
House holiday rentals in Shadyside
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Top-rated house rentals in Shadyside
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*z 2231 1BR Southside *Sloped* Home Close to Pgh
Quirky South Side Slopes home convenient to Pittsburgh and all local attractions. This property is located in one of Pittsburgh's original industrial neighborhoods which is remaking itself into a fun vibrant community. With fun views from high above the city this neighborhood was home to many Pittsburghers who worked in the steel mills that helped build our great nation. Come get a feel for the way Pittsburghers used to live and enjoy everything Pittsburgh has to offer today, yinzer approved!

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 1BR Retreat | Near Downtown & Airport
Welcome to your perfect Pittsburgh home away from home! 🏡 This spacious, light-filled 1-bedroom unit is ideal for solo travelers, couples, or small groups. With high ceilings, a large bathroom, full eat-in kitchen, and cozy front porch, you'll feel right at home. 🌞 📍 Located in walkable Crafton, just minutes from downtown, Station Square, and the North Shore — and only 13 miles from the airport. Whether you’re here for work or fun, this charming space is the perfect base for your stay!

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.

Upscale Modern 2 BR Apartment
This spacious, newly renovated, fully equipped and private access apartment was built for your enjoyment! The granite counter tops and porcelain tiled shower are a hint of the luxuries throughout. You can park on the property or on the street. Located in the heart of Squirrel Hill, right near Schenley park, the Squirrel Hill business district and bus lines. Easy Access to Bakery Square, Shadyside, Waterfront, Downtown, Museums & Galleries, Universities, hospitals, and all Sports venues.

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.

3-Story Historic Home | Steam Shower | 3 King Beds
Welcome to our charming 3-story home! This home is huge with 5 BRs and 3.5 bathrooms, perfectly located in the heart of Shadyside within a short walk of plenty of restaurants, coffee shops, bars, shops, and more! 🌟 5 beds with memory foam mattresses (3 King / 2 Queen) 🌟 Steam shower in Master Bedroom 🌟 2 rollaway beds + 1 crib 🌟 Washer/ dryer in-unit 🌟 2 car garage (Free, tight fit) 🌟 Pet friendly My team and I are here for you 24/7 before, during and after your stay with us!

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).
Popular amenities for house rentals in Shadyside
House rentals with a pool

Posh Pittsburgh ~ 2-story luxury suite & patio

Oasis on the edge

A beautiful cozy home away from home!

Convenient townhome

Renovated Cozy Duplex w/pool, Close to downtown

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

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

Cozy 2BR House in Pittsburgh

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

PBR - Pittsburgh Bloomfield Rowhouse

Steel City Retreat- 2 Bedroom house with Parking

Skyline Views ★ Stunning Balconies ★ Luxe Home!

Mid-century modern Lustron & Japanese garden

Quaint City Escape! ⦁ Parking ⦁ Long-term ⦁ Yard
Private house rentals

Foxy home, off-street parking, new remodel!

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

Dedicated Parking | 2 King Beds | Arcade | BBQ

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 | $91 SGD | $91 SGD | $91 SGD | $114 SGD | $112 SGD | $99 SGD | $95 SGD | $91 SGD | $91 SGD | $105 SGD | $104 SGD | $98 SGD |
| 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 $39 SGD 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wifi availability
100 of Shadyside holiday rentals include wifi 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!
Destinations to explore
- Family-friendly rentals Shadyside
- Rentals with an EV charger Shadyside
- Pet-friendly rentals Shadyside
- Flat rentals Shadyside
- Rentals with outdoor seating Shadyside
- Fitness-friendly rentals Shadyside
- Rentals with a fireplace Shadyside
- Rentals with a washing machine and dryer Shadyside
- Rentals with a patio Shadyside
- House rentals Pittsburgh
- House rentals Allegheny County
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- 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




