
Waterfront holiday rentals in Pickering
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Pickering
Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

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.

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.

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.

1BR+sofa with waterfront views
Start your day with the breathtaking view of Lake Ontario and the stunning Toronto skyline! Whether you're visiting Toronto for business or leisure, the vibrant downtown core is undoubtedly the heart of this beautiful city. How better to enjoy it all than in a 1BR + sofa bed suite in downtown Toronto. You'll be near the CN Tower, Ripley's Aquarium, Rogers Centre, and the city's greatest restaurants and entertainment. Don't miss this wonderful opportunity in the city's most dynamic location!

Lake Guest Suit> 15 mins YYZ>private whole place
You will enjoy this newly renovated private space! Located on the edge of beautiful Professor's Lake, a walk-out basement apartment with a separate entrance, spacious living room, bright bedroom, jet shower bathroom, comfortable king-size bed and new kitchen. Everything separated from upstairs. Private access to the lakeside path from the backyard. Enjoy your morning breeze from the lake when you walk around the lake. A lot of natural beauties, birds, fishes, turtles and great lake views.

“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!

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!

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.

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.

Romantic Nature Retreat - Hydrotherapy Suite
A Romantic Retreat, located on 91 acres, beside a small, spring-fed lake, this is a private hydrotherapy suite with its own sitting area and firepit, providing a relaxing getaway close to the city. Gentle walking trails and abundant wildlife around the lake Swimming, dock, canoe & paddleboat Ideal for two people, 2SLGBTQ+ all welcome 6 min drive to Newcastle for dinner, shopping... Please read reviews & full ad before booking. Pets are welcome.

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!

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.
Popular amenities for waterfront rentals in Pickering
Waterfront apartment rentals

Spacious 2BR in Prime Downtown by CN Tower

New 40th+ floor Direct View of CN Tower and Lake

FIFA Location: Amazing Lake View Studio CN Tower

Lake Breeze Apartment, EV Charging & Free Parking

45+ Floor Downtown Condo w Stunning CN Tower View

Luxury Condo near CN Tower/Scotia Arena w/ parking

Oasis by the Lake

Luxury Escape Apt to Relax with Kitchen & Parking
Waterfront house rentals

Leslieville Luxury Home 4BR Entertainer's Dream

pet friendly waterfront Cottage-Bowmanville

Private river access with pool, canoes, kayak

Chic 1-Bdrm Suite Steps to The Beaches & Boardwalk

Bright Spacious Sun Filled Oasis w/ Parking

Private Suite - Ajax by the Lake

Luxury & Modern Home in Thornhill, Parking, Yard

Blissful Lakeview Retreat | Waterfront Cheateau
Waterfront apartment rentals

2BR Condo | Balcony + Parking by CN Tower & Scotia

FIFA Fan Zone Pool-Hottub-Free Parking Walk to BMO

Humber Bay Family Friendly condo w Terrace&Parking

Luxury Entire Condo At Downtown+parking

3 Bedroom CN Tower Waterfront Oasis

Sleek 40+ Floor Oasis with CN Tower and Lake Views

Beautiful Lake View Studio Condo + 1 free Parking

Artsy and Comfy Home with a View
When is the best time to visit Pickering?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $93 SGD | $86 SGD | $93 SGD | $78 SGD | $82 SGD | $88 SGD | $107 SGD | $115 SGD | $110 SGD | $89 SGD | $88 SGD | $87 SGD |
| Avg. temp | -3°C | -3°C | 2°C | 8°C | 14°C | 20°C | 23°C | 22°C | 18°C | 11°C | 5°C | 0°C |
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 $26 SGD 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
- Montreal Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Mississauga Holiday rentals
- Hudson Valley Holiday rentals
- Pocono Mountains Holiday rentals
- Island of Montreal Holiday rentals
- Capital District, New York Holiday rentals
- Northeast Ohio Holiday rentals
- Grand River Holiday rentals
- St. Catharines Holiday rentals
- Niagara Falls Holiday rentals
- Rentals with a patio Pickering
- Apartment rentals Pickering
- Smoking-friendly rentals Pickering
- Rentals with outdoor seating Pickering
- Rentals with a hot tub Pickering
- Rentals with a fireplace Pickering
- Townhouse rentals Pickering
- Rentals with pools Pickering
- Pet-friendly rentals Pickering
- Rentals with a washing machine and dryer Pickering
- Fitness-friendly rentals Pickering
- Cottage rentals Pickering
- Rentals with an EV charger Pickering
- Rentals with lake access Pickering
- Family-friendly rentals Pickering
- Rentals with breakfast Pickering
- Guest house rentals Pickering
- House rentals Pickering
- Rentals with a firepit Pickering
- Private suite rentals Pickering
- Rentals with beach access Pickering
- Flat rentals Pickering
- Beachfront rentals Pickering
- Waterfront rentals Durham
- Waterfront rentals Ontario
- Waterfront rentals Canada
- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Enercare Centre
- Metro Toronto Convention Centre
- BMO Field
- The Danforth Music Hall
- Harbourfront Centre
- Nike Square One Shopping Centre
- Distillery District
- Toronto Eaton Centre
- Exhibition Place
- Downsview Park
- Toronto Zoo
- Trinity Bellwoods Park
- Financial District
- Casa Loma
- Massey Hall
- Scarborough Town Center
- York University
- Dufferin Grove Park
- Lakeridge Ski Resort





