Holiday houses in Herrs Island

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Top-rated holiday rentals in Herrs Island

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Guest favourite
A modern living area is highlighted by a spacious orange sectional sofa and a wooden coffee table. Natural light is filtered through large windows, illuminating the warm wood flooring. A staircase leads to an upper level, complemented by decorative lamps and a neutral color palette.
Townhouse in Pittsburgh
4.86 out of 5 average rating, 7 reviews

Walk River Path to ‘26 NFL Draft *FREE Parking*

🏈 THE 2026 NFL DRAFT 🏈 Step out your front door onto Three Rivers Heritage Trail & walk to Acrisure Stadium!! Luxury 2200 sq ft 2-bed, 2.5-bath townhouse on the Allegheny River island of Washington's Landing. Water views. Parklike, modern, spacious, well-equipped, and close to downtown Pittsburgh. Walk or bike to the Strip District and beyond. Two outdoor decks. 10 new pickleball courts on the island. Stroll past the boat docks to Redfin Blues (in spring & summer) for happy hour or a boat ride

Top Guest favourite
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 Pittsburgh
4.94 out of 5 average rating, 227 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.

Superhost
A dining area features a wooden table surrounded by four chairs, illuminated by natural light from two windows. A clock and a piece of wall art enhance the space's decor, while a doorway leads to a bedroom area, complementing the home’s inviting atmosphere.
Apartment in Pittsburgh
4.83 out of 5 average rating, 46 reviews

Pittsburgh Modern & Cozy 2Bdrm With Free Parking

Peaceful and family oriented Two Bedroom apartment with a central location in Pittsburgh. 7 mins from Downtown, NHL and NFL games, Lawrenceville Strip District. Enjoy the proximity to shopping, bars & restaurants. This apartment features 2 bedroom, 1 bathroom on the on the lower floor of a family house. Stylishly setup, our home features high speed internet and Smart Home Security system for additional safety of our guests. This place is suitable for families only and this is NOT a party place.

Top Guest favourite
The game room features a combination table for dining, ping pong, and pool. An electric fireplace and a golden tee arcade game add warmth and entertainment. Natural light enters through large windows adorned with curtains, while a vibrant mural decorates one wall, enhancing the lively atmosphere.
Home in Pittsburgh
5 out of 5 average rating, 72 reviews

Spacious 4BR | 2 Kings, Firepit, Arcade + Parking

Enjoy this stylish, comfy, and fully renovated gem in Troy Hill, minutes from North Shore, Downtown, Strip District, and more. The home features an off-street parking pad, free street parking, and a private backyard with a firepit, grill, and Adirondack chairs. Inside, the living room converts into a movie theater, and the dining room into a game room. Two of the four bedrooms boast king-sized beds. Each bedroom has a Roku TV with guest mode. There are two full-length mirrors for getting ready.

Guest favourite
The open-concept living space features a modern kitchen with stainless steel appliances and exposed brick walls. A plush couch faces a wall-mounted Smart TV, while a shuffleboard table and decorative plants add character to the inviting atmosphere.
Home in Pittsburgh
4.89 out of 5 average rating, 28 reviews

King Suite w/ View | Off Street Parking | Deck

Modern 1BR Skyline Retreat | Deck • Off Street Parking Discover this stylish 1 bed suite in Troy Hill with skyline views—ideal for couples, solo adventurers, and business travelers. ✔️ King bed w/ premium bedding ✔️ Private deck overlooking the Pittsburgh skyline ✔️ Full kitchen + stocked coffee & espresso bar ✔️ Fast Wi-Fi w/ dedicated work space ✔️ In-unit washer & dryer ✔️ Free off-street parking ✔️ Quick drive to stadiums, Downtown Pittsburgh, Strip District, Pitt/CMU, & Lawrenceville

Top Guest favourite
A well-lit corner showcases a small wooden table with two chairs next to a window. A geometric mirror is mounted on the wall above potted plants. A sleek microwave is visible, and a wall-mounted television adds functionality to the cozy space.
Guest suite in Pittsburgh
4.98 out of 5 average rating, 503 reviews

Walkable Lawrenceville, Designer “Tiny Living”

The Nesting Box is an ideal space to return to and recharge in after “free-ranging” locally. Comfortable, cool, and centrally located to the best of Butler Street. Designers collaborated to maximize the minimal space with creative comforts for experiencing "tiny living". Our shipping container addition led us to have 2 front 🚪. We welcome guests to our on-street private guest suite. Urban family homestead with 1 🐈‍⬛, 2 🐕, and 3 🐓 that resided with us for 5 years (recently rehomed to farm).

Top Guest favourite
The living area features a blue three-seater couch with a round rug underneath, paired with a coffee table. A kitchen island with bar stools is visible in the background, while a dining table and wooden stairs leading to an upper level are seen on the right. Natural light enters through nearby windows.
Apartment in Pittsburgh
4.94 out of 5 average rating, 234 reviews

Brand New! Lawrenceville KING Suite - Huge Balcony

1 bedroom 1 bath apartment w/ a HUGE private balcony steps from Butler St in Lawrenceville neighborhood! Sleeper Sofa and extra linens for bigger groups. BRAND NEW construction! Enjoy this stylish space in the coolest neighborhood in town, steps to dozens of restaurants, shops, coffee shops. A few blocks to UPMC Children's hospital and the Strip District, short drive to Downtown, North Shore, Shadyside, Oakland, very close to Pitt, CMU, & several hospitals! Book your stay today!

Superhost
A historic hillside duplex is depicted, featuring a blend of grey and blue siding. Multiple windows are present, allowing ample natural light. The entrance is marked by a bold red door, complemented by black accents. Surrounding greenery adds a touch of nature to the urban setting.
Apartment in Pittsburgh
4.89 out of 5 average rating, 400 reviews

Walk to Attractions. Downtown View. Stay in Style.

Walk to stadiums, downtown, strip-district, and cultural district! This recently-renovated historic hill-side duplex offers views of downtown and the Allegheny riverfront from almost every room. Stylish modern-industrial design with a wide open kitchen/living/dining room layout. Huge bathroom includes soaker tub with a view. Back deck sits above the roof and has panoramic downtown views that are second to none in the city. This unit is a 3rd floor walkup with steep steps.

Top Guest favourite
A cozy living area features a tan leather sofa adorned with decorative pillows, positioned in front of a modern electric fireplace. A rustic coffee table made from wood and a striped rug add warmth. In the background, a glimpse of the kitchen and dining space is visible.
Home in Pittsburgh
5 out of 5 average rating, 18 reviews

Prime Location | 2 Parking Spaces | Luxury Home

You will love this home from the moment you lay eyes on inviting front porch featuring modern siding and the custom designed and built sturdy white oak door. This light-filled, open concept 3 bedroom and 2.5 bathroom home is the ideal short term housing for busy professionals such as physicians, business executives, professors, and families who are looking for a quiet oasis to rest and recharge, but still be close to hospitals, downtown, and in the heart of trendy Lawrenceville.

Top Guest favourite
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 Pittsburgh
4.96 out of 5 average rating, 141 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!

Top Guest favourite
The living area features a large flat-screen TV mounted on a light wood media cabinet. A round black coffee table is centered on a textured gray area rug. Two windows provide natural light, and framed artwork is displayed on the wall.
Apartment in Pittsburgh
4.96 out of 5 average rating, 163 reviews

Off Street Parking, King Bed, on Butler Street!

Free off-street parking right on Butler Street? Check! Welcome to your home away from home, located on arguably the hippest street in Pittsburgh. 20+ bars & restaurants, 3 breweries, and more within three blocks - an active traveler's dream! If you would rather stay in, we have a great work from home space with two desks in separate rooms (perfect for traveling couples), a well stocked kitchen, two smart 4K TVs, comfy couch, and more!

Superhost
A modern living area features a vibrant orange sofa and two black accent chairs, arranged around a circular coffee table. A textured area rug lies beneath. A wall-mounted television is positioned above a sleek white fireplace, while a doorway leads to a dining area in the background.
Apartment in Pittsburgh
4.78 out of 5 average rating, 73 reviews

The Millvale Retreat

A modern 2-bedroom apartment in the heart of Millvale, located just across the Allegheny River from Lawrenceville district and only 10 minutes away from Pittsburgh downtown. You will find yourself in a safe and friendly neighborhood, walking distance from local restaurants, bars, breweries, and a convenience store. Situated equally close to all major attractions, universities, hospitals, and businesses of central Pittsburgh.

Popular amenities for Herrs Island holiday rentals