House vacation rentals in Shadyside

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Top-rated house rentals in Shadyside

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Top guest favorite
A functional kitchen features grey cabinets complemented by wooden countertops. Open shelves display various glassware and kitchen essentials. A large sink with a dish drying rack is visible, alongside modern appliances, including a stainless steel refrigerator and coffee maker. Natural light enters through a window with blinds.
Home in North Side
4.93 out of 5 average rating, 212 reviews

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.

Top guest favorite
The exterior showcases a charming three-story home with a distinctive architectural design. Its light-colored brick facade is accented by purple trim. Lush green foliage surrounds the entrance, which features steps leading up to a welcoming porch with colorful potted flowers.
Home in Friendship
4.98 out of 5 average rating, 121 reviews

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.

Superhost
A living room features comfortable seating, including a dark leather couch and a vintage blue chair. Shelves line the walls, displaying decor and plants. A warm rug sits on the wooden floor, complemented by natural light filtering through sheer curtains.
Home in Garfield
4.91 out of 5 average rating, 132 reviews

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.

Top guest favorite
The kitchen area features dark wood cabinetry with a granite countertop. Stainless steel appliances, including a microwave and refrigerator, are neatly installed. A tiled backsplash in a soft grey hue complements the modern design. A small dining table with two chairs occupies the space.
Home in Squirrel Hill South
4.93 out of 5 average rating, 338 reviews

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.

Guest favorite
A two-story house features a light-colored exterior with dark shutters. A covered front porch with seating arrangements is visible. The property is bordered by a black fence and surrounded by trees, while neighboring colorful homes add to the neighborhood's charm.
Home in Shadyside
4.89 out of 5 average rating, 183 reviews

3 BR home|Steps from Walnut Street w/Free parking!

3 Bed / 2 Bath home in the heart of Shadyside! This home is located steps away from popular Walnut Street, which has plenty of fun restaurants, shops and more! 💫Four memory foam beds (2 king/ 2 queen) 🌟King bed w/ Full bathroom on First Floor (No Stairs) 💫Twin-sized rollaway bed + Pack n Play Crib 💫Off street parking 💫Private front and back patio 💫Free in-unit washer/ dryer 💫Fully stocked kitchen My team and I are here for you 24/7 before, during and after your stay with us!

Top guest favorite
The bedroom features a spacious bed with white bedding and multiple patterned throw pillows. Natural light filters through the large windows, enhancing the warm wooden floors. A decorative wall separates the bedroom from the living area, while shelves provide additional storage.
Home in Bloomfield
4.92 out of 5 average rating, 209 reviews

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.

Guest favorite
A bright bedroom features a spacious bed adorned with a patterned throw and decorative pillows. Soft lighting from two bedside lamps enhances the atmosphere. A large window with sheer curtains provides natural light, and a wall displays a friendly animal portrait complemented by hanging greenery.
Home in Troy Hill
4.96 out of 5 average rating, 131 reviews

The View*Sleeps 6* City Home

Kick back and relax in this calm, stylish space where you can take in the river views on the deck - or hang out in the tv lounge. A designated work area, conveniently on the main floor, doubles as extra sleeping space. With an easy drive to the stadiums, arena, downtown, the Theater district, the Strip district, the Childrens museum, the Science center, nature or city hikes, and just across the bridge from the Childrens hospital and Lawrenceville - you will feel right at home!

Guest favorite
A modern living area is highlighted by large windows allowing natural light to fill the space. A comfortable sofa is adorned with decorative pillows, facing a wooden coffee table. A tall lamp stands nearby, and shelves display various books and decor.
Home in East Carson Street
4.91 out of 5 average rating, 413 reviews

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).

Guest favorite
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 favorite
A colorful living space is highlighted by vibrant decor, including playful wall art and whimsical flowers. The seating area features a plush sofa and chairs, inviting relaxation. Bright LED lights add to the whimsical ambiance, while a staircase leads to the upper level.
Home in Central Lawrenceville
4.96 out of 5 average rating, 215 reviews

Willy Wonka Themed | King Bed | Free Parking | Arc

*As Seen on CBS News & the Pittsburgh Post-Gazette – The Ultimate Willy Wonka Experience!* Rank One Stays presents Pure Imagination - You’ll explore the world of Wonka complete with oversized gummy bears, lollipops, and a wondrous boat in a completely unique, interactive and immersive Wonka experience just minutes away from Acrisure, PNC Park, PPG Arena, and Downtown.

Top guest favorite
A charming entrance is framed by lush greenery and vibrant rose bushes in full bloom. The walkway leads to a welcoming door, surrounded by landscaped flower beds and shrubs, creating a serene and inviting atmosphere.
Home in East Liberty
4.98 out of 5 average rating, 400 reviews

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.

Top guest favorite
A comfortable living area is presented, featuring a sectional sofa with yellow accent pillows and a decorative wall art piece. A round wooden coffee table sits at the center, accompanied by a small indoor plant. Natural light filters through the partially opened window.
Home in Bloomfield
4.94 out of 5 average rating, 171 reviews

Charming Lawrenceville Rowhome

Enjoy a stay in our cozy and beautifully-renovated Pittsburgh row-home. Located in the heart of Central Lawrenceville, you will be just steps from UPMC Children’s Hospital and walking distance to dozens of bars, restaurants and boutique shops on Butler St. (~10 minutes), Liberty St. (~10 minutes), and Penn Ave. (~2 minutes).

Popular amenities for Shadyside house rentals

When is the best time to visit Shadyside?

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Avg. priceG$14,850 GYDG$14,850 GYDG$14,850 GYDG$18,615 GYDG$18,196 GYDG$16,105 GYDG$15,477 GYDG$14,850 GYDG$14,850 GYDG$17,151 GYDG$16,941 GYDG$15,896 GYD
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Quick stats about house rentals in Shadyside

  • Total vacation rentals

    Explore 100 vacation rentals in Shadyside

  • Nightly prices starting at

    Shadyside vacation rentals start at G$6,275 GYD per night before taxes and fees

  • Verified guest reviews

    Over 4,930 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wi-Fi availability

    100 of Shadyside vacation 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!

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