
Vacation rentals in Shadyside
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Top-rated vacation rentals in Shadyside
Guests agree: these stays are highly rated for location, cleanliness, and more.

Cozy warm lovely Squirrel Hill free park & wifi
Situated in the heart of Squirrel Hill, all sorts of dining, theater, shopping and parks are within a short safe walking distance. Explore the incredible variety of Chinese, Korean, Mexican, Jewish, Italian, Indian foods that reside in our neighborhood. CMU, Pitt, Chatham, Duquesne & Oakland are close by bus. Frick Park w/ endless trails is under a mile away. Phipps Conservatory & Schenley Park are a 7 min drive. Just over 10 min drive to The Strip, Mount Washington, Monongahela Incline.

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 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.

Private Room Near Carnegie Mellon University-Twin
Cozy private room in Squirrel Hill. Typically, the apartment is shared with 1 additional guest and a tenant. Host may pop up to clean the apartment/additional room during your stay. The private room includes: a twin bed, microwave, mini refrigerator, TV, Roku, portable desk, twin bed, towels, washcloths and an Air Conditioner. There is a cat on the property, but most times she will be in the tenant's room. You may not even see the cat. If allergic to cats, I would not book this listing.

A Home In The Heart of Shadyside
Cozy 1 bedroom home steps from Walnut St. It's a little bit rough and a little bit refined (it's our latest work in progress). Its our home and we travel a lot, so we love to share our space with others. Walker's paradise; and very bike-able, with city bikes a block away. AC and heating. * Quiet, safe, and beautiful tree-lined streets * Carnegie Mellon University and East liberty- 6 min by bicycle * University of Pittsburgh - 9 min by bicycle * Shared courtyard and front porch

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.

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!

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.

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).

Sunny Friendship "Treehouse" 2 story / 1BD gem
Friendship Treehouse: Walking distance to 3 hospitals, our private, 2 story apartment w/ separate entry is steps away from great restaurants, coffee shops, yoga studios, art galleries & major bus lines. Located on a quiet tree-lined street in the aptly named Friendship area, we are an easy commute to Pitt & CMU. Our apartment is perfect for all of your travel & work needs. Suited for solo travelers, couples, and business travelers.

Betwn Walnut & Ellsworth! Sleeps4! Parking&Laundry
LOCATION! LOCATION! This apartment is approx 200 feet to Ellsworth Avenue and approx 700 feet to Walnut Street! My apartment features a deck, open-concept layout, central air, and free laundry. One parking spot is available for free, if reserved in advance. Please see the parking policy below. The apartment sleeps 4 people. The bedroom has a queen bed. The living room has a sofa that conveniently folds down into a queen-sized bed.

Fully renovated 2BD APT in Shadyside
Welcome to Shadyside STAY, your cozy home base in Pittsburgh’s most walkable neighborhood. Just steps from Walnut Street’s coffee shops and boutiques, and minutes from CMU, Pitt, and UPMC Shadyside. CMU’s free shuttle stops right outside, making campus access effortless. Perfect for students, professors, young pros, and visiting parents, our apartments blend classic Pittsburgh charm with fresh, modern vibes.
Popular amenities for Shadyside vacation rentals
Stay near Shadyside's top sights
Other great vacation rentals in Shadyside

Huge Open Concept 2BR by Walnut

Cozy King Suite|Central, Workspace + Free Parking

PRIVATE MINI STUDIO (C1)

Shadyside/Pittsburgh, Modern&Accessible 2BD w/Prkg

Betwn Ellsworth & Walnut! Sleeps4! Parking&Laundry

Quaint cozy Shadyside One Bedroom

High End 3 King 2Bath Apt~Parking~Steps to Walnut!

Shadyside/Pittsburgh, Modern & Stylish 1BD, w/Prkg
When is the best time to visit Shadyside?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $110 CAD | $111 CAD | $121 CAD | $135 CAD | $155 CAD | $159 CAD | $144 CAD | $155 CAD | $146 CAD | $143 CAD | $136 CAD | $124 CAD |
| 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 vacation rentals in Shadyside

Total vacation rentals
Explore 320 vacation rentals in Shadyside

Nightly prices starting at
Shadyside vacation rentals start at $41 CAD per night before taxes and fees

Verified guest reviews
Over 27,330 verified reviews to help you choose

Family-friendly vacation rentals
110 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 110 rentals that welcome pets

Rentals with dedicated workspaces
250 properties have a dedicated workspace

Wifi availability
320 of Shadyside vacation 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!
Destinations to explore
- Rentals with an EV charger Shadyside
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- Rentals with a washer and dryer Shadyside
- Family-friendly rentals Shadyside
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- House rentals Shadyside
- Rentals with a patio Shadyside
- PNC Park
- Strip District
- Carnegie Mellon University
- Fallingwater
- Seven Springs Mountain Resort
- Pittsburgh Zoo & PPG Aquarium
- Idlewild & SoakZone
- Oakmont Country Club
- Yellow Creek State Park
- Raccoon Creek State Park
- National Aviary
- Kennywood
- Ohiopyle State Park
- Phipps Conservatory and Botanical Gardens
- Point State Park
- Fox Chapel Golf Club
- Carnegie Museum of Art
- Narcisi Winery
- Schenley Park
- Children's Museum of Pittsburgh
- Senator John Heinz History Center
- Bella Terra Vineyards
- Laurel Mountain Ski Resort
- Randyland




