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.

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Top Guest favourite
A modern kitchen showcases light wood cabinetry and stainless-steel appliances, including a dishwasher and an oven. An island with sleek black legs is paired with three chairs. Natural light illuminates the open layout, featuring a subtle tile backsplash and minimalist decor.
Apartment in Shadyside
5 out of 5 average rating, 58 reviews

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: šŸš—FREE Street Parking for 1 Car(Based on Availability) šŸ‹šŸ»ā€ā™‚ļøState-Of-The-Art (24/7)Fitness Center šŸ’¼Private & Co-Working Spaces šŸ”ŒLevel 2 EV Charging Station Available šŸµComplimentary Tea/Coffee Station šŸ“Ping Pong Table, Comfy Seating Area šŸ–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.
Apartment 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.

Top Guest favourite
A brick townhouse features a charming facade with multiple gabled roofs and evenly spaced windows. The entrance is accented by a wooden porch, surrounded by trees and landscaping that complement the residential setting.
Home in Shadyside
5 out of 5 average rating, 63 reviews

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 Street’s best restaurants, bars, and shops—a prime base for exploring Pittsburgh! ⭐ 2 King beds + 2 Queen beds + 5 rollaway beds or futons - can sleep 16 easily! ⭐ Private deck ⭐ Free Washer/Dryer ⭐ 2 Off-Street Parking spaces (Free) ⭐ Pack N Play & High Chair Our team is here 24/7 to support you before, during, and after your stay!

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.
Apartment 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 dĆ©cor, a fully equipped kitchen, cozy living space and luxurious king bed. Enjoy top-tier amenities, including: šŸ”¹ Free Street Parking šŸ”¹ Fitness Center & Yoga Studio šŸ”¹ Complimentary Coffee Station šŸ”¹ Variety of Co-Working Spaces šŸ”¹ Resident Clubroom with TV šŸ”¹ Courtyard with BBQ & Ping Pong Table šŸ”¹ EV Charging Station šŸ”¹ 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
A private room features a spacious bed with a striped duvet, complemented by a wooden bed frame. A wall-mounted television is positioned opposite the bed, with a window allowing natural light to enter. Minimalist dƩcor enhances the modern feel of the space.
Private room in Shadyside
5 out of 5 average rating, 27 reviews

Shadyside/Pittsburgh @H Modern & Cozy Private BD

Spacious & Bright 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 travellers who deserve quality stay.

Superhost
A spacious sleeping area is highlighted by a wooden bed with neutral bedding. A cozy fireplace is located beneath a clock, accompanied by a decorative plant and a circular seating area. Natural light enters through the windows, enhancing the room’s bright atmosphere.
Apartment in Shadyside
4.93 out of 5 average rating, 121 reviews

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.

Guest favourite
The living room features a spacious gray sectional sofa positioned near large windows that allow natural light to fill the space. A modern glass coffee table is centered on a soft area rug, while white interior doors provide access to closet space.
Apartment in Shadyside
4.89 out of 5 average rating, 186 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!

Guest favourite
A modern living area features a kitchenette with a small refrigerator and microwave, alongside a comfortable white chair and a sleek gray sofa. A wall-mounted TV displays a city skyline, while exposed brick adds a touch of character. Natural light filters in through a window.
Home in Friendship
4.88 out of 5 average rating, 532 reviews

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).

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.
Apartment 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*

Popular amenities for Shadyside holiday rentals

When is the best time to visit Shadyside?

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Avg. price$139Ā NZD$141Ā NZD$153Ā NZD$171Ā NZD$197Ā NZD$202Ā NZD$174Ā NZD$181Ā NZD$183Ā NZD$181Ā NZD$172Ā NZD$157Ā NZD
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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 $52Ā 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!

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