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
4.9 out of 5 average rating, 271 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!

Guest favourite
Apartment in Coraopolis
4.93 out of 5 average rating, 108 reviews

Cozy in Coraopolis Suite A

Recently updated 1 bedroom apt. with everything you will need for a comfortable stay. We have 2 Airbnb apartments available. We follow all Airbnb Community standards to provide a safe, quiet and comfortable experience for all and ask that you do the same. Minutes from the airport and a short drive to downtown Pittsburgh. Plenty of shopping and dining nearby. Perfect for out of town guests & business travelers. Live far from the airport and have an early flight? Come stay at Cozy in Coraopolis.

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
4.66 out of 5 average rating, 53 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
Tiny home in Sewickley
5 out of 5 average rating, 14 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, 181 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, 105 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
A private hot tub is illuminated in soft blue light, steam rising gently in the evening air. A nearby fence features string lights, contributing to the serene atmosphere. The scene suggests a relaxing outdoor space, ideal for unwinding after a day of activities.
Home in Columbiana
4.98 out of 5 average rating, 318 reviews

“The Thomas” House with Private Hot Tub

A picturesque countryside getaway with the convenience of shopping and restaurants nearby. If you love breweries, hot tubbing, golfing, cruising the neighborhood in a Model T golf cart, or just relaxing in a really cool house, this place is for you! Antiquing and open summer concerts minutes away. Comfort awaits in beautiful cozy interiors with vintage industrial vibe. With a touch of history and a lot of charm, your stay at “The Henry” will be a fun and welcome retreat.

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.

Superhost
Apartment in Coraopolis
4.76 out of 5 average rating, 25 reviews

2BR Apartment near Pittsburgh Airport/Free Parking

This cozy 2 bedroom, 2 bathroom apartment is perfect for families, small groups, 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.

Top Guest favourite
Home in Coraopolis
5 out of 5 average rating, 26 reviews

Cozy Cottage

Welcome to your cozy cottage getaway just 15 minutes from downtown Pittsburgh and Pittsburgh International Airport. This charming 2-bedroom, 1-bath home sleeps up to 4 guests and features a full kitchen with coffee maker, inviting fireplace, puzzles and board games, and fast Wi-Fi. Relax on the spacious deck or enjoy the peaceful wooded, fenced backyard. Private parking, washer/dryer, and a warm, homey atmosphere make it the perfect retreat.

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, 205 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.

Guest favourite
A cozy living area is highlighted by a soft sectional sofa facing a mounted flat-screen TV. A white brick fireplace serves as a focal point, while natural light filters through window coverings. A circular coffee table displays books and a decorative bowl.
Home in Sewickley
4.89 out of 5 average rating, 140 reviews

Boxwood House | Sewickley Retreat + Hot Tub

Welcome to Boxwood House, your stylish retreat in Sewickley Village, one of Pittsburgh’s most charming neighborhoods. This fully private 3BR home features an inviting hot tub, cozy fire pit, and designer details throughout. Walk to cafés, shops, and restaurants, or unwind in the backyard after a day in the city - located two blocks from Sewickley Village and just 20 minutes to downtown and 15 minutes to PIT Airport.

Popular amenities for Glen Osborne holiday rentals