Holiday rentals in Pittsburgh

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Top-rated holiday rentals in Pittsburgh

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Guest favourite
Guest suite in Kingston
4.91 out of 5 average rating, 150 reviews

Comfortable & quiet basement suite in Host's home

Your home away from home! Private apartment in lower level of house in Kingston's east end. Two bedrooms, fireplace, dartboard, Netflix, kitchenette and a spacious living room to relax in. All linens, toiletries and dishes are provided. Keyless entry through the shared front door. Driveway parking. We are 3km south of 401, 4km to RMC, 6km to downtown, and 8km to Queen's. Child's cot & playpen available (infants don't count towards # of guests). Questions? Send me an inquiry. Lic#LCRL20230000607

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.

Guest favourite
A cozy bedroom features a double bed with a decorative blanket, accompanied by bedside tables. Natural light enters through the window, illuminating the room. A door leads to the outside, enhancing the space's brightness.
Flat in Queens
4.82 out of 5 average rating, 178 reviews

Bachelor Apt close to Queen's/Downtown Kingston

This third-floor apartment is VERY close to Queen’s University as well as Lake Ontario and historic downtown Kingston. The private, third-floor entrance is at the back of the house and at the top of two flights of outdoor, narrow, metal stairs (the original fire escape). The homeowners live on the first two floors. Making this the ideal space for someone looking for a quiet space close to Queen's and downtown Kingston. No parking provided. It has air conditioning.

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, 122 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, 400 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, 248 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, 245 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

Guest favourite
An outdoor hot tub sits in the backyard, featuring clear blue water under a serene sky. Surrounding trees provide a natural backdrop, while the fenced area ensures privacy. The scene reflects a peaceful ambiance, ideal for relaxation any time of the year.
Flat in Kingston
4.93 out of 5 average rating, 206 reviews

City Central Retreat With HotTub & Mini Golf

Discover urban comfort in our newly renovated 3-bedroom main floor apartment. Centrally located in Kingston on a main street, minutes from downtown, enjoy easy access to city attractions. Unwind in the spacious hot tub or enjoy a fun afternoon on the putting green. Parking for 1 vehicle is available at the house. You'll have exclusive access to the main floor and backyard of this 2 unit house. Your perfect getaway awaits!

Top guest favourite
A spacious bed is centered within the room, dressed in neutral linens. Soft lighting is provided by bedside lamps. A television is mounted on the wall opposite the bed, complemented by a low dresser in an inviting green hue. Subtle artwork is displayed on the walls.
Flat in Kingston
4.96 out of 5 average rating, 112 reviews

The Harbour Landing

The Harbour Landing is a bright and welcoming lower-level studio apartment. A short walk from Kingston’s downtown and just up the road from a beautiful river walk, this apartment is the perfect landing place after a busy day of working or site seeing! The private entrance and self-check-in allow you to come and go as you please! LCRL20230000132

Top guest favourite
Cottage in Kingston
4.97 out of 5 average rating, 268 reviews

Waterfront cottage close to downtown Kingston.

We welcome our guests to our cozy and pet friendly waterfront cottage, Rube's Retreat. Enjoy the beauty of cottage living, very close to City Hall, downtown Kingston. Rube's Retreat is a great place to be, whether it's with your family, friends or a business trip, we have everything you need to make your getaway a most memorable experience.

Popular amenities for Pittsburgh holiday rentals

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