Holiday rentals in Shadyside

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Top-rated holiday rentals in Shadyside

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
The modern kitchen features sleek wood cabinetry and stainless steel appliances, including a microwave and dishwasher. A small dining area is visible through the glass door leading to a balcony. Essentials like a kettle and coffee maker are positioned on the countertop.
Flat in Shadyside
4.99 out of 5 average rating, 71 reviews

GYM+HULU with Parking Near UPMC|Shopping|Pitt Uni

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

Top guest favourite
The exterior entrance of the apartment is shown, featuring a short path lined with greenery. A wooden ramp leads up to the door, surrounded by various plants, creating a welcoming and natural entrance. The door is framed with a glass panel, allowing light to enter.
Flat in East Liberty
4.97 out of 5 average rating, 146 reviews

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.

Top guest favourite
The exterior of a sunporch suite is displayed, featuring large wall-to-wall windows framed by white columns. A pathway leads to the entrance, surrounded by lush greenery, including a bush. The home showcases a charming blend of white and red brick, adding character to the facade.
Guest suite in Highland Park
4.98 out of 5 average rating, 279 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.

Guest favourite
Private room in Squirrel Hill North
4.94 out of 5 average rating, 135 reviews

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).

Guest favourite
A cozy bedroom space features a green upholstered headboard with a red accent pillow atop a neatly made bed. A minimalist bedside table holds a small plant and a decorative book. Framed artwork adorns the wall above, contributing to a calm atmosphere.
Flat in Shadyside
5 out of 5 average rating, 16 reviews

King Bed | Free Parking | Near UPMC, Pitt & CMU

✨ Welcome to our stylish and modern apartment in the heart of Shadyside! This fully furnished 1 bedroom suite features sleek décor, a fully equipped kitchen, cozy living space and luxurious king bed. Enjoy top-tier amenities, including: 🔹 Free Street Parking 🔹 Fitness Center & Yoga Studio 🔹 Complimentary Coffee Station 🔹 Variety of Co-Working Spaces 🔹 Resident Clubroom with TV 🔹 Courtyard with BBQ & Ping Pong Table 🔹 EV Charging Station 🔹 On-Site Secure Parking Available

Superhost
The private room features a wooden bed frame with a soft grey blanket laid over the queen bed. Natural light illuminates the space from a nearby lamp. Two framed botanical prints hang above the nightstand. A sleek white chair and desk are visible in the corner.
Private room in North Oakland
4.95 out of 5 average rating, 177 reviews

Oakland/University @B Quiet & Stylish Private Bd

Cozy and Stylish private room close to Oakland, Shadyside, Bloomfield and Friendship, steps to Universities. A modern design features a queen bed, shared bathroom, working desk. Free Street Parking is available and instructions to obtain a parking pass will be provided on check in date. Please check full listing description for more details and shared amenities. Walk to grocery store, restaurants, hospitals and universities. Perfect for savvy budget travellers who deserve quality stay.

Guest favourite
Private room in Shadyside
5 out of 5 average rating, 14 reviews

Shadyside/Pittsburgh @A Modern & Cozy Private BD

Spacious & Cozy private room with a central location in Shadyside, located minutes to UPMC Hospitals, Universities, Walnut St. Enjoy the proximity to shopping, bars & restaurants. A modern design features a king bed, shared bathroom, working desk. Free Private Parking is available. Please check full listing description for more details and shared amenities. Walk to grocery store, restaurants, hospitals and universities. Perfect for savvy budget travelers who deserve quality stay.

Guest favourite
The spacious bedroom features a wooden platform bed with a plush mattress and white linens, complemented by a decorative blanket. A minimalist bedside table holds a lamp, while two framed botanical prints adorn the wall. Natural light filters through the window, enhancing the inviting atmosphere.
Flat in Shadyside
4.96 out of 5 average rating, 121 reviews

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.

Guest favourite
A modern kitchen area features sleek cabinetry alongside a wooden countertop and stainless-steel appliances. A spacious gray sofa with decorative pillows is situated nearby, providing a comfortable seating option. Light streams through a window, illuminating the tiled floor and brick accent wall.
Flat in Friendship
4.9 out of 5 average rating, 471 reviews

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).

Superhost
The bedroom features a spacious king bed with a memory foam mattress, accompanied by a plush blanket. A large window allows natural light to fill the room, complemented by stylish curtains. An office desk with a chair and a lamp are present, along with a closet and bedside table.
Flat in Shadyside
4.84 out of 5 average rating, 276 reviews

🔥Pristine King Bed Suite ⚡️ Hidden Gem 💎 PITT / CMU ✨ Pet Friendly 🐶

Pristine 1 bedroom apartment in the heart of Shadyside! Prime location, short walk to plenty of restaurants, shops, coffee shops & UPMC Shadyside hospital! Fully equipped for both long and short stays. 🔹King bed (memory foam mattress) 🔸Pet friendly! 🐶 🔹Fully stocked & equipped kitchen 🔸Smart Home Technologies 🔹Central AC/ Heat 🔸Luxurious waterfall shower head🚿 🔹Free street parking 🔥Message today to secure your reservation!🔥

Guest favourite
A bright and spacious studio unit features a Queen-sized bed with plush bedding and decorative pillows. A neutral area rug complements the flooring, while closet doors and wall art add to the modern decor. Natural light enhances the welcoming ambiance of the room.
Flat in Shadyside
4.91 out of 5 average rating, 46 reviews

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 *

Guest favourite
A spacious bedroom is equipped with a queen bed covered in a light blue duvet. Natural light filters through the window with sheer curtains, illuminating a small desk and chair. A cozy couch with a patterned design completes the inviting space.
Private room in Shadyside
4.94 out of 5 average rating, 105 reviews

Shadyside Private Bed/Bath, Office, Free Parking

Heart of Shadyside - short walk to Walnut Street or Shadyside Hospital. One block to bus stop, grocery store, restaurants. Comfortable spacious bedroom with queen bed in townhome. Private bathroom with shower stall. TV, wifi, microwave, mini-fridge, coffee maker, dresser, large closet. Access to washer/dryer. Small desk and office chair. Additional loft workspace with docking station. Driveway parking.

Popular amenities for Shadyside holiday rentals

When is the best time to visit Shadyside?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price₹7,104₹7,193₹7,814₹8,702₹10,034₹10,300₹8,880₹9,235₹9,324₹9,235₹8,791₹7,992
Avg. temp-2°C0°C4°C11°C16°C21°C23°C22°C18°C12°C6°C1°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 ₹2,664 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!

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