
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.

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: šFREE Street Parking for 1 Car(Based on Availability) šš»āāļøState-Of-The-Art (24/7)Fitness Center š¼Private & Co-Working Spaces šLevel 2 EV Charging Station Available šµComplimentary Tea/Coffee Station šPing Pong Table, Comfy Seating Area šOutdoor BBQ š¾Pet Friendly

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 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.

Avant-Garde Escape by Walnut
Welcome to our stylish, newly-renovated home, complete with modern amenities, tasteful decor, and all-new everything. Perfectly located just steps from Walnut Streetās best restaurants, bars, and shopsāa prime base for exploring Pittsburgh! ā 2 King beds + 2 Queen beds + 5 rollaway beds or futons - can sleep 16 easily! ā Private deck ā Free Washer/Dryer ā 2 Off-Street Parking spaces (Free) ā Pack N Play & High Chair Our team is here 24/7 to support you before, during, and after your stay!

Queen Bed Suite|Heart of Shadyside|Walkable &Quiet
Stylish and freshly renovated 1 BR/ 1 bath apartment 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. āļøSuper comfy queen memory foam mattress š24/7 Guest support āļøFree off-street parking! šFully stocked & equipped kitchen āļøQueen sized pull out sofa šPet Friendly (Must provide vaccination records) āļøLaundry (Free and in-unit)

Shadyside/Central @4 Stylish&Central Studio w/Prkg
Stylish and Central family oriented modern Studio apartment with a central location in Shadyside, located minutes to UPMC Hospitals, Universities, Walnut St. Enjoy the proximity to shopping, bars & restaurants. This apartment a Studio with bathroom, kitchen 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.

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 thatās 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. šSmart lock w/ private entrance šLuxurious waterfall shower head šprivate parking lot šFull equipped kitchen

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).

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

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!

Quiet, private guest suite with garden views
Relax or work in this peaceful and centrally-located guest suite, with a private entrance through a side gate. There is free and plentiful street parking and access to multiple bus lines. Large windows and sliding doors look out on a lovely backyard and garden. The bathroom was recently renovated with a brand-new shower and cork flooring.
Popular amenities for Shadyside holiday rentals
Other great holiday rentals in Shadyside

PRIVATE FULL STUDIO (G2)

Bright & Upscale|King Bed|Free Parking w/Workspace

Huge Open Concept 2BR by Walnut

PRIVATE MINI STUDIO (D2)

Chic & Cozy 2BR | Walkable Shadyside Location

Cozy King Suite|Central, Workspace + Free Parking

Cozy King Suite with Parking!

Modern & Upscale King Bed Suite|Private w/Parking!
When is the best time to visit Shadyside?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $122Ā AUD | $124Ā AUD | $134Ā AUD | $150Ā AUD | $173Ā AUD | $177Ā AUD | $153Ā AUD | $159Ā AUD | $160Ā AUD | $159Ā AUD | $151Ā AUD | $137Ā AUD |
| 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 $46Ā AUD 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 guestsāaveraging 4.9 out of 5!
Destinations to explore
- Rentals with outdoor seatingĀ Shadyside
- Rentals with an EV chargerĀ Shadyside
- Rentals with a fireplaceĀ Shadyside
- House rentalsĀ Shadyside
- Rentals with a washing machine and dryerĀ Shadyside
- Fitness-friendly rentalsĀ Shadyside
- Apartment rentalsĀ Shadyside
- Pet-friendly rentalsĀ Shadyside
- Family-friendly rentalsĀ Shadyside
- Rentals with a patioĀ Shadyside
- PNC Park
- Carnegie Mellon University
- Strip District
- Fallingwater
- Seven Springs Mountain Resort
- Pittsburgh Zoo & PPG Aquarium
- Idlewild & SoakZone
- Oakmont Country Club
- Raccoon Creek State Park
- Kennywood
- Yellow Creek State Park
- National Aviary
- Ohiopyle State Park
- Phipps Conservatory and Botanical Gardens
- Fox Chapel Golf Club
- Carnegie Museum of Art
- Point State Park
- Narcisi Winery
- Schenley Park
- Senator John Heinz History Center
- Bella Terra Vineyards
- Children's Museum of Pittsburgh
- Cathedral of Learning
- Laurel Mountain Ski Resort