
Holiday rentals in Shadyside
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Top-rated holiday rentals in Shadyside
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Meade Street Apartment Near Chatham U , Pitt & CMU
Enjoy your stay in Pittsburgh in style and comfort in this unique apartment with touches of the old and new! This stylish retreat is located in the heart of Pittsburgh in Point Breeze North near Chatham University and Pitt. This one-of-a-kind apartment will greet you with the timeless charm of beautiful woodwork and flooring, seamlessly blending classic elegance with modern comfort. Situated on the 2nd floor, this inviting residence offers comfort, convenience, & a fantastic location. Book now!!

UPMC|Shopping+HULU Near Universities|PARKING+GYM
Discover comfort and convenience in our charming city haven. Perfect for professionals and travelers, our apartment is your gateway to nearby dining, boutique stores, shopping outlets, & attractions. Building amenities include: đFREE Street Parking for 1 Car(Based on Availability) đđťââď¸State-Of-The-Art (24/7)Fitness Center đźPrivate & Co-Working Spaces đLevel 2 EV Charging Station Available đľComplimentary Tea/Coffee Station đPing Pong Table, Comfy Seating Area đOutdoor BBQ đžPet Friendly

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.

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.

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 & 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.

Chic & Cozy 2BR | Walkable Shadyside Location
Fresh 2 BR apartment in the heart of Shadyside! Prime location, steps from UPMC Shadyside & Walnut Street! Fully equipped for either a long or short stay! đKing Bed (Memory foam mattress) âď¸Queen Bed (Memory foam mattress) đPet friendly! âď¸Central AC/ Heat đFully stocked & equipped kitchen âď¸Luxurious waterfall shower head đTwo Smart TVs âď¸Free Street parking đLaundry (Shared & Free) âď¸Pull out bed (Full) đĽMessage today to secure your reservation!đĽ

PRIVATE MINI STUDIO (D1)
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).

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 cityâs top attractions, making it the ideal base for exploring everything Pittsburgh has to offer *ID and Background verification needed *

#6 - Lovely one bedroom in the heart of Shadyside
Welcome to Shadyside STAY, your cozy home base in Pittsburghâs most walkable neighborhood. Just steps from Walnut Streetâs coffee shops and boutiques, and minutes from CMU, Pitt, and UPMC Shadyside. CMUâs 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

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

PRIVATE MINI STUDIO IN BRIGHT NEW BASEMENT (A)

Shadyside/Central @4 Stylish&Central Studio w/Prkg

PRIVATE FULL STUDIO IN PITTSBURGH (C2)

Huge Open Concept 2BR by Walnut

PRIVATE MINI STUDIO IN BRIGHT NEW BASEMENT (B2)

PRIVATE MINI STUDIO (C1)

Upscale King Bed Suite |ADA w/ Free parking!

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 | $104Â SGD | $106Â SGD | $115Â SGD | $128Â SGD | $147Â SGD | $151Â SGD | $137Â SGD | $147Â SGD | $138Â SGD | $136Â SGD | $129Â SGD | $117Â SGD |
| 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 $39Â SGD 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 â averaging 4.9 out of 5!
Destinations to explore
- House rentals Shadyside
- Fitness-friendly rentals Shadyside
- Flat rentals Shadyside
- Pet-friendly rentals Shadyside
- Rentals with a patio Shadyside
- Rentals with outdoor seating Shadyside
- Family-friendly rentals Shadyside
- Rentals with an EV charger Shadyside
- Rentals with a washing machine and dryer Shadyside
- Rentals with a fireplace Shadyside
- Carnegie Mellon University
- PNC Park
- Strip District
- 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
- Point State Park
- Phipps Conservatory and Botanical Gardens
- Fox Chapel Golf Club
- Carnegie Museum of Art
- Narcisi Winery
- Senator John Heinz History Center
- Schenley Park
- Children's Museum of Pittsburgh
- Bella Terra Vineyards
- Cathedral of Learning
- Laurel Mountain Ski Resort




