
Waterfront vacation rentals in Caledon
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Top-rated waterfront rentals in Caledon
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Fire & Ice Spa w/ Private Sauna!
Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh and unwind in your very own private spa experience which includes large infrared sauna, 3 indoor fireplaces and outdoor fire table. Kiss those winter blues away while you warm up in the most cozy suite, perfect for a romantic getaway. Every stay includes a bottle of bubbly to toast with the one who is most important to you! Make Fire & Ice your next vacation destination and reconnect in a most romantic, relaxing suite!

Cottage On Lake Ontario Niagara
OPEN TIMESLOTS MAY 31-JUNE 4 (4 nights/5 days) book 1 or 4 JUNE 8-18 JUNE 21-JULY 6 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.

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.

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.

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.

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.

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!

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.

"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!

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.

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

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
Waterfront apartment rentals

All New CN Tower View Condo on the 35+ Floor

Harbour House

1BR+sofa with waterfront views

Elora Gingerbread Suite

45+ Floor Downtown Condo w Stunning CN Tower View

Lovely 1-bedroom Basement Apartment on Niagara

Luxury Clifton Hill -Skywheel Views-Mins to Falls!

Riverside Retreat
Waterfront house rentals

Luxury Pond House, 10 minutes to Niagara Falls

Lakehouse on the Vineyard in Lincoln-Beamsville!

Lux Lake Ont Beachfront - Fire Pit & Sunset Views

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

Wake Up To Lake Views!

🥂Breathtaking Views of the Niagara River

Luxurious 5BR Beach House with Firepit

Waterfront Niagara-On-The-Lake Vineyard Farmhouse
Waterfront condo rentals

Stunning 1BR w Pool ~ Free Parking & Self Check-In

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

Humber Bay Family Friendly condo w Terrace&Parking

Designer Condo with beautiful harbour view.

Luxury Entire Condo At Downtown+parking

Riverview...A Gorgeous Condo on the Grand

Modern Lakeview Condo | 2026 Match Stay

Resort Condo in Friday Harbour
When is the best time to visit Caledon?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ499 | ﺩ.ﺇ507 | ﺩ.ﺇ503 | ﺩ.ﺇ492 | ﺩ.ﺇ499 | ﺩ.ﺇ606 | ﺩ.ﺇ503 | ﺩ.ﺇ661 | ﺩ.ﺇ496 | ﺩ.ﺇ540 | ﺩ.ﺇ492 | ﺩ.ﺇ496 |
| Avg. temp | -7°C | -6°C | -1°C | 6°C | 12°C | 17°C | 20°C | 19°C | 15°C | 9°C | 3°C | -3°C |
Quick stats about waterfront rentals in Caledon

Total vacation rentals
Explore 20 vacation rentals in Caledon

Nightly prices starting at
Caledon vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

Verified guest reviews
Over 1,700 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Caledon vacation rentals include wi-fi 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!

Nearby attractions
Caledon's top spots, include SilverCity Brampton Cinemas, Landmark Cinemas 7 Bolton, and Uptown Theatre
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- Waterfront rentals Peel
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Enercare Centre
- Blue Mountain Village
- 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
- Snow Valley Ski Resort
- Financial District
- Casa Loma
- Wilfrid Laurier University
- Massey Hall
- Museum of Illusions





