Townhome holiday rentals in Squirrel Hill

A modern living area features a gray sofa adorned with black accent pillows. A black console table is present near the wall, while a dark area rug covers the light wood flooring. Natural light enters through a small window, complemented by recessed lighting overhead.

4.97 out of 5 average rating, 174 reviews

Modern Rowhouse in Trendy, Walkable neighborhood!

This 2 bedroom 1 bath row house was built in 1900 and underwent a total gut renovation recently. Located just 2 blocks from Butler street in one of the best locations in Pittsburgh. Lawrenceville is named one of America’s coolest neighborhoods. There are so many top notch restaurants, bars, boutiques and galleries to choose from, all within walking distance. I would be happy to provide suggestions for some of my favorite places to go in the neighborhood. Close to the strip and downtown too!

A spacious living area features large windows that allow natural light to brighten the room. A patterned sofa is paired with a contemporary armchair, while a wooden coffee table rests on a decorative area rug. A striking mural of trees adorns one wall.

4.97 out of 5 average rating, 171 reviews

The Paris of Appalachia— FREE parking

Centrally-located in park-like, tranquil, historic area. Easy, quick walk to PNC Park, Acrisure Stadium, Stage AE, The Warhol, Science Center, North Shore, & AGH Hospital (all 5-7 min walk). Downtown is a 15 min walk or short lightrail. The Strip, Lawrenceville, Sq. Hill & U. Pitt/CMU all a short drive. Newly renovated, artful space (1100+ sq.ft) in one of Pittsburgh's most desirable city neighborhoods. WiFi, 65' smart TV, & FREE parking permit (nearby hotels charge $45/night for parking).

The exterior of the townhouse features warm-toned brick walls with traditional window accents. A welcoming front porch is highlighted by a red door and two chairs. Lush green grass and blooming yellow flowers provide a vibrant contrast against the brick facade.

4.96 out of 5 average rating, 108 reviews

Minimalist Townhouse with Stunning Skyline View

This townhouse is a gem in Pittsburgh! Located on a quiet street in Greenfield, it is central to everything the city has to offer. Situated on top of a hill, the skyline can be seen from the deck, and it’s breathtaking with a sunset! Walkable to Squirrel hill, less than 10 minutes driving from downtown, Shadyside, Oakland. The cohost has lived in Pittsburgh for 6 years and would be delighted to offer recommendations around the city. Meticulous cleaning standards are followed for your safety.

The primary bedroom features a spacious queen bed with a plush blanket and decorative pillows. A modern staircase leads to the loft office area above. Natural light fills the room, complemented by artwork on the walls and a soft rug underfoot.

4.97 out of 5 average rating, 211 reviews

King Bed | Amazing Location | Stunning Design

✨Modern Nordic charm in the heart of Lawrenceville!✨ Just two blocks from Butler Street, you’ll be surrounded by Pittsburgh’s best bars, restaurants, coffee shops, & patios. This art-filled 2BR home combines thoughtful design with high-speed internet, two 55” 4K TVs, and a cozy loft office. Cook in the fully stocked kitchen, stream your favorites, or unwind in a space that’s as functional as it is stylish. Recently remodeled with comfort in mind—it’s the perfect home base for work or play!

The living room showcases a modern grey sectional sofa adorned with decorative pillows. A round wooden coffee table sits on a textured rug, complemented by a glass side table featuring a small plant. Natural light filters through a window beside the seating area.

4.84 out of 5 average rating, 138 reviews

Renovated Brownstone – Ideal Location for Families

Experience Pittsburgh together in our spacious townhouse, nestled in the historic and walkable Manchester neighborhood. Your family's adventure begins just steps from downtown, ad the stadiums, making this the ideal Pittsburgh base. Kids and parents will appreciate the playground and walking trails nearby. More than just a place to stay, our townhouse is your launchpad to the city's vibrant energy. Enjoy comfort, convenience, and the perfect location for your group's Pittsburgh experience.

A modern kitchen features wooden cabinetry and stainless steel appliances, including a refrigerator and gas stove. A granite countertop complements the space, while a metallic light fixture illuminates the area. A nearby staircase leads to the upper level of the home.

4.94 out of 5 average rating, 358 reviews

Charming Home • Vibrant Neighborhood

Experience the best of both worlds in Pittsburgh's historic South Side: a peaceful retreat just moments from the city's vibrant energy. Enjoy a quiet night's rest and then step out to explore the South Side's renowned shops, restaurants, and nightlife. With easy access to Pittsburgh's major attractions, you can effortlessly discover all the city has to offer. Our professionally managed home provides a spacious and impeccably clean haven for groups, complete with complimentary parking.

A well-lit living area features a modern gray sofa adorned with yellow accent pillows. A decorative wall mirror with circular frames reflects soft light from a nearby lamp. Natural light enters through a partially draped window, creating a welcoming ambiance.

4.95 out of 5 average rating, 116 reviews

THE STRIP DISTRICT ** NEWLY RENOVATED ROW-HOUSE**

Built in 1890 in the Historic Strip District this newly gut renovated townhouse is located in the best and most central area in Pittsburgh. Gorgeous modern appliances and furniture welcome guest in this 2 bedroom 1.5 bathroom, with a fully finished basement as well as a private and gated backyard. The renovations were done with exquisite attention to detail and furnished with a MODERN flair. We are located minutes from Downtown and Lawrenceville. Welcome to your home away from home.

The living room features bold teal walls and large windows, allowing natural light to fill the space. A comfortable gray sofa is adorned with decorative pillows, complemented by a gold coffee table atop a textured black rug. Stylish curtains frame the windows, enhancing the inviting atmosphere.

4.85 out of 5 average rating, 274 reviews

Colorful Southside gem! Off-street parking!

Great 2 story, 2 bedrooms apt located just a few blocks up from the South Works! Tons of shopping, restaurants, bars & coffee shops nearby! The space is bright, colorful & travel-themed. Fully outfitted for short or long term rentals, with plenty of charm & style to make you feel right at home. 2 bedrooms feature 1 King, 1 Full & living room has 1 sofa that lays flat as a twin-sized bed, sleeping 5 comfortably! Eat-in kitchen has new appliances & seating for 4! Ideal location!

The bedroom features a spacious bed adorned with a decorative comforter, complemented by bedside lamps and a stylish mirror above a small dresser. Light-colored walls and wood flooring enhance the room's bright, inviting ambiance.

4.93 out of 5 average rating, 189 reviews

King Bed★ Off Street Parking!★ Pet Friendly

Book confidently with a SuperHost! Free off-street parking in a private driveway is included! Modern style and great amenities abound in this one bedroom second floor duplex property on the North Side. The space is set apart from others by a host of amenities - well-stocked kitchen, cozy linens, 400mpbs internet, 55" HDTV, whole bean coffee, a stocked kitchen, and more! It's close to stadiums, bars, restaurants, and breweries of the North Shore, and AGH is across the street.

A welcoming living area features a rustic brick fireplace and a mounted flat-screen television. Two stylish brown chairs are positioned beside a black coffee table, while a dining space is visible in the background, complete with a modern kitchen layout.

4.79 out of 5 average rating, 204 reviews

Homey & Perfectly Located 3BR/2BT - Sleeps 8!

Comfortable, homey and welcoming - Our peaceful and centrally-located property is wonderful for small groups. Open concept living + amenities like a game room to help you rest, relax, and unwind. 3 bedrooms/4 beds + 2 full bathrooms to comfortably sleep 8! South Side location just a short distance to all attractions Pittsburgh has to offer, yet quiet in the evenings. Wonderful property for traveling business partners who want space, family getaways, and small group travelers.

A winter cityscape showcases a view of downtown buildings against a clear blue sky. Snow blankets rooftops, creating a contrasting texture with the urban landscape. The skyline is composed of high-rise structures, highlighting the city's architecture.

4.99 out of 5 average rating, 169 reviews

Small house in a big world

100+ year old house always pertained to same family. The owners trusted we would continue caring for the little house, and so we do. We fell for the view, for the history, for the dreams the house once hosted, and think the little house has vast room for other dreams that go to the horizon, a wonderland. We are proud of being a part of the come back of the neighborhood, and thank our neighbors for their magnificent friendship, and God for blessing the encounters to come.

A cozy seating area is highlighted by a mid-century wooden console with a flat-screen television mounted above. A gray sofa and a cream-colored armchair with red accents provide comfortable seating. Nearby, a wooden coffee table displays magazines, while a colorful area rug adds warmth to the space.