Waterfront holiday rentals in Caledon

4.97 out of 5 average rating, 298 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.

Guest house in Lincoln

Cottage On Lake Ontario Niagara

OPEN TIMESLOTS MAY 16-31 (May long weekend still open checkin Saturday) JUNE 1-30 J 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: lakefront and orchards.

4.94 out of 5 average rating, 216 reviews

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

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.

4.95 out of 5 average rating, 149 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.

Superhost

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

4.85 out of 5 average rating, 124 reviews

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, 140 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, 106 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, 161 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, 452 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, 381 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.

4.98 out of 5 average rating, 121 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

4.95 out of 5 average rating, 170 reviews

Dome in Zephyr

Glass Dome - Sleep Under The Stars- Free Sundays

Discover this new, stunning 22ft Glass Geodesic Dome nestled in the heart of Uxbridge. Imagine waking up surrounded by 360-degree panoramic views of the natural landscape Please note... its FULL WEEKEND STAYS ONLY - BOOK FRIDAY AND SATURDAY-SUNDAY IS FREE. This allows guests to fully enjoy their Sunday without feeling rushed to check out at 11am. Enjoy all day Sunday with option of staying the evening. 8X12 BUNKIE NOW AVAIL. SLEEPS 4 ( 2 bunk beds)

4.99 out of 5 average rating, 192 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 waterfront rentals in Caledon

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

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.

4.96 out of 5 average rating, 110 reviews

All New CN Tower View Condo on the 35+ Floor

4.97 out of 5 average rating, 202 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.

Flat in Hamilton

Harbour House

4.88 out of 5 average rating, 105 reviews

1BR+sofa with waterfront views

A bright living area features a large smart TV on a white media console. A cozy sofa is complemented by decorative pillows. In the background, a spacious bedroom is visible through an open door, showcasing a comfortable queen bed with soft bedding. Floor-to-ceiling windows provide natural light.

4.91 out of 5 average rating, 129 reviews

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

A modern studio space features a queen-sized bed with soft linens, accompanied by a stylish lamp and wall art. A round dining table with two chairs is situated nearby, and large windows provide natural light, framed by elegant drapery.

4.85 out of 5 average rating, 158 reviews

FIFA Location: Amazing Lake View Studio CN Tower

Superhost

A spacious kitchen features a large island with bar seating and stainless steel appliances. Adjacent, a dining area showcases a wooden table surrounded by upholstered chairs, complemented by a stone accent wall. Soft overhead lighting enhances the inviting atmosphere.

Flat in Elora-Salem

4.82 out of 5 average rating, 605 reviews

Elora Gingerbread Suite

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, 114 reviews

Luxury Condo near CN Tower/Scotia Arena w/ parking

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.

4.96 out of 5 average rating, 111 reviews

45+ Floor Downtown Condo w Stunning CN Tower View

Waterfront house rentals

4.83 out of 5 average rating, 111 reviews

A white cottage is set against a clear blue sky, featuring a charming front porch with potted plants. A well-maintained lawn extends to the side, with a tree providing shade. The proximity to the river is visible, enhancing the inviting exterior.

Home in Lewiston

Right on the River! walking to town/artpark/docks

4.86 out of 5 average rating, 179 reviews

A sandy beach leads to a calm, blue body of water. A person in a red kayak glides along the surface, while another individual reclines on a pier, enjoying the serene view. The horizon features the meeting of the sea and sky under bright sunlight.

Home in The Beaches

Toronto Beach Paradise

4.99 out of 5 average rating, 119 reviews

A spacious outdoor seating area is depicted, featuring a large table shaded by a vibrant blue umbrella. Surrounding the table are six chairs with colorful cushions. Lush green grass extends into the background, where several lounge chairs and ornamental trees are visible, creating a serene environment.

Home in Lincoln

Lakehouse on the Vineyard in Lincoln-Beamsville!

4.87 out of 5 average rating, 253 reviews

Home in Youngstown

Lake Ontario Home+Hot Tub, sleeps 10 | Tucked Away

4.94 out of 5 average rating, 103 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!

Superhost

Home in Pickering

4.79 out of 5 average rating, 121 reviews

Beach House: First Floor

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.

4.96 out of 5 average rating, 126 reviews

🥂Breathtaking Views of the Niagara River

4.95 out of 5 average rating, 129 reviews

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

Luxury Beaches Home Gourmet Kitchen Private Garden

Waterfront apartment rentals

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, 326 reviews

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

4.96 out of 5 average rating, 173 reviews

Luxury Lakeview 3BR+2BA Condo • Subway & BMO Field

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, 148 reviews

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

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.

Apartment 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.

4.95 out of 5 average rating, 136 reviews

Luxury Entire Condo At Downtown+parking

A desk with an ergonomic chair is positioned near floor-to-ceiling windows, offering a stunning view of Lake Ontario at sunset. The scene features a vibrant sky with hues of orange and purple, along with glimpses of the surrounding greenery and cityscape.

4.98 out of 5 average rating, 105 reviews

Beautiful Lake View Studio Condo + 1 free Parking

The spacious living area features a comfortable sectional sofa, a glass coffee table, and a large smart TV positioned for easy viewing. Decorative art and plants enhance the ambiance, while a dining table for two is visible in the background, creating a functional and inviting space.

4.91 out of 5 average rating, 198 reviews

Sleek 40+ Floor Oasis with CN Tower and Lake Views

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.