Places to stay in Shadyside, Pittsburgh

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Top-rated places to stay in Shadyside, Pittsburgh

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

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Top guest favorite

A spacious common area showcases a large stone-topped kitchen island with six bar stools. Shelves display decorative items and plants. The seating area features a plush brown couch and an assortment of pillows. Large windows allow natural light, enhancing the modern, welcoming vibe.

Apartment in Shadyside

5 out of 5 average rating, 38 reviews

GYM+HULU+Parking Near Universities|Shopping|UPMC

Discover comfort and convenience in our charming city haven. Perfect for professionals and travelers, our apartment is your gateway to nearby dining, boutique stores, shopping outlets, & attractions. Building amenities include: 🚗FREE Street Parking for 1 Car(Based on Availability) 🏋🏻‍♂️State-Of-The-Art (24/7)Fitness Center 💼Private & Co-Working Spaces 🔌Level 2 EV Charging Station Available 🍵Complimentary Tea/Coffee Station 🏓Ping Pong Table, Comfy Seating Area 🍖Outdoor BBQ 🐾Pet Friendly

Guest favorite

An expansive outdoor deck features a sectional seating area with soft cushions, a coffee table, and a dining set. A fire pit with adjacent seating is visible, along with a patio heater. Potted plants add greenery to the space, enhancing the tranquil atmosphere.

Apartment in South Side Flats

5 out of 5 average rating, 8 reviews

Wow! Skyline Sunset Escape On Hackstown

Ahoj and welcome to your elegant 2-bed, 1.5-bath home with breathtaking downtown views! Newly renovated with a thoughtfully designed interior, this home offers a distinctive experience. Enjoy parking in a 2-car garage plus an outdoor space, and easy access to downtown and Oakland. Featured on the South Side Historic Homes Tour, it’s a true Pittsburgh gem. Pets are allowed! Relax on the deck with a fire pit, or unwind by the custom mosaic fireplace with a 55” TV or in the luxurious soaking tub.

Superhost

A spacious bedroom features a comfortable bed with white linens and a wooden dresser. A large mounted TV is visible above the dresser. The room boasts a brick accent wall and a ceiling fan, providing a modern touch to the inviting space.

Home in Mount Washington

4.85 out of 5 average rating, 13 reviews

The Colorful Abode with Deck in Mt Washington

Hi! We are Grace and Chibi! Welcome to our charming and unique home, where you can experience living in style! The house is located in the vibrant Mt Washington neighborhood with numerous restaurants, cafes and views to explore. This colorful and bright house boasts of an amazing outside deck, perfect for enjoying your morning coffee or a glass of wine in the evening. This house is an ideal vacation home for families, couples, or friends. Book now and experience the best of living in style!

Guest favorite

Home in Pittsburgh

4.94 out of 5 average rating, 164 reviews

Huge 6 BDRM min to Downtown & Stadiums w/ parking

Gather with friends and family in our renovated Pittsburgh home, designed for comfort and fun! ✅ 6 Large Bedrooms & 3 Full Baths – Includes a soaking tub ✅ Easy Parking – Two-car driveway + plenty of free street parking ✅ Stocked Kitchen – Fully equipped with essentials ✅ Spacious Living Areas – Two living rooms for lounging ✅ Entertainment – Projector & sound system for movie nights ✅ Family & Pet-Friendly – Room for everyone ✅ Cozy Fireplace – Available Nov.–Feb. Everyone will enjoy it!

Guest favorite

A sweeping view captures the bustling PNC Park, with a vibrant green playing field framed by cheering fans. The scenic Pittsburgh skyline rises in the background, showcasing diverse architectural styles under a clear blue sky adorned with fluffy clouds.

Apartment in Pittsburgh

4.95 out of 5 average rating, 119 reviews

Walk to Pnc+Acrisure!2BR w/ KING bed-FREE parking!

Watch the sun shine through two story stained glass windows in our recently restored 1800’s church turned luxury apartment! Featuring an open, two story floor plan with two large bedrooms, two full bathrooms, a fully stocked kitchen and organic coffee bar plus more located on a quiet, residential street in one of Pittsburgh’s most up and coming neighborhoods. Walk a few blocks to Allegheny General hospital as well as neighborhood bars plus all major stadiums. This spacious condo has it all!

Guest favorite

An exterior view of the home is presented amidst vibrant autumn foliage. The multi-story structure is surrounded by trees showcasing various warm colors, complementing the peaceful nature setting. Large balconies offer views of the surrounding landscape, enhancing the serene atmosphere.

Apartment in Pittsburgh

4.98 out of 5 average rating, 120 reviews

Amazing views! Free Parking!

After a year-long restoration project, we are thrilled to present our home in Pittsburgh's historic north side. What awaits you is a quiet, downtown gem surrounded by nature with amazing city views. What You'll Love: -Total and complete renovation between 2020-2021 -Gourmet, fully-equipped kitchen including coffee/tea station -Remarkable city views -Close to stadiums, downtown, museums -Relaxing patio -Gigabit internet connection -Peaceful nature surroundings -Comfortable memory foam beds

Top guest favorite

A comfortable living area features a dark leather sofa and an accent chair with a geometric pattern. Light spills in from a doorway leading to the dining area, where a wooden table is set for four. Decorative elements include a coffee table and wall art.

Home in Pittsburgh

4.97 out of 5 average rating, 397 reviews

Head to Pittsburgh From Mt. Lebanon Cottage

Mt. Lebanon Cottage is a craftsman-style home that fuses contemporary styles with traditional elements. Enjoy our well-equipped kitchen, enjoy a coffee for two on the deck nestled in the trees or unwind on the front porch and enjoy the friendly neighborhood vibe. The home is in a walkable neighborhood of tree-lined streets and friendly locals. Blocks from unique shopping boutique options and dine at tasty local restaurants. Hike in the nearby nature and visit Pittsburgh just minutes away.

Guest favorite

The dining area features a wooden table set for six, surrounded by matching chairs. A decorative area rug lies beneath the table. In the adjacent living space, a sofa and a chair invite relaxation, with large windows providing natural light.

Home in South Side Flats

4.95 out of 5 average rating, 91 reviews

Cozy, Pet-Friendly Home in Pittsburgh South Side

Welcome to Steel City! Our updated two-bedroom house in the lively South Side is a perfect home for your group to relax and unwind including your four-footed friends! After exploring the city, enjoy the mood lighting on our cozy patio or check out the local restaurants and bars within walking distance. Work from home with a desk space in each bedroom. Our home has everything you will need and a perfect location if you're looking to have a truly authentic Pittsburgh experience!

Guest favorite

Apartment in Pittsburgh

4.96 out of 5 average rating, 174 reviews

Free Parking★ Walk Everywhere ★North Side Gem!

You'll walk in and say wow! Our place has exposed brick throughout, a generous open floor plan, soaring ceilings, a spacious bathroom and two cozy bedrooms - king & queen 12" thick mattresses. Work from home at your desk, whip up a cocktail or meal in the full kitchen, or lounge on the couches and watch a movie or browse the web (1 Gbps). It's a short walk to Allegheny General and a few minutes to the bars & restaurants and stadiums on the North Shore - it's a great location!

Guest favorite

A staircase with a wooden banister ascends from the main floor, flanked by exposed brick walls. The space transitions into an open dining area, featuring a dark wooden table with multiple chairs. Warm lighting highlights the hardwood flooring and modern kitchen in the background.

Home in Pittsburgh

4.99 out of 5 average rating, 147 reviews

The Larrybird Inn - Steps from Butler Street!

The Larrybird Inn is situated in the heart of Lawrenceville, in a beautifully restored home over 100 years old. Park your car for the weekend and enjoy the neighborhood and other surrounding areas by foot or bike. Walk to nearby bars, restaurants, see a movie all within hundreds of feet away! There is also Arsenal bowling lanes across the street! We invite you to stay in our home, one of the most charming Airbnbs in Lawrenceville.

Guest favorite

An expansive common area is shown featuring a billiards table at its center. Surrounding spaces include stylish seating arrangements, built-in shelves displaying decor, and a range of windows allowing natural light to brighten the wooden floors.

Apartment in Pittsburgh

4.89 out of 5 average rating, 140 reviews

Luxury Apartment with Balcony Near Stadium

You can stop your search now. You just found the perfect place to book for your trip to Pittsburgh. Pet Friendly with pet wash in building :) Clean. Trendy. Quick host responses. Get the good nights' sleep you deserve with our dreamy Queen bed. Spend your morning or nights in peace with a beautiful view. If you're on a business trip, skip a hotel or other boring Airbnb's for your extended stay and book now with us.

Superhost

A charming entryway features a combination of rustic wood accents and modern decor. A clear plastic chair is positioned beside a vintage dresser. Floral arrangements are displayed on the dresser, while light is filtered through a sheer curtain, illuminating the space.

Apartment in Bloomfield

4.74 out of 5 average rating, 31 reviews

Lovely Private Bloomfield Apt Amazing King Bed

Adorable 1st floor apt on a quiet residential street a block from West Penn Hospital and a short walk to everything. A minute from the Bloomfield business district lined with restaurants, coffee, & bakeries. World-class parks and a number of grocery stores -Whole Foods, Target + locally owned brews & pubs are here. Free street parking that’s always available out front. Easy access to CMU & Pitt.