
House holiday rentals in Shadyside
Find and book unique houses on Airbnb
Top-rated house rentals in Shadyside
Guests agree: These houses are highly rated for location, cleanliness and more.

*e 2br A short walk to Grandview sleeps up to 4 *
Walk to spectacular Grandview Ave views from this quirky old Mt. Washington house offering great space and many nice updates! From this location you can quickly walk to the Mon incline which offers transfers to Pittsburgh's subway system called the "T" at Station Square. You can ride the T to Heinz Field, PNC Park, Rivers Casino, PPG Paints Arena, and all the downtown Pittsburgh cultural districts. You are also very close to the University of Pittsburgh, Duquesne, and CMU. Great location!

Pittsburgh, PA - North Side
Keep it simple at this peaceful and centrally-located place. This two bedroom single family home is in an optimal location for access to all Pittsburgh has to offer. Located 2 miles from Pittsburgh's downtown area and Strip District, 5 minutes from PNC Park and Heinz Field, 10 minutes from PPG Paints Arena and UPMC Hospitals, and 15 minutes from CMU, University of Pittsburgh, and Duquesne University. Minutes from Garden Cafe coffee shop, Threadbare Cider House and plenty of bars and restaurants.

Sunny, Creative Duplex in Friendship
You and your travel companions will be in an ideal Pgh spot when you stay at this Friendship neighborhood home. With 3 floors, you'll have lots of room to spread out or gather together. This beautifully updated 100-year-old home is a creative space, filled with art from Pgh artists, cheery textiles from around the world, and vintage decor scattered throughout. It’s a charming retreat for artists & writers, a cozy spot for families, or the perfect place for larger groups to share a getaway.

Bright Garfield rowhome with fenced-in yard
Walk to anything you need from this cozy, bright rowhome in Pittsburgh's Garfield neighborhood! Best for couples or remote workers, but can accommodate up to four guests. The second bedroom doubles as a workspace. There is a fenced-in backyard for guest use. 5-minute walk to Penn Ave bars, shops, restaurants, grocery stores & more. Convenient access to bus lines & surrounding neighborhoods of East Liberty, Shadyside, Bloomfield, Oakland, Lawrenceville, Highland Park, & the Strip District.

Spectacular Skyline Views - Luxury 2 Bedroom
Watch the city skyline buzz from the comfort of your couch or bed. This high end luxury home is located on Mt. Washington and close to everything Pittsburgh. Minutes walk to Southside, Downtown, Strip District, Heinz Field, and PPG Convention Center just to name a few. Super clean, comfortable, and cool with all of the amenities of your own home. Just bring your bag and make this home base while you're in the Burgh. Great for couples, friends, solo adventurers, and business travelers.

The Pitt Studio - Private entrance & parking
Welcome to Pitt Studio! This studio is located on a fully renovated basement of a 3 story house in South Oakland. This is a perfect studio for medical residents, grad students, tourists, and parents of university students who are in town for short or long-term rental. The house is located on a quiet street around families and students. The UPMC Magee Womens Hospital is 0.7 miles away, UPMC Presbyterian Hospital, 1.0 mile, and University of Pittsburgh Cathedral of Learning is 1.2 miles.

Urban serenity, privacy in charming carriage house
Carriage house apartment all to yourself. Sleeps 3. Uniquely charming. Private, quiet, and self-contained. Keypad check-in, free parking, laundry, many amenities. Responsive hosts on site. Great location in lively East End. Convenient to hospitals, restaurants, shopping, entertainment, public transportation. Ideal weekend getaway for couples. Perfect for traveling workers. Extended stay discounts for bookings of a week or more. Discounts offered for return guests; please inquire.

Urban converted gas station in heart of South Side
My place is close to art and culture, restaurants and dining, and family-friendly activities. The southside is loaded with bars and restaurants, grocery and clothing stores, galleries, public library and pool. It is very near downtown Pgh and has great bike/running trails along the river. You’ll love my place because of the outdoors space, the neighborhood, the light, the comfy bed, and the kitchen. My place is good for couples, business travelers, and furry friends (pets).

Contemporary and beautiful 1 bedroom unit
This lovely place has a style of its own. Contemporary living at its best! It is Conveniently located in Mt Washington on the bus line, walking distance to the trolly, and close to all major highways; you won’t have any issues getting around. Comes with both on and off street parking, brand new stainless steel appliances in the kitchen including a dishwasher. New furniture. Large new smart flat screen TVs in the bedroom and living room. This place is definitely a must!

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).

Quiet, Secluded Loft Suite
Completely private, spacious and secluded third floor loft suite behind a door and up a private staircase. Two bedrooms and full bathroom. Walkable, historic East End neighborhood with beautiful architecture and gardens; multiple shopping, dining, coffee and activities close by. Free street parking. No hassle entry and checkout. Responsive host. No cleaning fees.

Lawrenceville 3BR Ping-Pong Pad
Experience historic charm & modern comfort in trendy Lawrenceville! Our 3-bedroom home sleeps 8 guests with 2 OFF-STREET PARKING SPACES, a ping-pong table, Wi-Fi & a fully equipped kitchen. Explore Pittsburgh's vibrant culture & history, close proximity to lively Butler Street. Book your stay & create unforgettable memories!
Popular amenities for Shadyside house rentals
House rentals with a pool

Posh Pittsburgh ~ 2-story luxury suite & patio

A beautiful cozy home away from home!

Convenient townhome

Renovated Cozy Duplex w/pool, Close to downtown

PIT Staycation Retreat with Pool House!

4BR Victorian House in Shadyside Off of Walnut St

3BR, 2 Bath Home -Pool, Deck, near Pgh, Sleeps 10

Cozy & Beautiful Pittsburgh Home
Weekly house rentals

Foxy home, off-street parking, new remodel!

Grand on Grant

1 Block from Butler St ★ Patio ★ Dog Friendly!

2 beds/1.5 bath Hygge-Hus, Minute to Cafes & Shops

Steel City Retreat- 2 Bedroom house with Parking

Mid-century modern Lustron & Japanese garden

Quaint City Escape! ⦁ Parking ⦁ Long-term ⦁ Yard

East End Gem | Your Home Away from Home
Private house rentals

Private Hot Tub | King Bd | Workspace | Kids Okay!

2600 sq ft | 3 king beds | Rooftop Deck w Views

King Bed, Artist's Flat

Avant-Garde Escape by Walnut

Lawrenceville Gem:2 Kings & Yard

Cozy 2BR House in Pittsburgh

BRAND NEW, Private Parking, Stylish 3bedroom house

Upscale spacious kid-friendly home, amazing views!
When is the best time to visit Shadyside?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $122 NZD | $122 NZD | $122 NZD | $154 NZD | $150 NZD | $133 NZD | $128 NZD | $122 NZD | $122 NZD | $141 NZD | $140 NZD | $131 NZD |
| 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 house rentals in Shadyside

Total holiday rentals
Explore 100 holiday rentals in Shadyside

Nightly prices starting at
Shadyside holiday rentals start at $52 NZD per night before taxes and fees

Verified guest reviews
Over 4,930 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wi-Fi availability
100 of Shadyside holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Shadyside rentals

4.8 Average rating
Shadyside stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Rentals with an EV charger Shadyside
- Apartment rentals Shadyside
- Pet-friendly rentals Shadyside
- Rentals with outdoor seating Shadyside
- Fitness-friendly rentals Shadyside
- Family-friendly rentals Shadyside
- Rentals with a patio Shadyside
- Rentals with a washing machine and dryer Shadyside
- Rentals with a fireplace Shadyside
- House rentals Pittsburgh
- House rentals Allegheny County
- House rentals Pennsylvania
- House rentals United States
- 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
- Senator John Heinz History Center
- Children's Museum of Pittsburgh
- Bella Terra Vineyards
- Laurel Mountain Ski Resort
- Randyland




