Holiday houses in Shadyside, Pittsburgh

5 out of 5 average rating, 43 reviews

HULU+GYM+Parking Near Universities|UPMC|Shopping

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: 🚗FREE Street Parking for 1 Car(Based on Availability) 🏋🏻‍♂️State-Of-The-Art (24/7)Fitness Center 💼Private & Co-Working Spaces 🔌Level 2 EV Charging Station Available 🍵Complimentary Tea/Coffee Station 🏓Ping Pong Table, Comfy Seating Area 🍖Outdoor BBQ 🐾Pet Friendly

5 out of 5 average rating, 8 reviews

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.

4.78 out of 5 average rating, 656 reviews

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.

Top Guest favourite

Guest suite in Highland Park

4.98 out of 5 average rating, 241 reviews

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.

4.84 out of 5 average rating, 102 reviews

Charming Shadyside 5th Ave Apt. + Parking

1st floor Only shared space is foyer. Queen bed. with sitting/dining area Bath with shower, Wi-Fi, TV. Kitchen DW, MW, range, and frig, all kitchen items. Parking for ONE car and a porch and garden to relax. Near shops, restaurants and short walk to bus stop. NO SMOKERS. Parking for small/mid-size cars/SUVS Free parking on the street one block away for vans, trucks, over-sized vehicles. Mini-split for heat/AC. Dogs permitted upon approval--$25 fee. per dog. No cleaning fee added on for room.

4.99 out of 5 average rating, 85 reviews

Betwn Ellsworth & Walnut! Sleeps4! Parking&Laundry

This remodeled apartment is in an ideal location in Shadyside just a short walk to CMU, Pitt, Walnut Street and much more! My apartment features a deck, open-concept layout, bedroom with a walk-in closet, central air, and free laundry. One parking spot is available IF RESERVED IN ADVANCE. The apartment sleeps 4 people. The bedroom has a queen bed. The living room has a sofa couch that very conveniently folds down to transform into a queen-sized bed. The spacious deck is great for relaxing.

4.89 out of 5 average rating, 168 reviews

Cozy King suite! $0 cleaning fee

Brand new listing! 1 BR/ 1 bath apartment in a prime location steps away from Walnut street with plenty of restaurants, shops, coffee shops & UPMC Shadyside hospital! Fully equipped for both long and short stays. - King bed (memory foam mattress) - Sleeper sofa - 24/7 Guest communication - Pet friendly - Fully stocked kitchen - Smart Home Technologies - Central AC/ Heat - Free street parking - Speedy wifi & desk - Free washer/ dryer Message today to secure your reservation!

4.91 out of 5 average rating, 11 reviews

Lux King Bed | Free Parking + Gym | UPMC+CMU+Pitt

✨ Welcome to our large, stylish studio in the heart of Shadyside! This modern, fully furnished suite features sleek décor, a fully equipped kitchen, a cozy living space, and a 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

4.91 out of 5 average rating, 180 reviews

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

Unique 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.

4.86 out of 5 average rating, 14 reviews

#6 - Lovely one bedroom in the heart of Shadyside

Welcome to Shadyside STAY! This lovely 1 bedroom apartment is located in the ideal central location of Shadyside, situated right on 5th Ave and Ivy Street. It’s only 5 short blocks to grab your favorite coffee or shop at Lululemon or Apple store on Walnut St. In close proximity to CMU, PITT, and UPMC Shadyside making it an ideal place for students, professors, and traveling nurses. CMU’s free shuttle stop is in front of the building, or you can walk to CMU and PITT campus.

4.88 out of 5 average rating, 179 reviews

Apartment in Bloomfield

NEW * Apt A Bloomfield/Shadyside & free parking

Ground floor Entire apartment with one bedroom, living room, bathroom is located in Bloomfield and trendy Shadyside. 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. Walking distance from UPMC Shadyside (500 ft), Hillman Cancer Center (3 houses down), West Penn Hospital (10 minutes walk, 0.4 mile), within CMU & Pitt shuttle route.

4.9 out of 5 average rating, 446 reviews

Apartment in Friendship

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).

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Stay near Shadyside, Pittsburgh's top sights

Carnegie Mellon University11 locals recommend

Phipps Conservatory and Botanical Gardens100 locals recommend

Carnegie Museum of Art58 locals recommend

Other great holiday rentals in Shadyside, Pittsburgh

4.91 out of 5 average rating, 110 reviews

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

StevenRating, 5 stars2 weeks ago

This was a perfectly pleasant space in a charming neighborhood with lots of restaurants and stores in easy walking distance. Visitors should be aware that this is a basement apartment in a large house. (In retrospect, this should have been obvious from the photographs.)

4.82 out of 5 average rating, 197 reviews

Apartment in Friendship

PRIVATE MINI STUDIO IN BRIGHT NEW BASEMENT (B2)

NicholasRating, 5 stars1 week ago

really simple but clean and homey vibe. the place was very easy to find, very clean and close to grocery and places to eat.

4.82 out of 5 average rating, 277 reviews

Chic & Cozy 2BR | Walkable Shadyside Location

DeanRating, 5 stars3 days ago

Jake focuses on the important things - ultra-comfortable beds with great sheets. Top notch towels. And amazing communication. This apartment is really great and ideally situated in Shadyside, just a few blocks from trendy Walnut St. and within walking distance to several of Pittsburgh's best restaurants, including a dive bar with the best food, cocktails, and punk rock playlist (Kelly's Bar and Lounge).

Top Guest favourite

Apartment in East Liberty

4.96 out of 5 average rating, 113 reviews

Upscale King Suite by WholeFoods

MonikaRating, 5 stars3 days ago

This place was great! Looks like the pictures and very clean! You can hear the neighbor upstairs at times so I would recommend some ear plugs. We really enjoyed the place and it had everything we needed! Lots of space. Bonus was that there was a designated parking spot and washer and dryer. We will definitely stay here again!