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Waterfront holiday rentals in Caledon

Find and book unique waterfront rentals on Airbnb

Quick stats about waterfront rentals in Caledon

  • Total holiday rentals

    Explore 20 holiday rentals in Caledon

  • Nightly prices starting at

    Caledon holiday rentals start at $64 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,960 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Caledon holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Caledon rentals

  • 4.9 Average rating

    Caledon stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated waterfront rentals in Caledon

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

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Top guest favourite
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.
Flat in Horning's Mills

Beautiful Riverside Country Apartment

Bright, warm and newly renovated, this 900sqft apartment, a private floor of a charming country home with separate entrance and garden patio, awaits you in Melancthon. SmartHDTV, Wifi, tranquil surroundings, and the Bruce Trail. Close to Shelburne, Mansfield, Creemore, Pine River Institue and many excellent restaurants (The Globe and Mrs Mitchels). Only 40 minutes to the Scandinave Spa, Collingwood, Blue Mountain, Wasaga Beach. Golf Courses are close by. A perfect retreat just north of Toronto.

4.96 out of 5 average rating, 347 reviews
Guest favourite
A covered patio area features a hot tub alongside a glass-topped table with comfortable seating. The peaceful lakeside view showcases expansive green space and a row of chairs positioned along the shore, framed by trees lining the property.
Cottage in Georgina

Sunset Shores Lakehouse- Hot Tub, Wet Bar & Games

Welcome to Sunset Shores Lakehouse! Nestled in a tranquil bay on the shores of Lake Simcoe, this spacious family lake house is the perfect escape in all 4 seasons with many indoor and outdoor activities to enjoy! This peaceful waterfront retreat boasts 4 bedrooms + Wet Bar + Patio Oasis with lakeside Fire Pit + 6 person Hot Tub overlooking the lake and spectacular daily sunsets and sunrises you wont want to miss! Only 1 hour from Toronto and close to many Georgina attractions and adventures!

4.96 out of 5 average rating, 106 reviews
Guest favourite
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 OCTOBER 1 (1 night/2 days) discounted price for this one night 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 & direct Lakefront

4.96 out of 5 average rating, 332 reviews
Top guest favourite
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.

4.95 out of 5 average rating, 167 reviews
Top guest favourite
A private detached apartment is visible nestled among tall trees and lush greenery. The wooden exterior of the structure blends harmoniously with the natural surroundings. A pathway leads towards the entrance, framed by a vibrant landscape of ferns and colorful shrubs.
Guest suite in Caledon

Casa Caledon-Secluded Suite Surrounded by Nature

Take it easy at this unique and tranquil getaway, nestled on 3 acres of peaceful countryside Close to the Cheltenham Badlands, Forks of the Credit, Terra Cotta and Bruce Trail, plus golf, restaurants, bakeries and farm-fresh produce ❤️Every season is special 🌿 Enjoy lush forests, the pond and fire pit in spring & summer 🍁Spectacular fall colours and beautiful walks ❄️Peaceful winter wonderland with access to local winter sports A perfect place to slow down and reconnect with nature

4.98 out of 5 average rating, 164 reviews
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 Action

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.

4.85 out of 5 average rating, 159 reviews
Guest favourite
The exterior of the house features a combination of stone and wooden siding, with a pronounced roofline. A welcoming pathway leads to a spacious front deck, surrounded by manicured greenery and landscaping. Large windows and a colorful door enhance the inviting appearance.
Home in Alton

Cozy Fall Escape | HotTub + Fire Pit + River

Escape to the countryside this fall! Unwind in the hot tub under the stars, gather around the fire, and wake up beside the Credit River. Just under an hour from Toronto! 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

4.96 out of 5 average rating, 135 reviews
Top guest favourite
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.

4.96 out of 5 average rating, 167 reviews
Top guest favourite
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.
Shipping container in Puslinch

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!

4.99 out of 5 average rating, 128 reviews
Guest favourite
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.

4.96 out of 5 average rating, 418 reviews
Guest favourite
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!

4.93 out of 5 average rating, 476 reviews
Top guest favourite
Cabin in Guelph/Eramosa

Fern Hill Cabin

Escape to a hand-built Amish timber cabin on a peaceful 6-acre farm. Surrounded by willow trees, sheep, pigs, chickens, and a 150-year-old barn. It's your own country-spa retreat! Swim in the spring-fed pond, relax in the beautiful wood burning sauna, stargaze at night, and enjoy a compostable toilet with an unforgettable view! Restored century-old windows let in soft light and rustic charm. Ideal for anyone seeking quiet, nature, and a breath of fresh air.

4.99 out of 5 average rating, 114 reviews

Popular amenities for waterfront rentals in Caledon

KitchenWifiPoolFree parking on premisesAir conditioning

Waterfront apartment rentals

Top guest favourite
The exterior of a light-colored home is visible among tall trees, featuring large screened porch windows that invite natural light. A path lined with greenery leads to the entrance, enhancing the sense of seclusion near the Grand River.
Flat in Fergus

Riverside Retreat

4.94 out of 5 average rating, 264 reviews
Superhost
Flat in Elora-Salem

Elora Gingerbread Suite

4.81 out of 5 average rating, 627 reviews
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

Modern Cozy Home near the Mill Pond Park.

4.96 out of 5 average rating, 452 reviews
Guest favourite
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.
Flat in Downtown Toronto

Luxury Condo near CN Tower/Scotia Arena w/ parking

4.89 out of 5 average rating, 131 reviews
Top guest favourite
A bright living room is presented with a red and yellow color scheme. Two sofas, one in red and the other in a muted tone, are arranged around a circular coffee table. A wall-mounted TV is visible, alongside a cozy fireplace and large windows allowing natural light.
Flat in Elora-Salem

Casa Elora

4.98 out of 5 average rating, 661 reviews
Guest favourite
A modern sitting area features a sleek black couch accompanied by a light green throw blanket and decorative pillows. A small coffee table with magazines is placed on a patterned rug. Floor-to-ceiling glass doors provide access to a balcony with a view of the cityscape.
Flat in Downtown Toronto

Cozy 1BR Steps away from CNTower

4.9 out of 5 average rating, 104 reviews
Guest favourite
Flat in Downtown Toronto

Good Looking Condo Across from CN TOWER & MTCC

4.85 out of 5 average rating, 142 reviews
Top guest favourite
Flat in The Beaches

Stunning Beachfront Escape

4.97 out of 5 average rating, 101 reviews

Waterfront house rentals

Top guest favourite
A brightly lit living area features a red sofa adorned with decorative pillows. A wooden coffee table sits on a light rug, while large windows allow natural light to flood in, offering views of the surrounding greenery.
Home in Grand Valley

House on the bank of river

4.78 out of 5 average rating, 101 reviews
Guest favourite
A modern kitchen features sleek cabinetry and a large central island with seating for four. Pendant lights hang above the island, illuminating the space. Large sliding glass doors provide access to outdoor areas, enhancing natural light within the open layout.
Home in Hamilton

Luxurious 5BR Beach House with Firepit

4.9 out of 5 average rating, 189 reviews
Top guest favourite
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!

4.95 out of 5 average rating, 112 reviews
Guest favourite
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.
Home in Niagara-on-the-Lake

Waterfront Niagara-On-The-Lake Vineyard Farmhouse

4.94 out of 5 average rating, 120 reviews
Superhost
A spacious living area is presented with large windows offering sweeping views of the waterfront. A modern sectional sofa faces a coffee table, while dining chairs surround a sleek table in the background. Natural light fills the room, highlighting polished flooring and elegant decor.
Home in Hamilton

Palatial Waterfront Stay - HOT TUB & 2 King Bed

4.83 out of 5 average rating, 110 reviews
Guest favourite
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.

4.94 out of 5 average rating, 564 reviews
Top guest favourite
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

4.95 out of 5 average rating, 130 reviews
Guest favourite
A scenic sunset over the lake highlights the serene outdoor space, featuring a deck with a fire pit. A hot tub offers relaxation under the pergola. An aerial view of the property showcases the house surrounded by well-maintained grounds and easy access to the waterfront.
Home in Lincoln

Amazing Lake-Front Retreat w/ Hot Tub + WOW Views!

4.92 out of 5 average rating, 346 reviews

Waterfront apartment rentals

Guest favourite
A spacious living area is furnished with a comfortable sectional sofa and a coffee table, complemented by an area rug. Natural light floods in from a large window, illuminating the modern kitchen with wood cabinetry and bar seating in the background.
Apartment in Elora-Salem

Riverview!, A Gorgeous Condo on the Grand

4.93 out of 5 average rating, 192 reviews
Top guest favourite
Apartment in Downtown Toronto

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

4.96 out of 5 average rating, 194 reviews
Guest favourite
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

4.82 out of 5 average rating, 123 reviews
Guest favourite
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.
Apartment in Downtown Toronto

Luxury Entire Condo At Downtown+parking

4.93 out of 5 average rating, 159 reviews
Guest favourite
A modern living area features large windows offering panoramic city views. A sleek 70" smart TV is mounted on one wall, while a contemporary glass coffee table stands in front of a plush gray sofa adorned with soft throw pillows. Natural light fills the room.
Apartment in Downtown Toronto

3 Bedroom CN Tower Waterfront Oasis

4.94 out of 5 average rating, 144 reviews
Guest favourite
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.
Apartment in Downtown Toronto

Lakeside Condo /Pool/ Walking Trail/Parking/CNE

4.95 out of 5 average rating, 163 reviews
Guest favourite
An aerial view captures the iconic CN Tower against a clear blue sky. The skyline of downtown Toronto is featured prominently, showcasing a blend of modern skyscrapers and construction projects. The scene embodies a vibrant urban atmosphere with unobstructed city and lake views.
Apartment in Downtown Toronto

Brand New Condo Downtown Toronto beside CN Tower

4.94 out of 5 average rating, 137 reviews
Guest favourite
Apartment in Downtown Toronto

Steps to CN Tower/Waterfront | 2BR/2BA + Parking

4.88 out of 5 average rating, 160 reviews

When is the best time to visit Caledon?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$173 SGD$176 SGD$175 SGD$161 SGD$176 SGD$171 SGD$175 SGD$230 SGD$172 SGD$187 SGD$171 SGD$172 SGD
Avg. temp-7°C-6°C-1°C6°C12°C17°C20°C19°C15°C9°C3°C-3°C

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