Townhouse 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, 175 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!

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.

Superhost

A welcoming living area is present, featuring a spacious sectional sofa positioned in front of a large flat-screen television. Natural light filters through the window, which is adorned with sheer curtains. A wooden accent wall complements the vibrant red walls, creating a cozy ambiance.

4.81 out of 5 average rating, 324 reviews

TripH - townhouse, EV charger, off street parking

What was once my starter home, is now available for you to enjoy! Whether you’re on a family trip, a group get-a-way, or just a couple looking for a place on your adventures, TripH has you covered. Lots to do in the house and right in the middle of all the fun of Pittsburgh, so everything is close. Check out the listing across the parking lot: http://airbnb.com/h/tripD and the listing to book them both and save on fees http://airbnb.com/h/trippgh Grocery store, police, and ymca close by!

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, 212 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!

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!

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.

An inviting private hot tub is situated in a fenced backyard area, surrounded by soft lighting and decorative plants. The brick wall of the house provides a rustic backdrop, creating a cozy ambiance at dusk.

4.92 out of 5 average rating, 374 reviews

Hot Tub, King Bed, Cabin Vibes in Lawrenceville!

With cozy cabin vibes, exposed brick, and designer touches, this romantic getaway is perfect for couples or a relaxing stay. Escape to a rustic-modern retreat in the heart of Lawrenceville, just one block from Butler Street! Unwind in the private hot tub, snuggle up on the couch by the fireplace, or explore the city's best dining and nightlife just steps away. Completely remodeled in January 2025 with luxe amenities—book now for an unforgettable stay!

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.

4.99 out of 5 average rating, 142 reviews

Retro Rowhouse, Corner Little House, Lawrenceville

Looking for a fun getaway weekend in Pittsburgh ? This unique triangular row house in Lawrenceville with mid century decor and cozy urban patio is an easy walk to to great restaurants and shops on Butler St. and Penn Ave. and to Children's Hospital . Also close to the Strip District and downtown Pittsburgh. The row house is a warm, intimate space for singles or couples . Also 10 minute drive to Point Park and 2026 NFL Draft April 23-26!

A spacious bedroom features a textured brick accent wall, a comfortable bed with a patterned coverlet, and two bedside lamps. A vintage dresser and a decorative painting add character, while natural light illuminates the hardwood floor, enhancing the inviting atmosphere.

4.9 out of 5 average rating, 368 reviews

Charming Getaway: Off-Street Parking, Walkable

Live like a local in this completely updated row house located just a 10 minute walk from 2 of the Pittsburgh's hottest neighborhoods, Lawrenceville and the Strip District. Free off-street parking is a bonus. Inside you'll find an updated kitchen, a cozy couch, 1 gig internet, three smart TVs, a collection of original artwork. Enjoy free off-street parking available for guests. Plus lightning fast WiFi & a dedicated workspace.

A fenced-in yard features a fire pit surrounded by mulch, creating a cozy outdoor space. A covered patio with a dining set is visible, illuminated by string lights overhead, adding to the inviting atmosphere for gatherings.