadyside 2Bed 2Bath w/ Parking!

Cozy 2BR steps from Walnut St!

Cozy King Suite|Central, Workspace + Free Parking

PRIVATE MINI STUDIO (C1)

Upscale King Bed Suite |ADA w/ Free parking!

Huge 1-Bedroom Apartment In Pittsburgh (B1)

Quaint cozy Shadyside One Bedroom
When is the best time to visit Shadyside?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $138 NZD | $140 NZD | $152 NZD | $169 NZD | $195 NZD | $200 NZD | $181 NZD | $195 NZD | $183 NZD | $180 NZD | $171 NZD | $156 NZD |
| 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 $52 NZD 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 and kid-friendly amenities

Pet-friendly accommodation
Find 110 rentals that welcome pets

Rentals with dedicated workspaces
250 properties have a dedicated workspace

Wi-Fi availability
320 of Shadyside holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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 a fireplace Shadyside
- House rentals Shadyside
- Rentals with outdoor seating Shadyside
- Rentals with a patio Shadyside
- Family-friendly rentals Shadyside
- Rentals with a washing machine and dryer Shadyside
- Fitness-friendly rentals Shadyside
- Pet-friendly rentals Shadyside
- Apartment rentals Shadyside
- Rentals with an EV charger 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
- Senator John Heinz History Center
- Children's Museum of Pittsburgh
- Bella Terra Vineyards
- Laurel Mountain Ski Resort
- Cathedral of Learning




