Holiday rentals in Pittsburgh

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Top-rated holiday rentals in Pittsburgh

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Top guest favourite
A dining area is depicted with a round wooden table set for four. Light gray chairs surround the table, complemented by decorative placemats. A woven light fixture hangs above, and a door with a window allows natural light to enter. A small closet and a wall-mounted plant holder are visible.
Home in Kingston
4.98 out of 5 average rating, 152 reviews

City Retreat With Board Games

Welcome to our newly renovated detached home! The fully stocked kitchen, smart TV, board games and patio offer convenience and entertainment. Unwind on the patio with high end patio furniture and a barbecue. Enjoy our central location in Kingston for a memorable stay. This property has a garden suite on the back of the property with a separate entrance and backyard space. We look forward to hosting you! Fully licensed for short term rentals with the City of Kingston - License #LCRL20250000092

Guest favourite
A canoe is positioned in calm water, reflecting the vibrant autumn foliage and cabin on the adjacent shore. The scene showcases a serene landscape with trees displaying red and green leaves, surrounded by still water that mirrors the surroundings.
Cabin in Battersea
4.86 out of 5 average rating, 202 reviews

The Hideaway: Private waterfront getaway

Looking for a therapeutic retreat? Clear your mind as you breathe in the clean air and watch the swans swim by. Cozy, newly renovated cabin with loft on Milburn Bay which leads to the Rideau. Canoe, life jackets, wood stove, electricity, AC,BBQ, WIFI and parking for one vehicle. Three occupants only, number to be confirmed when booking. Bring your own drinking water, bedding, pillows and slippers. New indoor composting toilet. Please read entire listing. No pets, please.

Top guest favourite
A comfortable living area features two brown armchairs and a spacious light-colored sectional. A mounted flat-screen television remains positioned above a wooden media console. A round mirror is displayed above a fireplace, contributing to the cozy ambiance of the space.
Home in Kingston
5 out of 5 average rating, 175 reviews

The Urban Cottage on Earl

The Urban Cottage on Earl is located in the heart of Kingston's historic Sydenham Ward and is within 2-3 blocks of KGH, Hotel Dieu, Queen's University, Lake Ontario and Kingston's vibrant downtown. Whether you are coming to Kingston for work or play, The Urban Cottage has all the conveniences of a downtown city home coupled with a relaxed cottage feel. After a long day, enjoy the fully enclosed, private backyard oasis complete with hot tub and water feature. LCRL20230000005

Top guest favourite
A wooden dock extends over calm waters, leading to a small aluminum rowboat moored nearby. Surrounding trees offer natural shade, and the sky is partly cloudy with light reflections on the water's surface. A serene landscape invites moments of relaxation and connection with nature.
Home in South Frontenac
4.98 out of 5 average rating, 129 reviews

The Lakeview cottage

Our cottage is the perfect place to relax with family or a few friends, and enjoy the peace and quiet surrounded by beautiful scenery. It is very private and you will have the entire property and cottage to yourself. it’s the perfect peaceful hideaway. The cottage is warm and cozy with gorgeous views of cranberry lake Our place is Great for nature walks, biking, swimming and enjoying the outdoors. Also for fishing/ice fishing and snowmobiling trails are close by.

Guest favourite
The entrance of the cottage is framed by lush green trees, featuring a wooden walkway leading to a welcoming porch. A rich orange door offers a pop of color, while various shrubs and flowers enhance the natural setting.
Home in Perth Road
4.95 out of 5 average rating, 120 reviews

Luxury Cottage in the Woods

Tranquil luxury cottage nestled in the woods. This cottage is located down a beautifully treed winding driveway and nestled in the trees. Take a walk down our laneways and trails and enjoy our gardens and pasture or enjoy your private space in the pergola for some quiet moments outdoors. This cottage is a hidden gem and is perfect for a quiet getaway. Come relax and explore this beautiful property. Note: There is absolutely NO SMOKING anywhere on this property.

Top guest favourite
A charming cottage exterior is framed by lush greenery. A metal roof and blue wooden siding complement the three front windows and central door, while orange daylilies add a pop of color to the surrounding garden. The front porch features steps leading to the entrance.
Cottage in Leeds and the Thousand Islands
4.97 out of 5 average rating, 397 reviews

Lyncreek Cottage

Lyncreek Cottage is open year round. it sits on private property on Lyndhurst river in Lyndhurst, Ontario. Observe various types of waterfowl or enjoy the sound of our meandering river as it flows into Lyndhurst Lake. This is all part of the natural surroundings in your own private cottage. A great place to stay if you are travelling through the area or while enjoying all the area has to offer including excellent fishing, paddling and hiking area trails.

Guest favourite
The spacious living area showcases two sofas and an ottoman, complemented by a wooden dining table surrounded by four chairs. A large window allows natural light, illuminating a 50-inch Smart TV on a media console against the wall.
Flat in Kingston
4.91 out of 5 average rating, 243 reviews

The Sweet Suite

- This bright, peaceful and quiet private apartment has an abundance of amenities at your home away from home. Enjoy this space and explore what Kingston has to offer from its convenient central location. - Separate exterior entrance. - Sound treated ceilings and walls. - Beautiful wooded area, park, and walking paths behind the property. - Two tobogganing hills -Complimentary snacks. -Linens washed after each stay with o3 commercial grade laundry system

Guest favourite
A cozy sleeping area is highlighted by a spacious bed covered with a light blue blanket. Natural light enters through large windows adorned with tied-back curtains, revealing a view of a green outdoor space. A piece of contemporary wall art adds a colorful touch.
Guest suite in Kingston
4.81 out of 5 average rating, 243 reviews

Private Suite near Skeleton Park

Sunny private suite 700 m from the downtown hub with separate entrance & 3-piece bath overlooking back courtyard. Entire space & amenities in ONE ROOM. FREE 2nd guest FREE high-speed wifi FREE coffee & teas FREE filtered water FREE (shared) parking No special cleaning by guests. Walk to hospitals & grocery or take-out. Sit in the private sunny courtyard & train chickadees to eat from your hand. No house access. City STR license # LCRL20210000518

Top guest favourite
Four white Adirondack chairs are arranged in a grassy area, each with a colorful pillow. A small fire pit surrounded by stacked firewood is nearby, complemented by vibrant flowers and greenery in the background. The cottage is visible, featuring a grey exterior with dark windows.
Cottage in Kingston
4.94 out of 5 average rating, 354 reviews

The Crows Nest Cozy River Cottage in Kingston

Welcome to The Crows Nest, our cozy waterfront cottage with your own private swimming dock. Here you’ll find the simplicity of river life. It’s a real birders paradise and a great place for spotting wildlife like deer.Enjoy the cozy living space, private deck to enjoy magnificent sunrises and sunsets, and the special calm that is the St. Lawrence River in the heart of The 1000 Islands. License number LCRL20210000964.

Top guest favourite
The exterior of a cabin is presented, showcasing wooden siding adorned with climbing greenery. Large windows allow natural light to enter, with flower boxes situated beneath them. The structure is framed by trees, creating a harmonious blend with the natural surroundings.
Cabin in Verona
4.97 out of 5 average rating, 106 reviews

Place: Bright and Cozy Woodland Retreat

Cozy forest retreat perfect for a winter escape. Watch the snow fall through soaring windows and warm up by the wood stove. Enjoy a custom kitchen, heated floors, rain shower, claw foot tub, and a hot tub on the deck under the stars. The bright open layout features a pull-out king daybed and forest-view bedroom. Steps from the lake, 25 mins to Frontenac Park, 40 mins to Kingston—your peaceful nature getaway awaits.

Top guest favourite
A modern kitchen area features a wooden island with a bowl of fruit at its center. White dining chairs surround a circular table. Exposed wooden beams enhance the ceiling, and stainless-steel appliances are neatly arranged. Light reflects off tiled backsplashes, creating a bright and inviting space.
Farm stay in Battersea
5 out of 5 average rating, 289 reviews

Soul Horse and Nature Retreat

The one-bedroom studio is a newly renovated abode in a century-old barn. It was created with the intention that guests will have the experience of peace and calm. All natural materials, right down to the organic latex bed and soft cotton sheets. Warm in the winter, cool in the summer, light-filled year-round.

Top guest favourite
A spacious studio apartment features a large bed with crisp linens, complemented by decorative pillows. A seating area with a dark sofa and armchair offers comfort. Double glass doors lead to the private patio, and framed artworks add a touch of color to the walls.
Flat in Kingston
4.89 out of 5 average rating, 253 reviews

The River Landing

The River Landing is a peaceful lower-level studio apartment; just steps away from the Cataraqui River and a short walk from Kingston’s downtown. A private entrance, self-check-in, and a secluded patio allow you to settle in right away. LCRL20230000132

Popular amenities for Pittsburgh holiday rentals

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