Waterfront holiday rentals in Pickering

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Top-rated waterfront rentals in Pickering

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

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Top guest favourite
A charming cabin is nestled among tall evergreen trees, surrounded by well-maintained landscaping. Stone steps lead to the entrance, illuminated softly by exterior lights. The lush green lawn flows gently, creating a serene outdoor setting.
Cabin in Whitchurch-Stouffville
4.99 out of 5 average rating, 129 reviews

Lakefront getaway for two on Musselman's Lake

An amazing getaway space for two and your dog on beautiful Musselman's Lake, close to Toronto but feels like you're in the Muskokas. This rustic designer one-bedroom cabin is the original attached cottage that our house grew from. Sit at the dock or on your patio to watch the spectacular sunsets. Have a coffee in the backyard and watch the sunrise over 160 acres of trails out your back door. This is your retreat with high-speed internet, full-size kitchen & dining area to enjoy cottage life.

Top guest favourite
A modern two-story cottage is surrounded by lush greenery and trees. The exterior features a combination of natural wood and dark green siding. A covered porch is visible with a personal entrance and outdoor seating. Bicycles are parked nearby, enhancing the outdoor activities available.
Guest suite in Toronto
4.95 out of 5 average rating, 222 reviews

Cozy small newly built Toronto Islands getaway

Escape to a modern cottage on Toronto Island Looking onto Lake Ontario is our newly constructed modern home. Enjoy our cozy private guest suite in our family home with a kitchenette, ensuite bathroom, and private entrance Just a quick ferry ride from the bustling downtown core come explore the Toronto Islands which is the biggest car-free community in North America; with beaches, trails & skyline views as well as an amusement park in the summer. We also have 2 bikes you can use to explore.

Guest favourite
A tree house is nestled among tall trees, featuring a wooden structure with a balcony and staircase. Soft sunlight filters through the branches, highlighting the natural wood finish and the serene forest surroundings.
Treehouse in Port Perry
4.97 out of 5 average rating, 559 reviews

Treehouse on private, isolated forest (300 acres)

You will feel like you're a thousand miles from Toronto. Your own private space with several ponds for swimming, gazebo, fire pits, running water, hot shower, mtn bike and hiking trails. With 300 acres at your door step, you can choose not to see another soul during your stay or venture to a nearby winery, restaurants, shopping, horse farms, golf courses or ski hills! We are just 1 hour from Toronto with easy access off the 407. We also have an amazing log cabin for rent on the same 300 acres.

Top guest favourite
The city skyline is illuminated at night, featuring the CN Tower prominently lit in red. A mix of modern skyscrapers reflects various colors, with a clear sky and moon visible in the background, highlighting the vibrant atmosphere of Toronto.
Apartment in Downtown Toronto
4.98 out of 5 average rating, 163 reviews

Amazing Views, King Bed, Easy Access to World Cup!

Easy access for those going to FIFA World Cup events! Enjoy views from the large balcony with great views of the CN Tower, Lake Ontario and Toronto skyline! King size bed. Ideal for couples, solo guests, friends or those in town for work. Steps from Union Station with instant access to all major transit. Short walk to CN Tower, The Harbourfront, sports/concert venues, the Entertainment District, restaurants and shopping. No additional guests permitted. Please read the rules section in full!

Superhost
A hot tub is positioned on a patio, providing views of the serene lake and distant horizon. Red outdoor chairs surround a firepit, while an umbrella offers shade nearby. The scene is framed by lush greenery and a stony beachfront, enhancing the tranquil setting.
Cottage in Bowmanville
4.88 out of 5 average rating, 190 reviews

“Lakeside Dreams”: All season HotTub w/lake views

Escape to our stunning lakefront family cottage! Enjoy breathtaking views, modern comforts, and the serenity of cottage life. With a private beach, firepit, BBQ, and covered patio, relaxation is guaranteed. Explore the nearby conservation area's trails or cast your line at the fishing creek, just a short walk away. A public beach is 5 min walk. Indulge in the perfect blend of nature and convenience. Book your stay now and create unforgettable memories in our charming cottage retreat!

Guest favourite
The modern three-story residence features a mix of stone and siding, characterized by large windows that allow natural light to fill the interior. A rooftop terrace is visible, providing a perfect spot for outdoor relaxation, alongside two garages located at the ground level.
Villa in Bowmanville
4.92 out of 5 average rating, 160 reviews

Grand Waterfront Retreat – Under 1hr from Toronto

Experience the ultimate in refinement and relaxation on the north shore of beautiful Lake Ontario. Luxurious waterfront 5000 sq ft modern house with an incredible 180 degree view of Lake Ontario. Just 5 minutes walks to Port Darlington Marina & beach. This brand-new house with modern high-end furnishings and decor in the prestigious Lakebreeze community is something you don't want to miss. Enjoy sunrise and sunsets directly from the house. All this is only 40 minutes away from Toronto!

Top guest favourite
A modern living area is depicted, featuring a dark sofa adorned with decorative pillows and a light wooden coffee table. A circular dining table with white chairs is in the foreground, while a wall-mounted TV is positioned opposite. Warm lighting enhances the spacious feel.
Flat in Richmond Hill
4.96 out of 5 average rating, 424 reviews

Modern Cozy Home near the Mill Pond Park.

Our newly renovated basement apartment will enchant you with its contemporary style, brightness and coziness (large lookout windows, super bright!). It is fully furnished with style and attention to details so you can feel at home away from home. It is just a few steps away from the beautiful Mill Pond Park - a great place to immerse in the beauty of nature. The park has many lovely trails that you can explore. The apartment has everything you need to make your stay perfect.

Superhost
A glamping dome is set amidst a lush green landscape, reflected in a serene pond featuring lily pads and blooming flowers. Towering trees provide a natural backdrop, while a wooden deck extends from the dome, enhancing the outdoor experience.
Dome in East Gwillimbury
4.9 out of 5 average rating, 251 reviews

Deerleap Glamping Dome

Located close to the city, our four-season glamping dome offers a peaceful and unique escape. In winter, the snow-covered landscape creates a magical scene, while inside, the wood pellet stove keeps the dome exceptionally warm and cozy. Nestled on 10 acres of picturesque land and a stunning pond view, Enjoy everything you need—from upscale sanitary facilities to fast Wi-Fi. Whether you’re celebrating a birthday, an anniversary, or simply seeking quiet time in nature.

Guest favourite
A wooden dock extends into a serene lake, reflecting a clear blue sky with scattered clouds. Flower pots are positioned on the dock, while torches line the edges, contributing to a peaceful outdoor atmosphere.
Cottage in Richmond Hill
4.94 out of 5 average rating, 173 reviews

White Oak on Wilcox-Richmond Hill Lakefront Oasis

Welcome to The White Oak on Wilcox - a lakefront oasis in the heart of Richmond Hill, perfect for an all-season getaway. Located just 30 mins from Toronto, enjoy direct access to Lake Wilcox with beautiful sunset views from the private dock. This vacation home welcomes you to a relaxing and serene lakefront experience. Surrounded by numerous activities to enjoy year-round, this is the perfect home-away-from-home! Share your memories with us @whiteoakcottageco

Superhost
A serene landscape of golden grasses and vibrant trees reflects in calm water. The scene captures a natural environment, inviting contemplation and enjoyment of the surrounding flora and fauna.
Guest suite in Pickering
4.78 out of 5 average rating, 230 reviews

Muskoka on the City

Located in Rouge National Urban Park, steps from a beautiful lake and beach(Note:beach was temporarily closed by government now).Enjoy hiking, kayaking, biking, and fishing nearby. Close to Toronto Zoo, Seaton Trail, highways, restaurants, shopping malls, and Rouge Hill GO Station. Bright ground-level suite with a private entrance, kitchen, dining area, TV, bathroom, and queen bedroom. Includes Wi-Fi and laundry. Perfect for a peaceful and convenient stay!

Top guest favourite
Two green Adirondack chairs, positioned facing the lake, are placed on a spacious deck with a red side table nearby. Lush greenery surrounds the water, reflecting the serene clouds above, while residential homes line the opposite shore.
Guest suite in Brampton
4.94 out of 5 average rating, 157 reviews

Lakeside Unit & Breathtaking View! 15 Mins to YYZ!

Scenic lakeside walkout basement apartment with breathtaking view! Bright, clean and spacious. Full kitchen, washer and dryer for your convenience. Free WiFi and one parking. Located at the most prestigious area in Brampton - Professor's Lake. Out side of my house is a trail around the whole lake for around 3 kilometers. Wonderful for runners or simply walk around the lake to enjoy the nature.

Top guest favourite
A bright sitting area showcases a large stained-glass window, casting colorful light. Furnishings include a white leather sofa and glass coffee table, with soft pillows adding comfort. A well-stocked bookshelf stands nearby, and a vintage cabinet complements the decor.
Home in The Beaches
4.95 out of 5 average rating, 130 reviews

Luxury Beaches Home Gourmet Kitchen Private Garden

- Charming detached Century home on corner lot - Family-friendly, safe, quiet, leafy street - Steps to The Boardwalk on Lake Ontario - Many nearby boutiques, cafes & fabulous restaurants - Private garden oasis with the amazing deck - Street parking available (with purchase of permit) - 7 kms to downtown Toronto

Popular amenities for waterfront rentals in Pickering

When is the best time to visit Pickering?

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Avg. price€63€58€63€53€56€60€73€78€75€61€60€59
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Quick stats about waterfront rentals in Pickering

  • Total holiday rentals

    Explore 60 holiday rentals in Pickering

  • Nightly prices starting at

    Pickering holiday rentals start at €17 per night before taxes and fees

  • Verified guest reviews

    Over 2,490 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    60 of Pickering holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Pickering rentals

  • 4.8 Average rating

    Pickering stays are highly rated by guests – averaging 4.8 out of 5!

Destinations to explore

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