Vacation rentals in North Side

Cultural District new King Suite whirlpool tub

Experience Pittsburgh's Cultural District from this new king suite! You are surrounded by Pittsburgh's best restaurants, shops, steps away from the Convention Center, theaters, and more. Designed for comfort and convenience in an unbeatable location. - King bed - Whirlpool tub / shower - Equipped Kitchen & Laundry - Walk to everything - Mult garages within 5 min - 24/7 guest support Perfect for business trips, events, or weekend getaways. We're here for you before, during and after your stay!

*Sleeps 9! Dogs are fine! Huge historic charmer!*

If you love a "REAL HOME" this historic beauty is full of CHARM! You can literally feel the history as you walk across the occasional creaky floor board. Stunning brick, open beams in family room. Located in one of the coolest areas in Pittsburgh, most attractions are walking distance. Museums, restaurants, sport venues. The Aviary, Allegheny Commons Park & Lake Elizabeth are just one block away! Perfect for families, friends, groups & Fido, so don't be surprised if you find a dog hair or two.

King Bed Carriage House in Mexican War Streets

Welcome to your bright & colorful carriage house, located right in the heart of the Mexican War Streets! With lots of space for a couple or solo traveler, it has everything you need for a short or long stay. Featuring a lovely king bed, well-stocked kitchen, work-from-home desk, spacious dining area, colorful & comfortable living room, and loads more! Parking is free with our permit, but if you don't have a car, you're perfectly situated to walk to some of the best of the burgh nearby!

Deutschtown Carriage House

Newly renovated carriage house in the heart of the historic Deutschtown district. This special place is close to everything: PNC Park, Acrisure Stadium, Allegheny General Hospital (AGH), National Aviary, Children’s Museum, the Warhol, Mattress Factory, Allegheny Commons Park, Stage AE, Downtown, and many restaurants. Whether you're a sports fan, a traveling nurse, a concert-goer, or just coming to Pittsburgh for a little of everything, this is the place for you.

Two King Beds★ Beautiful Custom Space ★ Walkable!

Stay at our North Side row home, with an incredible open floor plan, large deck, spacious bathroom, two large bedrooms with king beds, and stocked kitchen on a quiet street! It's a short walk to Allegheny General and a few minutes to the bars & restaurants and stadiums on the North Shore. With way more amenities than a hotel, whip up a cocktail or meal in the full kitchen and relax on the lounge couch and watch TV or work from home with high speed internet.

KING Bed • Modern City View Escape • Free Parking

Welcome to our stunning, fully renovated Place! This modern gem features a spacious open-concept layout, thoughtfully designed with a stylish wood slats that elegantly divides the living areas and the bedroom while maintaining an airy, seamless flow. Every detail has been meticulously updated, offering a fresh, contemporary vibe with top-notch amenities. Perfect for those seeking a chic, open living experience in a beautifully reimagined space!

3bd/3b Home Rich in History+Design+comfort

An architecturally unusual pair of post civil war row houses have been artistically combined to highlight their past and provide all the modern conveniences one needs . The combination of the beam and brick infill construction is juxtaposed with white walls and vintage 20th century design classics. Located directly across from the widows home built after the civil war, this area is one of Pittsburgh's most significant historical neighborhoods.

Exposed Beams, Modern Vintage War Streets Charmer!

✨ Discover the charm of Pittsburgh’s historic Mexican War Streets! This stylish 2BD/1BA home combines exposed brick, rich wood tones, and modern comforts for a warm, inviting stay. ☕ Enjoy locally roasted coffee, lounge on the cozy sectional, or catch up on work before heading out. With PNC Park, Acrisure Stadium, the Warhol Museum, and top dining just minutes away, you’ll love exploring this highly walkable neighborhood! 🚶‍♂️🏙️

Walk to Acrisure! Free Private Park | Sleeps 8

✨ A hidden gem in Pittsburgh’s Historic North Side! This vibrant home offers unbeatable walkability—minutes to Acrisure Stadium (1 mi), PNC Park, Andy Warhol Museum, and Randyland. Stroll to Penn Brewery for Oktoberfest, plus coffee shops, pubs, and restaurants. Downtown, Rivers Casino, and the Strip District are also walkable. Includes a free private parking spot—perfect for exploring all Pittsburgh has to offer!

Modern Victorian Apartment - Quiet but walkable!

This 3rd floor apartment is located in the heart of the Northside in Mexican War streets. It’s freshly renovated with a massive kitchen and living room/dining room. A block away from Commonplace Coffee and under 15 minute walk to just about everything, including Pirates, Steelers, Aviary, children’s museum, Federal Street, Western Ave and more! We love this neighborhood and you’ll love it too!

Private Roof Deck with Cliff-Side Skyline Views

Escape to this architect-designed, 2-bedroom cliff-side apartment with breathtaking panoramic views of the Pittsburgh skyline and three rivers. This private, two-floor retreat comfortably fits 4 guests and features a stunning roof deck and dedicated workspace. Enjoy a peaceful hillside setting just minutes from the city's vibrant culture and dining. Free on-street parking is hassle-free!

Dual Rooftop Decks with Skyline Views & Firepit

This modern 4-bedroom downtown Pittsburgh home features two private rooftop decks with skyline views and a fire pit, plus a fully automated smart home system with whole-home Bluetooth sound. Walk to cultural attractions and restaurants, or work remotely with dedicated ergonomic workspaces and fast wifi. Ideal for groups, families, or remote workers seeking space and downtown access.