Holiday houses in Glen Osborne

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Top-rated holiday rentals in Glen Osborne

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Apartment in Downtown Pittsburgh
4.89 out of 5 average rating, 226 reviews

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!

Superhost
The houseboat features a stylish exterior with a green and white design, showcasing multiple windows that allow natural light. Railings and a deck provide access to the water, while a spacious roof deck adds to the outdoor experience.
Boat in Sewickley
4.7 out of 5 average rating, 50 reviews

"Unique Houseboat Stay in Pittsburgh”

Remodeled 1980-style houseboat, hidden along the beautiful rivers of Pittsburgh. Features two twin beds, one queen bed, and a futon, making it perfect for groups or families looking to enjoy a unique stay. We have a hot tub located at the rear of the houseboat, where you can unwind and take in the scenic views. Please note that our houseboat is located at a private dock that we also use for our Bowfishing charters, which may create some activity until 1:30 AM. We appreciate your understanding.

Top Guest favourite
The exterior of a welcoming house displays a covered front porch with a wooden railing and a set of steps leading to the main entrance. Hanging planters adorn the porch, and a light brown door is centrally positioned under a gabled roof.
Loft in Sewickley
4.92 out of 5 average rating, 145 reviews

Sewickley Village

STUDIO APARTMENT on lower level of house (basement) with 1 large window. A cozy space with a convenient short walk to Sewickley Village: grocery store, restaurants, sports bar, pharmacy, library, YMCA. You have the entire space to yourself. This is a LARGE 1 ROOM studio apartment. Total privacy and separate entrance. Beds are: 1 Queen bed and 1 sofa that can be used as a full size bed. *You may hear foot traffic & other noises above (pets, etc). If this is an issue this space is not for you.

Guest favourite
Tiny home in Sewickley
5 out of 5 average rating, 12 reviews

The Silo @ Red Mud Hollow Farm

Escape to something truly one-of-a-kind in this beautifully crafted grain bin silo guest house tucked into a peaceful, wooded setting in Sewickley, PA. Whether you’re looking for a romantic getaway, a quiet retreat, or a cozy home base near Pittsburgh, this brand-new build blends rustic charm with modern comfort. This isn’t just a place to stay — it’s an experience. From the unique architecture to the peaceful setting, The Silo offers the perfect blend of privacy, style, and accessibility.

Top Guest favourite
Townhouse in Mt. Lebanon
4.99 out of 5 average rating, 175 reviews

Private Mt Lebanon Retreat Near Airport/Downtown

Welcome to your home away from home! This recently remodeled townhouse offers the perfect blend of comfort and style, situated just 20 minutes from the air port and city’s major stadiums. Ideal for all travelers, our home is nestled in a peaceful suburb with easy access to public transportation, nearby parks, and charming small businesses and shops. • Two bedrooms featuring king-sized beds. • An expansive kitchen, complete with peninsula and breakfast bar. We look forward to hosting you!

Top Guest favourite
The entrance of the cottage is highlighted by a welcoming set of white stairs leading up to a covered porch. Lush green grass surrounds the path, while colorful flowers are seen along the base of the home, adding a touch of vibrancy to the exterior.
Home in Sewickley
4.93 out of 5 average rating, 104 reviews

Bright and Beautiful one bedroom Cottage

Beautiful one bedroom cottage within walking distance to Sewickley Village and just 20 minutes from downtown Pittsburgh. This property is impeccably clean, well maintained, and loaded with amenities. You'll find everything you need for your stay and enjoy 2 smart TV's, gas fireplace and wood burning stove, marble bathroom with whirlpool tub, private fenced back yard, large patio, fire pit, washer and dryer, central air and heat, baby grand piano, complete kitchen, and many extras.

Top Guest favourite
The charming facade of the house is visible, featuring a welcoming front porch with a swing. A well-maintained garden with blooming flowers borders the entrance. The front door is flanked by decorative sidelights and a house number plaque, creating an inviting first impression.
Home in Sewickley
4.98 out of 5 average rating, 221 reviews

The Sewickley House: Historic Charm-Modern Comfort

The Sewickley House is a charming, completely remodeled house located in the heart of Sewickley's historic district - a short walk to the Village of Sewickley with unique shops and restaurants. Located on a quiet and quaint street, you can relax on the front porch swing or enjoy the private back patio during your visit. With modern amenities and a focus on comfort, this house is a destination or enjoy the city attractions with a 20 minute drive to downtown Pittsburgh.

Top Guest favourite
An outdoor area features an oversized hot tub, complemented by a gas grill and two lounge chairs. The cabin's rustic log exterior is visible in the background, with trees providing a natural setting. A mix of cloudy skies and sunlight adds to the ambiance.
Cabin in Toronto
4.98 out of 5 average rating, 496 reviews

“Lil’ Cabin on the Hill” w Hot Tub and Pool Table

“Little Cabin” is a uniquely secluded hideaway perched on a private hillside setting. Warm and inviting, with indoor and outdoor areas of entertainment, the vibe is cozy and fun. Beautiful rustic interiors are highlighted with colorful modern design and comfort at every turn. Whether a getaway or business trip, your stay at “Little Cabin on the Hill” will be a memorable and welcome retreat. • • Gravel driveway is Steep with parking both at top and bottom of drive.

Guest favourite
The exterior of a two-story brick residence is displayed, featuring a sturdy roof and a welcoming front entrance. Lush green lawns surround the home, with trees and other buildings visible in the background, suggesting a tranquil neighborhood setting.
Home in Ambridge
4.97 out of 5 average rating, 197 reviews

Historic District Comfort

Keep it simple, go back in time, at this centrally-located private residence. An Old Economy Gem overlooking the courtyard, on a one-way street in the heart of the Historic Old Economy in Ambridge, Pa. This is a comfortable restored historic home and has been redone back to its original finishes with upgrades on all new infrastructure and appliances. Conveniently located just off Route 65 North, 16 miles from downtown Pittsburgh, direct and easy commute.

Top Guest favourite
Home in Sewickley
5 out of 5 average rating, 12 reviews

Bright & Airy Retreat

Step into a beautifully renovated 3-bedroom, 2-bath home blending historic charm with modern comfort. Enjoy a fully equipped kitchen, cozy living room, high-speed Wi-Fi, and plush linens. Relax on the front porch swing or unwind in the private backyard. Located on a quiet street just 1 mile from Sewickley Village shops and dining, with easy access to Pittsburgh Airport and downtown. Perfect for families, business travelers, or extended stays.

Top Guest favourite
The exterior of a charming Cape Cod-style home features a welcoming front entrance with a decorative door and sidelights. Flanking the entrance, two neatly trimmed hedges are visible, and a flag decoration adds a festive touch. The home is set against a backdrop of overcast skies.
Home in Ambridge
4.94 out of 5 average rating, 201 reviews

Relax at Yellow Mellow

Relax at Yellow Mellow, a cozy home in a quiet neighborhood. Just a short drive to Pittsburgh (18 miles), Cranberry (12 miles), Sewickley (5 miles) and I-79. This older home has charm and character. Three bedrooms and two baths provide space to spread out. Dining room with seating allows for family meals with fully equipped kitchen. Rest and recharge from the porch swing, or relax in the fenced in yard with fire pit and covered patio.

Superhost
Apartment in Coraopolis
4.91 out of 5 average rating, 11 reviews

1BR Apartment near Pittsburgh Airport/Free Parking

This cozy 1 bedroom, 1 bathroom apartment is perfect for couples or business travelers looking for comfort and convenience near Pittsburgh. Located just minutes from Pittsburgh Airport and a short drive to downtown Pittsburgh, you’ll have easy access to everything while enjoying a comfortable stay. With a private entrance, dedicated parking, WiFi and a Smart TV, this space is designed to make your stay relaxing and stress-free.

Popular amenities for Glen Osborne holiday rentals