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

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.

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.

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.

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.

Lakefront Cozy Cottage w Hot Tub!
On Lake Simcoe this cozy retreat is just an hour north of Toronto Enjoy the stunning sunrises / views and access to a variety of water activities, while the surrounding area provides ample opportunities for hiking, skiing, other outdoor pursuits with many amenities closely. Down the street from Friday Harbour, LCBO, Starbucks 5 star rating a must & ALL guests to be added to booking. Honey, our golden doodle will greet and visit with you. The cabin is to be left SAME as you found it.

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!

"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.

Cottage On Lake Ontario Niagara
OPEN TIMESLOTS MAY 5 (tonight) MAY 16-31 JUNE 1-30 JULY 1-31 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 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

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)

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

Charming Private 3 Bedroom Townhome Glen Williams

Elora Gingerbread Suite

45+ Floor Downtown Condo w Stunning CN Tower View

Luxury Clifton Hill -Skywheel Views-Mins to Falls!

Lovely 1-bedroom Basement Apartment on Niagara
Waterfront house rentals

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!

Beach House: First Floor

🥂Breathtaking Views of the Niagara River

Luxurious 5BR Beach House with Firepit

California Chic +Breathe +Unwind +Restore
Waterfront condo rentals

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

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

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

Pet friendly 2 BR with a private terrace at FH

Hidden gem in Humber bay shores Toronto w/ parking

Luxury Entire Condo At Downtown+parking

Riverview...A Gorgeous Condo on the Grand

Modern Lakeview Condo | Walk to CN Tower & Arena
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
Destinations to explore
- Greater Toronto and Hamilton Area Vacation rentals
- Greater Toronto Area Vacation rentals
- Mississauga Vacation rentals
- Pocono Mountains Vacation rentals
- Grand River Vacation rentals
- Northeast Ohio Vacation rentals
- St. Catharines Vacation rentals
- Pittsburgh Vacation rentals
- Niagara Falls Vacation rentals
- Erie Canal Vacation rentals
- Detroit Vacation rentals
- Cleveland Vacation rentals
- Condo rentals Caledon
- Fitness-friendly rentals Caledon
- Rentals with pools Caledon
- Rentals with a patio Caledon
- Rentals with a fire pit Caledon
- Private suite rentals Caledon
- Townhouse rentals Caledon
- Smoking-friendly rentals Caledon
- Rentals with a hot tub Caledon
- House rentals Caledon
- Rentals with outdoor seating Caledon
- Rentals with lake access Caledon
- Guesthouse rentals Caledon
- Apartment rentals Caledon
- Rentals with a washer and dryer Caledon
- Bed and breakfasts Caledon
- Family-friendly rentals Caledon
- Rentals with breakfast Caledon
- Pet-friendly rentals Caledon
- Rentals with an EV charger Caledon
- Rentals with a fireplace Caledon
- Waterfront rentals Peel
- Waterfront rentals Ontario
- Waterfront rentals Canada
- 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
- Distillery District
- Nike Square One Shopping Centre
- Toronto Eaton Centre
- Exhibition Place
- Toronto Zoo
- Trinity Bellwoods Park
- Downsview Park
- Snow Valley Ski Resort
- Financial District
- Wilfrid Laurier University
- Massey Hall
- Casa Loma
- Dufferin Grove Park





