Waterfront holiday rentals in Caledon

4.96 out of 5 average rating, 321 reviews

The exterior of the guest house features a wrap-around composite deck with glass railing, overlooking the direct waterfront views of Lake Ontario. The structure is surrounded by lush greenery and is complemented by large windows allowing natural light into the living space.

Guesthouse in Lincoln

Cottage On Lake Ontario Niagara

OPEN TIMESLOTS JULY 9-10 (1 night/2 days) today JULY 16-18 (2 nights/3 days) JULY 25-3 Please mark this listing as a favourite to get notifications of last minute deals. Unwind at our cozy guest house. Beautiful 2-bedroom cottage. Enjoy the direct waterfront views from the living room, bedroom and wrap around composite deck. Outdoor fire pit and BBQ. Set in vineyards, peach, nectarine and plums. Close to wineries & shops. Free Tesla charging. Views from the cottage include orchards and the Lake.

4.94 out of 5 average rating, 225 reviews

The entrance of the container home is visible, featuring a wooden deck surrounded by trees. A wooden chair and small table offer a cozy seating area. The deck is enclosed by a glass railing, providing an unobstructed view of the natural surroundings.

Farm stay in Lincoln

Inn The Orchard, Valley View, Modern Container

Enjoy the sounds of nature when you stay in this unique place. Our newly renovated "Valley View, Container Home" in beautiful Niagara at Inn The Orchard, has been designed with all luxuries of home but created guaranteeing a relaxing atmosphere and simplicity that you'll never forget. We love creating spaces allowing you to escape the city and be surrounded by nature while remaining in the heart of Niagara's Wine Country! Enjoy this unique spot surrounded by fruit orchards on the valley edge.

4.95 out of 5 average rating, 155 reviews

An open concept living area showcases large panel doors that fully open to the outdoor deck. Inside, a comfortable seating arrangement is visible, along with a cozy area rug and a neutral color palette. Natural light floods the space, enhancing the connection to nature.

Cottage in Mono

Hockley Riverside Cottage • Loft and Bunkie

Needing an unforgettable escape? This cozy cottage is nestled in nature along the Nottawasaga river and has large panel doors that fully open for picture worthy views & peaceful sounds of the river. A new incredible outdoor fire-pit with hanging egg chairs. A cozy indoor wood burning fireplace along with a comfy pull out couch that has a projector above for the best movie nights. Heated floors if you aren't interested in maintaining a fire, fully equipped kitchen, Wi-fi, AC and washer/dryer.

4.86 out of 5 average rating, 142 reviews

An aerial view captures the waterfront trailer set against lush greenery, with a private deck featuring seating arrangements. Nearby, two kayaks await by the water, and a fire pit is surrounded by logs. The tranquil lake reflects the surrounding foliage.

Tiny home in Acton

Lakefront 1 bedroom tiny home

Reconnect with nature at this unforgettable escape. Enjoy a wonderful stay in our lovely waterfront trailer located on Breezes Trailer park. It is a private quiet trailer park with 15 acres of nature and private access to Fairy Lake (Acton). Trailer is suitable for couple or small family. It is suited to people looking to relax and enjoy the scenery, explore the lake on kayak, exercise and explore on water bikes, fishing in the lake, enjoy some outdoor movies or campfire or under the stars.

4.95 out of 5 average rating, 151 reviews

A spacious living room is depicted, featuring a light-colored sofa with decorative cushions and a woven throw. A coffee table with a marble-like surface sits in front, alongside a side table supporting a modern lamp. Soft lighting enhances the welcoming ambiance.

Guest suite in Brampton

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.

Shipping container in Puslinch

The exterior of a modern, dark-toned tiny home is framed by trees. A private dock with Adirondack chairs sits by the water, reflecting the structure's warm lights. The tranquil setting is enhanced by the surrounding natural landscape and evening ambiance.

4.99 out of 5 average rating, 115 reviews

Wildwood Tiny Home Escape with Wood Fired Sauna

Welcome to an absolutely unique converted shipping container – Wildwood Tiny Home! This converted shipping container has a big personality! If you and your guests are looking for luxury, nature, peace, serenity, and a chance to escape the city – this getaway is perfect for you! At Wildwood Tiny Home, you can fill your time with hanging out on your own private beach & waterfront dock, enjoying your firepit, beach volleyball, horseshoes, cornhole, badminton, board games, and many more!

4.96 out of 5 average rating, 169 reviews

The rustic beach house is surrounded by greenery, featuring wooden siding and a welcoming porch. A separate structure is visible nearby, both enhancing the tranquil setting. The clear blue sky adds to the serene atmosphere of the property.

Cabin in Erin

Rustic Cabin on Private Pond

Our Rustic Beach House is simply furnished and set on you very own private pond with a private beach. It has electricity, does not have plumbing. Fresh drinking water is supplied. Bathroom is a clean, private outhouse and you have access to our guest shower facility on premises from 6-9 am/pm daily. As your Bed and Breakfast host we will personally greet you and check you in and always remain on property while offering you privacy. We are designed for a quiet, peaceful rustic getaway.

4.93 out of 5 average rating, 468 reviews

A sunroom features a mixture of wooden furniture, including a sectional sofa and lounge chairs, arranged around a central table. String lights hanging overhead provide warm illumination, while large windows offer views of the surrounding nature.

Home in Cambridge

"Cottage Home On The River" 1 Bedroom

Welcome to Speed Island Trail! Nestled on 1 Acre property in a forested area that backs onto the Speed River. Enjoy Beautiful views all season long with large floor to ceiling windows and wildlife right outside your door. It is just like being out at the cottage. This beautiful one bedroom house is beautifully decorated, has a large kitchen and a breakfast bar. Enjoy the large sunroom and deck where you can sit back and relax. Added bonus the Chickadees eat right off your hand!

4.97 out of 5 average rating, 400 reviews

The modern tiny home features a black exterior and a large glass front, allowing natural light to illuminate the interior. A simple outdoor seating area with two chairs is visible, surrounded by lush greenery and trees, creating a connection with the serene natural surroundings.

Tiny home in Arthur

Luxury tiny home on peaceful country estate

Escape to Heirloom Tiny Home - where macro luxury meets a micro footprint. Nestled on 23 peaceful acres, surrounded by aspen and pine forests, just 10 minutes from the picturesque town of Elora. Wake up to serene pond views as horses and sheep graze in your view. Organic linens, artisanal soaps, and a spa-like bathroom soothe the senses. Cozy up by the indoor fire and gaze at the stars. Enjoy fine dining at the Elora Mill and Spa, enjoy popular shops or hike the Elora Gorge nearby.

4.97 out of 5 average rating, 126 reviews

The exterior of a two-story house showcases a blend of stone and dark wood siding, with a spacious deck accessible from the upper floor. Lush green grass and neatly arranged flower beds surround the home, while a gray sky sets a calm backdrop.

Home in Alton

Cozy Country Spring Getaway | HotTub + Fire Pit

Escape to the countryside this spring 🌸 Unwind in the hot tub or pool, enjoy cozy fires under the stars, and soak in the peaceful charm of Alton. Perfect for a relaxing getaway, girls weekend, or quiet work-from-home retreat. • Sleeps up to 8 guests comfortably • 3 cozy bedrooms (2 with private decks!) • 1.5 bathrooms • Fully equipped kitchen + BBQ patio for year-round grilling • Stylish living room with fireplace & smart TV • Fast Wi-Fi, workspace-friendly

4.93 out of 5 average rating, 142 reviews

A white dome structure is nestled among lush trees, positioned beside a calm pond. The surrounding landscape features vibrant greenery and a clear blue sky, creating a peaceful outdoor setting. The area suggests space for leisurely activities by the water.

Dome in East Gwillimbury

Chirping-Paradise Glamping Dome

Looking for a quick escape close to the city? Our glamping dome offers a serene retreat on 10 acres of trails, streams, and a peaceful pond. Perfect for birthdays, anniversaries, and family gatherings, it blends nature with a touch of luxury. In winter, enjoy the snowy outdoors and stay warm inside with the wood pellet stove. Thoughtfully designed for comfort and romance, with upscale amenities and fast Wi-Fi, it’s the ideal spot to create unforgettable memories.

4.99 out of 5 average rating, 200 reviews

A unique double A-frame house is framed by lush greenery, with a spacious driveway leading to the entrance. The structure features a combination of wood and stone elements, while flower beds with emerging blooms add color to the natural surroundings.

Cottage in St. Jacobs

St. Jacobs Triangle House - Countryside Escape

Welcome to Triangle House, a unique double A-frame situated on a private 1.7 acre lot, fronting on the Conestogo river Only 6 minutes drive from St.Jacobs center, 1.5 hours drive from Toronto, 15 minutes drive from the University of Waterloo and 25 minutes to Elora. Bring the whole family. This 3 bed, 3 bath home comfortably sleeps 6. Soak in the countryside from the sprawling deck and grounds, while enjoying all the comforts of a modern home.

Popular amenities for Caledon waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment accommodation

A modern bedroom features a spacious bed with a patterned comforter and two neatly arranged towels. Floor-to-ceiling windows provide a bright atmosphere, offering views of the cityscape. A decorative plant is placed near the window, and a wall-mounted TV adds to the room's convenience.

4.97 out of 5 average rating, 122 reviews

All New CN Tower View Condo on the 35+ Floor

Apartment in Horning's Mills

A private wooden deck is shown with an umbrella-covered table and four chairs, surrounded by lush greenery. Windows on the building's façade allow natural light, while potted plants add a touch of color, enhancing the outdoor space for relaxation.

4.96 out of 5 average rating, 336 reviews

Beautiful Riverside Country Apartment

4.97 out of 5 average rating, 212 reviews

A spacious living area features a modern leather sofa complemented by a stylish coffee table. A workspace with a desk and chair is present, with natural light streaming in from the window. Decorative elements include wall art and a serene color scheme.

Apartment in Hamilton

Harbour House

4.89 out of 5 average rating, 117 reviews

1BR+sofa with waterfront views

A spacious living area is highlighted by a large black and white artwork on the wall. A dark sectional sofa is positioned across from a sleek glass coffee table, with two white chairs nearby. Warm lighting from table lamps adds to the modern aesthetic.

4.96 out of 5 average rating, 101 reviews

Lakeview Condo in the heart of Downtown Toronto

4.82 out of 5 average rating, 609 reviews

Apartment in Elora-Salem

Elora Gingerbread Suite

A vast view from the private balcony overlooks the iconic CN Tower, framed by a vibrant blue sky and fluffy white clouds. The urban skyline is visible, showcasing a blend of modern buildings and architectural features.

4.92 out of 5 average rating, 119 reviews

45+ Floor Downtown Condo w Stunning CN Tower View

A spacious balcony offers panoramic views of Toronto's skyline, including the iconic CN Tower nearby. Outdoor seating arrangements are visible, providing a place to relax while enjoying the cityscape. Clear skies and scattered clouds enhance the bright atmosphere of this high-floor location.

4.89 out of 5 average rating, 118 reviews

Luxury Condo near CN Tower/Scotia Arena w/ parking

Waterfront house rentals

4.9 out of 5 average rating, 263 reviews

A patio area with a table and four chairs is visible, positioned directly beside the water. The tranquil lake extends into the horizon, with soft waves created by the gentle breeze. A muted sky adds to the serene atmosphere.

Home in Hamilton

Stunning Home on Lake Ontario

4.94 out of 5 average rating, 536 reviews

Two light blue chairs are positioned near a tranquil lake, with a bottle of wine and a glass resting on a wooden table. A sign displaying 'LIVE THE LIFE YOU'VE IMAGINED' is set upright on the ground, surrounded by greenery and soft grass.

Home in Cambridge

Shades Mill Lake - Unit 1 of 2. 3rd Bed available.

4.99 out of 5 average rating, 128 reviews

Home in Lincoln

Lakehouse on the Vineyard in Lincoln-Beamsville!

4.96 out of 5 average rating, 323 reviews

Home in Port Dalhousie

Lux Lake Ont Beachfront - Fire Pit & Sunset Views

4.94 out of 5 average rating, 108 reviews

A hot tub is positioned on a deck overlooking a calm, expansive lake. The water reflects soft gray skies, creating a serene atmosphere. Rocky shoreline is visible in the foreground, enhancing the tranquil lakeside setting.

Home in Hamilton

Wake Up To Lake Views!

4.96 out of 5 average rating, 112 reviews

A comfortable seating area is showcased with a dark leather couch and a wooden coffee table. Natural light filters through two large windows, revealing views of the serene pond and lush greenery outside. The room is complemented by framed photographs on the wall.

Home in Kitchener

Cottage In The City

Home in Niagara-on-the-Lake

A serene view of lush greenery features a winding stone path leading towards the sparkling waters of the Niagara River. Tall trees cast gentle shadows over the expansive grassy area, creating a peaceful outdoor atmosphere.

4.95 out of 5 average rating, 131 reviews

🥂Breathtaking Views of the Niagara River

Home in Niagara-on-the-Lake

The farmhouse exterior is showcased, featuring a white clapboard facade complemented by a stone chimney. Vibrant rose bushes add color near the entryway, while lush greenery enhances the natural surroundings. Large windows provide a welcoming appearance amidst a well-maintained lawn.

4.95 out of 5 average rating, 111 reviews

Waterfront Niagara-On-The-Lake Vineyard Farmhouse

Waterfront condo accommodation

A small balcony features a bistro table and two wooden chairs, overlooking a serene view of Lake Ontario. A potted plant sits in the center of the table, with the shimmering water and distant shore visible in the background.

4.97 out of 5 average rating, 336 reviews

Lively 1+1 Lakeview Condo near CN Tower + Free Prk

A bright bedroom features a spacious bed dressed in crisp white linens, topped with a soft, textured throw. Natural light fills the space through a large window, accented by elegant curtains. A small nightstand with a lamp and a decorative plant adds to the calming atmosphere.

4.85 out of 5 average rating, 111 reviews

**30%OFF** Lake view property ❤️ of downtown

A modern living area features a dark couch adorned with decorative pillows, positioned beside a glass coffee table. A stylish bookshelf occupies the wall, displaying plants and decorative objects. A large flat-screen TV is mounted on the wall, enhancing the entertainment options.

4.95 out of 5 average rating, 153 reviews

Lakeside condo/Pool/Rooftop Hottub/ParkingFIFAzone

A contemporary waterfront condominium complex is visible, showcasing multiple glass-fronted balconies and lush greenery surrounding the entrance. The building features an urban design with large windows, allowing for abundant natural light, under a vibrant blue sky with scattered clouds.

4.89 out of 5 average rating, 467 reviews

Lakeside Condo Studio In Downtown Toronto

4.81 out of 5 average rating, 115 reviews

A spacious living area is featured, with large windows offering natural light and views of the city. A comfortable gray sofa is situated alongside a vibrant red armchair. A wooden coffee table rests on a patterned rug, complemented by a flat-screen TV and decorative artwork.

Condo in Etobicoke

Humber Bay Family Friendly condo w Terrace&Parking

A modern living space features a light-colored sofa adorned with decorative pillows. A coffee table with various items sits in front of a wall-mounted television. Large windows allow natural light to fill the area, showcasing views of the city beyond.

4.92 out of 5 average rating, 145 reviews

Luxury Entire Condo At Downtown+parking

A comfortable living area is highlighted by a plush sofa adorned with decorative pillows. A sleek television is positioned on a wooden media console, while a vibrant area rug adds warmth. Large windows offer natural light and views of the cityscape.

4.99 out of 5 average rating, 169 reviews

Artsy and Comfy Home with a View

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.