Holiday houses in Glenshaw

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Top-rated holiday rentals in Glenshaw

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Top Guest favourite
An outdoor space is illuminated by soft string lights, featuring a hot tub surrounded by wooden decking. A gazebo with seating is nearby, and a fire pit is visible in the background, complemented by lush greenery and trees that create a private setting.
Home in Pittsburgh
4.95 out of 5 average rating, 120 reviews

Serene Secluded Hilltop Hideaway. Hot Tub Fire Pit

A peaceful escape close to the city. Nestled in a private wooded setting, this 4BR home is just 15 minutes from downtown Pittsburgh. Relax on a wrap-around balcony, unwind in the hot tub, or gather for conversation around the fire pit under the trees. With space for families, pets, and friends, plus trails just steps away, it’s a perfect blend of natural privacy and city convenience. The inside offers a refined treehouse vibe - with warm, modern interiors surrounded by serene woodland views.

Top Guest favourite
A spacious living area is furnished with a large sectional couch and a coffee table. Natural light floods in through three windows, and a ceiling fan is mounted above. Decorative wall art and woven wall hangings add texture to the neutral-toned walls.
Apartment in Bellevue
4.97 out of 5 average rating, 144 reviews

Desert Chic close to the city!

This 2nd floor two bedroom apartment is newly renovated, stylish and spacious. Tons of natural light shines through in every room to brighten your experience in this trendy neighborhood only minutes from downtown Pittsburgh. Conveniently located only 1 block from shops, a brewery, a bakery and multiple restaurants, as well as less than 10 minutes to Downtown Pittsburgh’s North Shore. This desert themed apartment will provide you with a comfortable convenient stay. Off-street parking is provided.

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 North Side
4.94 out of 5 average rating, 243 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.

Top Guest favourite
The exterior of a sunporch suite is displayed, featuring large wall-to-wall windows framed by white columns. A pathway leads to the entrance, surrounded by lush greenery, including a bush. The home showcases a charming blend of white and red brick, adding character to the facade.
Guest suite in Highland Park
4.98 out of 5 average rating, 302 reviews

Historic Sunporch Suite

Welcome! We are delighted to share with you our favorite room in an 1895 Georgian Colonial home. This comfortable sunporch suite is ideal for two guests or a family with a young child. Located in a safe, quiet, and wonderful section of Pittsburgh, we are close to the zoo and Children's Hospital, and a short drive from downtown. This suite has its own separate entrance, bathroom, and kitchenette. The wall-to-wall windows look over the front yard, courtyard, and our neighbor's Victorian home.

Top Guest favourite
Apartment in Lower Lawrenceville
4.95 out of 5 average rating, 128 reviews

Upscale DoubleKing Suite~Butler St~2 ParkingSpaces

2 OFF STREET PARKING SPACES 2 KING bedroom (+Full Size Sleeper Sofa) 1 bath apartment w/ a private patio steps from Butler St in Lawrenceville neighborhood! Sleeper Sofa and extra linens for bigger groups. Enjoy this stylish space in the coolest neighborhood in town, steps to dozens of restaurants, shops, coffee shops. Walk to UPMC Children's hospital and the Strip District, short drive to Downtown, North Shore, Shadyside, Oakland, Pitt, CMU, & several hospitals! Book your stay today!

Top Guest favourite
A cozy sleeping area is featured, showcasing a bed adorned with a decorative comforter in soft tones of beige and coral. A bedside lamp and a wooden nightstand provide functional décor, while an additional chair completes the space.
Guest suite in Gibsonia
4.94 out of 5 average rating, 193 reviews

Cozy Comfortable Retreat #1

Beautiful basement guest suite with a gas fireplace, full bath, kitchen with cooktop stove, mini refrigerator and microwave/convection oven. Enjoy off street parking in a quiet friendly neighborhood with outdoor patio. Close to shopping, restaurants, North Park and Hartwood Acres. Downtown Pittsburgh is less than 13 miles away which allows for easy access to all the sporting events Steeler games, Pirate games and Penguin games. Located less than 2 miles from the PA turnpike exit.

Guest favourite
The exterior of a three-story house is shown, featuring dark siding and a peaked roof. A welcoming front entrance is accessed via a steps leading to the door. Lush green shrubs frame the house, contrasting with the bright grassy area in front.
Apartment in Pittsburgh
4.91 out of 5 average rating, 509 reviews

Comfort Central

Comfort Central is in a very safe neighborhood with on street parking. It's 7 miles from downtown Pittsburgh, universities, stadiums, museums and 2 miles from RIDC Park in O'Hara Township. It' conveniently located within an 8 minute drive from the Pennsylvania Turnpike . There is a hospital and park nearby. The Waterworks Mall which includes grocery stores, retail shopping, restaurants, wine and spirits store, fast food , and movie theater is a short 5 minute drive.

Top Guest favourite
An inviting living space features a brown leather sofa and a window adorned with dark curtains. Natural wood paneling enhances the cozy atmosphere, while a small Christmas tree adds a festive touch. The open layout connects to a dining area with wooden chairs and table.
Cabin in South Park Township
4.99 out of 5 average rating, 102 reviews

The Lily Pad Cabin

Cozy cabin offers open floor plan with covered porch overlooking small pond on our property. Uniquely decorated. Views of woods & fields, but close to numerous restaurants, parks & walking trails, & TRAX Farms. The Trolley to Pittsburgh is two minutes away. Should you need single night accommodation, please message me for consideration. Also consider “Mojo’s Loft”, our pet-friendly rental or Jackson Hill Cabin, our full log home with three bedrooms & a pool table.

Guest favourite
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.
Townhouse in Central Lawrenceville
4.92 out of 5 average rating, 392 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!

Guest favourite
A cozy living room features a large red sectional sofa adorned with cushions. A round, dark wood coffee table sits on a light area rug, surrounded by two decorative bowls. A TV stand with a television and small plant adds functional decor, while an air conditioning unit is mounted on the wall.
Apartment in Millvale
4.95 out of 5 average rating, 197 reviews

*Comfy & Clean* 1BR Millvale apt

You will be close to everything when you stay at this centrally-located apartment in the heart of Millvale! Safe & friendly neighborhood with plenty of restaurants, diners, breweries, and bars in walking distance. You will be only a few feet from a convenience store. The famous Mr. Small’s theater is less than a half mile away! The beautiful River trail that leads to the north shore, Heinz field, PNC park, etc is only 1 mile!

Guest favourite
A cozy living area is presented with a brown leather couch adorned with decorative pillows. A wooden table sits in front, complemented by a green plant. Natural light streams in from sliding glass doors that open to a deck, while an abstract art piece decorates the wall.
Townhouse in Pittsburgh
4.91 out of 5 average rating, 191 reviews

Comfortable Family Retreat | Crib | Quiet & Safe

Nestled in the Shaler/ O’Hara neighborhood our home is the perfect for families looking to explore the vibrant city of Pittsburgh. With ample space for everyone to spread out and relax, our home offers a comfortable and inviting atmosphere. We offer premium amenities, including whole bean coffee, tea selection, soft towels, toiletries, and in-unit laundry (w/d) with laundry supplies provided.

Top Guest favourite
A house sign reading 'The Bungalow' is mounted on grey siding, surrounded by modern geometric decor. A vintage-style light fixture emits warm light, casting a welcoming glow, while greenery is visible in the background, enhancing the inviting atmosphere of the entryway.
Home in New Kensington
4.99 out of 5 average rating, 266 reviews

Cozy Cottage Bungalow

(Formerly the “MidCentury Burrell Bungalow) Located only 30 minutes from the beautiful city of Pittsburgh, this newly renovated home is nestled in a quiet, dog & family friendly rural neighborhood. While the home is playground-adjacent & located just up the hill from the rails-to-trails along the Allegheny River, the backyard is fenced in & perfectly suited for families & furry friends alike.

Popular amenities for Glenshaw holiday rentals