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.

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Guest favorite

Yurt in Mono

4.98 out of 5 average rating, 227 reviews

Yurt Soaring Heart Wellness Spa

Sustainable Yurt Lodging close to the Bruce Trail. There is plenty of privacy and nature to experience our 10-acre property. We harvest and sell teas from our herb gardens. Check online at Escarpment Gardens. Enjoy a soak in the hot tub, float on our pond, practice yoga, book a massage, relax by the wood stove, or an outdoor campfire under the stars. Check massage services online : Soaring Heart Wellness Simple camp style cooking or eat at a great local restaurant within a 5 minute drive.

Jul 8 – 15

G$22,940 GYD per night

Guest favorite

Loft in Barrie

4.95 out of 5 average rating, 190 reviews

The Penthouse | Luxury at the Lake

Live the good life at 'The Penthouse' on Lake Simcoe. This is a luxurious and historical loft with stunning views of the bay. It's beautiful, bright, clean and spacious - perfect for romance and adventure with friends. Steps to the sandy beach, waterfront trails and the heart of downtown. Enjoy a meal downstairs at the legendary 'Farmhouse Restaurant'. Perfect all-in-one wedding venue, room to get ready and a party downstairs. If you're looking to unwind or a night on the town, it's all yours!

Jun 10 – 17

G$34,340 GYD per night

Guest favorite

Apartment in Horning's Mills

4.96 out of 5 average rating, 255 reviews

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 next to the Bruce Trail. Close to Shelburne, Mansfield, Creemore, and many excellent restaurants (like The Globe and Mrs Mitchels). Only 40 minutes to the Scandinave Spa, Collingwood, Blue Mountain, and Wasaga Beach. Golf Courses are close by. A perfect retreat just north of Toronto.

Dec 16 – 23

G$16,603 GYD per night

Guest favorite

Condo in Innisfil

4.97 out of 5 average rating, 111 reviews

•#TheFridayFlat Luxury Poolside Retreat for Summer

Enjoy access to all of Friday Harbour's world-class amenities, including a golf course and sandy beach. Take a dip in the outdoor pool and explore the kilometres of scenic walking trails that wind through the Nature Preserve Located just a short drive from Toronto, Friday Harbour offers the perfect escape from city life. Spend your days exploring the shops and restaurants of the promenade, or venture out onto the lake. Come experience the ultimate waterfront getaway at Friday Harbour!

Oct 13 – 20

G$22,264 GYD per night

Guest favorite

Cottage in New Dundee

4.87 out of 5 average rating, 143 reviews

Safe and Clean Cozy Waterfront Cottage

Cozy waterfront cottage. Nestled in the woods on a private lane. Enjoy this cottage vacation while being only minutes from the city of Kitchener. Take in the fresh air, cast a rod in the lake, float around in a canoe, enjoy a fire under the stars, or just hang out on the deck. In winter, explore the frozen lake with skates or snowshoes. Propane fireplace is available for emergency heat only in winter. In the event of a power outage this would be the only heat available. We allow one pet.

Mar 30 – Apr 6

G$20,883 GYD per night

Guest favorite

Cabin in Erin

4.97 out of 5 average rating, 103 reviews

Rustic Beach House 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.

Jul 11 – 18

G$34,113 GYD per night

Guest favorite

Apartment in Fergus

4.95 out of 5 average rating, 132 reviews

Riverside Retreat

One bedroom self-contained apartment right on the bank of the Grand River in historic Fergus, Ontario. Very quiet. Spacious screened porch next to Grand River! Fifteen minutes walk (or less than five minutes drive) to downtown Fergus. Beautiful downtown Elora, Elora Gorge Conservation Area and Belwood Lake Conservation Area are all within a ten minute drive. Note that access is down a flight of exterior stairs and unfortunately is not suited for individuals with mobility challenges.

Sep 18 – 25

G$17,687 GYD per night

Guest favorite

Home in Cambridge

4.92 out of 5 average rating, 305 reviews

"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!

Oct 16 – 23

G$39,612 GYD per night

Guest favorite

Apartment in Richmond Hill

4.95 out of 5 average rating, 297 reviews

Modern Cozy Home near the Mill Pond Park.

Our newly renovated basement apartment will enchant you with its contemporary style, brightness and coziness (large lookout windows, super bright!). It is fully furnished with style and attention to details so you can feel at home away from home. It is just a few steps away from the beautiful Mill Pond Park - a great place to immerse in the beauty of nature. The park has many lovely trails that you can explore. The apartment has everything you need to make your stay perfect.

Dec 12 – 19

G$21,680 GYD per night

Guest favorite

Home in Cambridge

4.96 out of 5 average rating, 426 reviews

Idyllic Lakefront Home in the City - Unit 1 of 2

LIKE NOTHING ELSE in Cambridge or K-W! • FREE 4 elongated tubes to use • FREE Chocolate/Snack bars/Chips/Coffee/Tea • Top 1% airbnb bookings • Luxurious Bath Robes • 12km of Trails in Shades Mill Conservation Area • Living, dining, family room, 2 bedrooms & 2 full bath • FAST WIFI, Free Netflix, AC • Cottage life 4km south of 401 Cambridge Mill 3km 1 acre property with 2 Airbnb units & owner's part time home Love Nature you'll ♥ it here

May 28 – Jun 4

G$31,750 GYD per night

Guest favorite

Farm stay in Lincoln

4.97 out of 5 average rating, 349 reviews

Water Edge, Modern Log Cabin in Beautiful Orchards

Nestled among Niagara’s fruit trees, our newly renovated log cabin sits on the shores of 16 Mile Creek. The log cabin is a modern, meticulously maintained studio space, secluded from busy roads (perfect to work in). Relax with a morning coffee on our porch or enjoy an evening campfire while overlooking 16 Mile Creek. Amenities include a comfortable sitting area, large picture windows, kitchenette (with hotplate), breakfast bar, elegant bathroom, BBQ and more.

Dec 4 – 11

G$28,701 GYD per night

Guest favorite

Dome in East Gwillimbury

4.92 out of 5 average rating, 129 reviews

Deerleap Glamping Dome

Looking for a peaceful escape from the city? Our glamping dome offers just that, situated on 10 acres of picturesque land with trail, streams, and a stunning pond view. Perfect for a romantic retreat or a weekend getaway with the family, our dome is equipped with everything you need, from upscale sanitary to fast Wifi. Relax and enjoy the starry sky from the comfort of your bed, gather around the bonfire for s'mores , or explore nearby Lake Simcoe.

Jan 7 – 12

G$38,546 GYD per night