
Holiday houses in Glen Osborne
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Top-rated holiday rentals in Glen Osborne
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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.

The “Dreamcatcher” Treehouse with Private Hot Tub
The "Dreamcatcher" Treehouse is a unique secluded hideaway perched high above the scenic ravine and rolling creek. In an enchanted wooded setting, a winding gravel pathway leads to the whimsical rope suspension bridge entering the treehouse. Stunning views await from floor to ceiling windows, and the spacious cantilevered deck with oversized hot tub and glass fire pit. With upscale modern design featuring beautiful cozy interiors and comfort at every turn, your stay will be a welcome retreat.

Urban Oasis Home - Hot Tub, Pet-friendly, Koi Pond
This charming historical home is close to everything! You can be downtown within 5 minutes. You'll be minutes from the stadiums, museums, and the casino! Pamper yourself. Relax in the hot tub while listening to the sounds of the waterfall over the pond. Watch the colorful Koi splash and play. The meticulously landscaped grounds have countless surprises and beauty in every season. You will enjoy every comfort in this luxurious three-bedroom and 2.5 baths. There's even a shower for your furbaby!

Moon Professional Living Suite B
Recently updated 1 bedroom 2nd floor efficiency apt. w/ everything you will need for a comfortable stay. We do have 2 Airbnb Apartments available. We follow all Airbnb standards to provide a safe, quiet, sparkling clean, comfortable experience for all & ask you do the same. Minutes from the airport & short drive to downtown Pittsburgh. Shopping & dining nearby. Perfect for out of town guests & business travelers. Live far from the airport & have an early flight? Come stay at Cozy in Coraopolis.

Gorgeous Modernized Cabin + Hot Tub + Pool Table
Welcome to this incredible, fully renovated true log home with a massive entertainment room consisting of a pool table, ping pong table and more 🔥 3 full sized bedrooms along with an additional room with a pull out couch. There are 3 private bedrooms or use it as 4 with a wall separation. Fully equipped kitchen with quartz countertops and stainless appliances. Large front porch with plenty of furnishings and a rear deck with a view of a farm. Huge 2 car garage for parking and a driveway! 🚘

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.

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.

Historic Charmer | Spacious | Off Street Parking
Charming 2-Bedroom Apartment in Historic Victorian Home Bright and inviting second-floor unit in an 1887 Queen Anne Victorian. Features a private entrance, staircase, and deck with stunning views of the Ohio River and Emsworth Lock and Dam. Just 6 miles from Heinz Field, PNC Park, and 15 miles from Pittsburgh International Airport. One block from public transportation. Set on a spacious lot with gardens, fruit trees, and a magnificent oak tree.

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.

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.

A Retreat Above It All
This is a second floor apartment overlooking a large park-like lot in the close Pittsburgh suburbs. It has an eclectic mix of furnishings that makes it both cool and comfortable. Fully furnished and well-stocked with everything you’ll need for your stay - whether a weekend or a week. This unit can be combined with the downstairs unit for an additional bedroom and bath.

Green Street Guest House
Enjoy a stylish and comfortable experience at this renovated home located in the Sewickley central business district surrounded by shops, restaurants and entertainment. Full brick walls and radiant heat keep it warm in winter and cool in summer. Atmospheric accent lighting, original painted artwork and eclectic whimsical decor sets a festive tone for your stay.
Popular amenities for Glen Osborne holiday rentals
Other great holiday rentals in Glen Osborne

Royal Garden Cottage: 2 Bedrooms, Quiet Retreat

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Pittsburgh Home, with Fabulous City & River Views!

Airport Bungalow

130 Yr Old Whimsical Gem On 1.3 River Front Acres

Elegant Family Haven

Modern Bellevue Retreat – 10 Min to Downtown

Family Home in Glenshaw
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Washington Holiday rentals
- Mississauga Holiday rentals
- Philadelphia Holiday rentals
- Pocono Mountains Holiday rentals
- Grand River Holiday rentals
- Northeast Ohio Holiday rentals
- St. Catharines Holiday rentals
- Pittsburgh Holiday rentals
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- PNC Park
- Carnegie Mellon University
- David Lawrence Convention Center
- Acrisure Stadium
- Pittsburgh Zoo & PPG Aquarium
- University Of Pittsburgh
- Point State Park
- Raccoon Creek State Park
- National Aviary
- Kennywood
- Phipps Conservatory and Botanical Gardens
- Schenley Park
- Sri Venkateswara Temple
- Carnegie Museum of Art
- Petersen Events Center
- Stage AE
- Children's Museum of Pittsburgh
- Senator John Heinz History Center
- Randyland
- Cathedral of Learning
- Carnegie Science Center
- McConnells Mill State Park
- PPG Paints Arena
- Hollywood Casino at the Meadows





