Holiday houses in Shadyside

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Quick stats about holiday rentals in Shadyside

  • Total holiday rentals

    Explore 410 holiday rentals in Shadyside

  • Nightly prices starting at

    Shadyside holiday rentals start at $51 NZD per night before taxes and fees

  • Verified guest reviews

    Over 34,010 verified reviews to help you choose

  • Family-friendly holiday rentals

    150 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 140 rentals that welcome pets

  • Rentals with dedicated workspaces

    310 properties have a dedicated workspace

  • Wi-Fi availability

    400 of Shadyside holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Shadyside rentals

  • 4.8 Average rating

    Shadyside stays are highly rated by guests—averaging 4.8 out of 5!

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
Apartment in Downtown Pittsburgh
4.9 out of 5 average rating, 264 reviews

Cultural District new King Suite whirlpool tub

Experience Pittsburgh's Cultural District from this new king suite! You are surrounded by Pittsburgh's best restaurants, shops, steps away from the Convention Center, theaters, and more. Designed for comfort and convenience in an unbeatable location. - King bed - Whirlpool tub / shower - Equipped Kitchen & Laundry - Walk to everything - Mult garages within 5 min - 24/7 guest support Perfect for business trips, events, or weekend getaways. We're here for you before, during and after your stay!

Top Guest favourite
Apartment in East Liberty
4.97 out of 5 average rating, 31 reviews

Friendship Penthouse • King Bed •Laundry & Parking

Friendship Penthouse: Spacious 1-Bedroom/2-Beds, King + Sleeper Sofa, In-Unit Laundry & Free Parking. Recently renovated Victorian penthouse (3rd floor, no elevator) perfect for medical travelers, university visitors, students, and extended stays. Superhost with 4.97★ rating from 30 reviews. Steps from Whole Foods, Shadyside restaurants, UPMC Shadyside; short car ride to Carnegie Mellon & Pitt. Walkable historic neighborhood with genuine character, and yes, genuinely free parking in Pittsburgh.

Top Guest favourite
An open living space features a modern kitchen with stainless steel appliances, a dining area with two stools, and a cozy seating arrangement with a brown couch and decorative pillows. A large window allows natural light to fill the area, complemented by sleek laminate flooring.
Apartment in Shadyside
4.94 out of 5 average rating, 187 reviews

Cozy King Suite Just off Walnut

In the heart of Shadyside! 1 Block to Walnut St w/ FREE OFF STREET PARKING Short Walk to UPMC & West Penn hospitals, 3 min drive to CMU & Pitt! 1BR/1 bath apartment in a prime location, with all Shadyside has to offer just steps away! Enjoy dozens of restaurants, shops, coffee shops, and fitness studios close by. The building was gutted & entirely remodeled in March 2024, everything down to the soundproofing, granite kitchen, and top of the line appliances & in-unit laundry is brand new!

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
4.98 out of 5 average rating, 110 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!

Top Guest favourite
Apartment in Shadyside
5.0 out of 5 average rating, 16 reviews

Shadyside 2 BR | Walk to Walnut + On site parking

Bright, energizing and charming 2 BDRM Shadyside apartment in Pittsburgh's most walkable neighborhood. Steps from Walnut Street's best restaurants, cafés, and boutique shops. New furniture & furnishings (work/study, too), bed 'n bath, lighting, fully equipped kitchen (even an air fryer), fast Wi-Fi, 65" TV, in-unit washer/dryer & more. Smart self-check-in, with rare off-street reserved parking (for 1 Car; also: buses nearby). Minutes to Downtown, CMU, and Pitt — your perfect in-city stay.

Top Guest favourite
Home in Shadyside
5.0 out of 5 average rating, 32 reviews

Shadyside Home - Walk to Walnut St - Free Parking

Beautifully maintained Shadyside row home one block from Walnut Street - and no cleaning fee. Bright, open living spaces, updated appliances, lots of natural light, yet quiet inside. Walk to boutiques, cafes, and restaurants; minutes to CMU, Pitt, and UPMC - ideal for campus visits, hospital stays, or weekend trips. Two off-street parking spots, a covered front porch, and a private deck. Finished basement adds a 90" TV plus flexible space for an office, playroom, or cozy movie room.

Guest favourite
A spacious private room is featured, showcasing a king bed with a foam mattress, complemented by light wood furniture. Two bedside lamps provide gentle illumination. Natural light enters through large windows, accentuating the clean, modern design of the space.
Private room in Shadyside
4.93 out of 5 average rating, 80 reviews

Shadyside/Pittsburgh @C Modern & Bright 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.

Guest favourite
Apartment in Shadyside
5.0 out of 5 average rating, 15 reviews

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

✨ 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

Top Guest favourite
The living area features a cozy couch with a decorative throw, providing a warm contrast to the exposed brick wall. A dining area with two stools is situated near the kitchen, while a large smart TV displays various streaming options.
Apartment in Shadyside
4.93 out of 5 average rating, 275 reviews

Chic Shadyside Apt w/ Balcony-1Block to Walnut St!

In the heart of Shadyside! 1 Block to Walnut St Short Walk to UPMC & West Penn hospitals, CMU & Pitt! 1BR/1 bath apartment with private covered balcony w/ TV in a prime location, dozens of restaurants, shops, coffee shops, and fitness studios close by. The building was gutted and entirely remodeled, everything down to the soundproofing and top of the line appliances are brand new! Free laundry included inside the unit. Fully stocked for both long and short term stays!

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.
Apartment in Shadyside
4.94 out of 5 average rating, 187 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
Apartment in Shadyside
4.92 out of 5 average rating, 13 reviews

StylishAttic| (600 sq ft) 2min->CMU|Walnut

I've hosted & co-hosted for 4 years. All questions are answered here so you can make an informed decision. ★ 7 min Walk to Walnut Street ★ 10 min Walk to CMU ★ 4 minutes Drive to University of Pittsburgh ★ 4 minutes Drive to UPMC Shadyside ★ 5 minutes Drive to Bakery Square ★ 8 min drive to Duquesne University ★ 10 min drive to Downtown ★ 15 min drive to Mount Washington ★ Steelers Stadium (Acrisure Stadium) We take absolute pleasure in welcoming you in our home.

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.
Apartment in Pittsburgh
4.89 out of 5 average rating, 512 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).

Popular amenities for Shadyside holiday rentals