Waterfront holiday rentals in Greater Toronto and Hamilton Area

Oak Orchard Bliss: Angler’s Haven & Family Oasis

Welcome to Crooked Creek Property! There is so much to love about this cozy cottage right on Oak Orchard River. Let yourself in with the high-tech Nest keypad and get to enjoying the huge wrap-around deck that overlooks the Oak Orchard River. The property provides privacy and offers direct access to the River via a private walking path down the river bank. Enjoy your time on the creek fishing, kayaking, canoeing, swimming, or just enjoying the beauty of nature. We have Kayaks available to rent!

Woodcliff Cottage

Woodcliff Cottage on the shore of Lake Ontario, NY, has been fully renovated. A new kitchen features granite countertops, island/bar and spectacular views. The kitchen opens into a spacious living room with gas fireplace and more windows looking out over the new deck and Lake Ontario. Enjoy a sunset campfire at the fire pit with stairs leading down to Lake Ontario. 2 Bedrooms, 2 baths with walk-in shower and shower with full bathtub. We also rent Shell Cottage next door. Falls a 20 minute drive.

Lakehouse on the Vineyard in Lincoln-Beamsville!

Escape to peace and quiet and relaxation! Charming rustic farmhouse cottage nestled in a stunning 100 acre working vineyard with magnificent views of Lake Ontario and the Toronto Skyline. Little slice of heaven! Perfect for relaxation. Close to all winery routes, restaurants and Niagara Falls attractions. One hour from Toronto and minutes away from numerous outdoor activities for all ages including the Charles Daley Beach, Bruce Trail, Balls Falls Conservation Area and Niagara Wine Country!

Retreat 82

Located just a little over an hour from Toronto, this cozy and unique lakefront cottage is the perfect place for a relaxing couples getaway. Offering private access to Lake Scugog with an oversized dock for you to take advantage of water activities, enjoy your morning coffee and watch some of the best sunsets on the lake. The cottage sits only 15 min. from the quaint town of Port Perry where you can go to enjoy its brewery, incredible cuisine, farmers markets, and picturesque Main Street.

Cottage On Lake Ontario Niagara

OPEN TIMESLOTS MARCH 24 (1 night/2 days) MARCH 27-30 (3 nights/4 days) APRIL 1 (1 night/2 days) 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: Lake

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!

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.

Inn The Orchard, Modern Log Cabin, on water edge

Nestled among Niagara's fruit trees, our newly renovated log cabin sits on 16 Mile Creek. This modern studio is secluded, perfect for work or relaxation. Enjoy a morning coffee on the porch or an evening campfire with creek views. The cabin includes a comfortable sitting area, large windows, kitchenette (with hotplate), breakfast bar, elegant bathroom, BBQ, and more. Sauna and Cold Plunge available for all guests, included in the price for ultimate relaxation during your stay.

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.

Waterfront Hillside Villa

Welcome to your stunning Hillside Villa situated on 150' of waterfront. Enjoy the peaceful surroundings and quiet Bay views from your 3 private outdoor decks & hot tub. Entertaining is easy in this gourmet kitchen, which is open to 1 of 2 fireplaces, family room & dining room with floor to ceiling views of the Bay. Breathe taking views of the Bay from your private dock. Hidden gems: gym, 2nd kitchen, foosball table, EV charging and private trail.

The Nook, Peaceful Retreat: Lake+Hot Tub+ Sauna!

Heritage barn turned zen-den! Our open-concept, loft style, timber-frame cabin has exposed beams, barn board walls, and plenty of windows to enjoy the lake view. Decorated with a beachy boho meets mid-century vibe, it's cozy and airy at the same time! The private deck offers the perfect place to listen to the birds and read a good book. The Nook is on our 1 acre, lakefront property, alongside our home. We hope you love it here as much as we do!