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Waterfront holiday rentals in Whitby

Find and book unique waterfront rentals on Airbnb

Quick stats about waterfront rentals in Whitby

  • Total holiday rentals

    Explore 30 holiday rentals in Whitby

  • Nightly prices starting at

    Whitby holiday rentals start at $39 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,380 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Whitby holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Whitby rentals

  • 4.8 Average rating

    Whitby stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated waterfront rentals in Whitby

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

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Top guest favourite
A charming cabin is nestled among tall evergreen trees, surrounded by well-maintained landscaping. Stone steps lead to the entrance, illuminated softly by exterior lights. The lush green lawn flows gently, creating a serene outdoor setting.
Cabin in Whitchurch-Stouffville
4.99 out of 5 average rating, 132 reviews

Lakefront getaway for two on Musselman's Lake

An amazing getaway space for two and your dog on beautiful Musselman's Lake, close to Toronto but feels like you're in the Muskokas. This rustic designer one-bedroom cabin is the original attached cottage that our house grew from. Sit at the dock or on your patio to watch the spectacular sunsets. Have a coffee in the backyard and watch the sunrise over 160 acres of trails out your back door. This is your retreat with high-speed internet, full-size kitchen & dining area to enjoy cottage life.

Guest favourite
A tree house is nestled among tall trees, featuring a wooden structure with a balcony and staircase. Soft sunlight filters through the branches, highlighting the natural wood finish and the serene forest surroundings.
Treehouse in Port Perry
4.97 out of 5 average rating, 559 reviews

Treehouse on private, isolated forest (300 acres)

You will feel like you're a thousand miles from Toronto. Your own private space with several ponds for swimming, gazebo, fire pits, running water, hot shower, mtn bike and hiking trails. With 300 acres at your door step, you can choose not to see another soul during your stay or venture to a nearby winery, restaurants, shopping, horse farms, golf courses or ski hills! We are just 1 hour from Toronto with easy access off the 407. We also have an amazing log cabin for rent on the same 300 acres.

Top guest favourite
A fire pit with flames is situated near the water's edge, surrounded by smooth stones. An Adirondack chair is positioned to face the lake, offering a view of the serene water and a colorful sunset in the background.
Guest suite in Port Perry
4.89 out of 5 average rating, 268 reviews

Sunset Haven

Cozy suite, this location provides the very best of the outdoors for cottaging enthusiasts 45 minutes from the GTA. Found on the outskirts of Port Perry near the Blue Heron Casino and on the shores of Lake Scugog, you will find great fishing, swimming, and boating at your doorstep. Also great lounging on the deck/dock! The casino is 5 min drive and the town of Port Perry with its good restaurants and shopping is 10 min car ride or take your boat! Unfortunately, no pets are allowed by guests.

Guest favourite
A lakefront cottage is set on a grassy area beside the water, featuring a wooden dock extending toward the lake. The exterior shows a welcoming porch and surrounding trees provide shade. Stone borders accentuate the shoreline, creating a natural beach-like atmosphere.
Cabin in Nestleton Station
4.92 out of 5 average rating, 204 reviews

Cozy, Quirky and Modern Lakefront Cottage

Welcome to the Scugog Sugar Shack! Just 70 mins away from Toronto, escape to enjoy picturesque sunsets at this cozy lakefront cottage nestled under the largest collection of mature sugar maples on Scugog Point. This 2 bedroom open concept 1940s cottage has been updated with all the creature comforts while staying true to its quirky roots. With private access to Lake Scugog, known for fishing, kayaking, paddle boarding and swimming, bask in the sun all day & sit by a fire under the stars.

Guest favourite
A rustic cabin is illuminated from within, set against a starry night sky. The structure features a covered front porch and a white door, flanked by two windows. Surrounding trees are silhouetted, adding a serene backdrop to the scene.
Guest house in Newcastle
4.89 out of 5 average rating, 340 reviews

Waterside Nature Cabin - Private & Comfortable

Small spring fed lake, 91 acres, privacy, solar powered, propane heat, gas stove & wi-fi. Pets welcome! To keep your costs low; No Cleaning Fee! However, you must clean up ALL mess and take your garbage/recycling home with you. No indoor washroom or running water. Clean private outhouse. Basic utensils, cutlery/bowls/plates, pots, and pans provided. This is and independent stay. Bring your own bedding, blanket, pillow, drinking water. Please leave the cabin better than you found it!

Superhost
A hot tub is positioned on a patio, providing views of the serene lake and distant horizon. Red outdoor chairs surround a firepit, while an umbrella offers shade nearby. The scene is framed by lush greenery and a stony beachfront, enhancing the tranquil setting.
Cottage in Bowmanville
4.88 out of 5 average rating, 193 reviews

“Lakeside Dreams”: All season HotTub w/lake views

Escape to our stunning lakefront family cottage! Enjoy breathtaking views, modern comforts, and the serenity of cottage life. With a private beach, firepit, BBQ, and covered patio, relaxation is guaranteed. Explore the nearby conservation area's trails or cast your line at the fishing creek, just a short walk away. A public beach is 5 min walk. Indulge in the perfect blend of nature and convenience. Book your stay now and create unforgettable memories in our charming cottage retreat!

Guest favourite
The modern three-story residence features a mix of stone and siding, characterized by large windows that allow natural light to fill the interior. A rooftop terrace is visible, providing a perfect spot for outdoor relaxation, alongside two garages located at the ground level.
Villa in Bowmanville
4.9 out of 5 average rating, 164 reviews

Grand Waterfront Retreat – Under 1hr from Toronto

Experience the ultimate in refinement and relaxation on the north shore of beautiful Lake Ontario. Luxurious waterfront 5000 sq ft modern house with an incredible 180 degree view of Lake Ontario. Just 5 minutes walks to Port Darlington Marina & beach. This brand-new house with modern high-end furnishings and decor in the prestigious Lakebreeze community is something you don't want to miss. Enjoy sunrise and sunsets directly from the house. All this is only 40 minutes away from Toronto!

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
4.96 out of 5 average rating, 433 reviews

Modern Cozy Home near the Mill Pond Park.

Our bright and cozy basement apartment features large lookout windows and everything you need for a comfortable stay. Just steps from beautiful Mill Pond Park, enjoy scenic trails and a peaceful residential setting. Located in Richmond Hill, about an hour from downtown Toronto. A vehicle is recommended. Free parking included. Perfect for guests seeking a quiet retreat with easy access to the city and ideal for nature lovers. Shops and restaurants are just a short drive away.

Top guest favourite
The image captures a serene lake at sunset, reflecting vibrant hues of orange and purple in the sky and water. A wooden dock extends into the calm water, providing a tranquil setting for evening activities.
Guest house in Port Perry
5 out of 5 average rating, 150 reviews

Lakeside Guest Suite, on Lake Scugog, Port Perry

WATERFRONT PROPERTY….Enjoy stunning sunsets from the basement walkout guest suite. Take in views from the living room, bedroom (queen bed), or large 34 foot long private patio! The backyard leads directly to the lake including a fire pit for your use. Please note that the natural slope of the yard (40 stairs) may not be suitable for those with mobility issues. While the suite doesn't feature a kitchen, Port Perry is only an 8 min drive and offers many culinary options.

Superhost
A glamping dome is set amidst a lush green landscape, reflected in a serene pond featuring lily pads and blooming flowers. Towering trees provide a natural backdrop, while a wooden deck extends from the dome, enhancing the outdoor experience.
Dome in East Gwillimbury
4.9 out of 5 average rating, 255 reviews

Deerleap Glamping Dome

Located close to the city, our four-season glamping dome offers a peaceful and unique escape. In winter, the snow-covered landscape creates a magical scene, while inside, the wood pellet stove keeps the dome exceptionally warm and cozy. Nestled on 10 acres of picturesque land and a stunning pond view, Enjoy everything you need—from upscale sanitary facilities to fast Wi-Fi. Whether you’re celebrating a birthday, an anniversary, or simply seeking quiet time in nature.

Superhost
Dome in Zephyr
4.93 out of 5 average rating, 183 reviews

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) $100 flat fee

Superhost
A tranquil view of a lake reflects the colorful hues of the sunset, with a modern building nestled among trees on the opposite shore. The surrounding landscape features gentle slopes leading to the water, creating a peaceful natural setting.
Guest suite in Newcastle
4.89 out of 5 average rating, 257 reviews

Romantic Nature Retreat - Hydrotherapy Suite

A Romantic Retreat, located on 91 acres, beside a small, spring-fed lake, this is a private hydrotherapy suite with its own sitting area and firepit, providing a relaxing getaway close to the city. Gentle walking trails and abundant wildlife around the lake Swimming, dock, canoe & paddleboat Ideal for two people, 2SLGBTQ+ all welcome 6 min drive to Newcastle for dinner, shopping... Please read reviews & full ad before booking. Pets are welcome.

Popular amenities for waterfront rentals in Whitby

When is the best time to visit Whitby?

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Avg. price$83 SGD$87 SGD$94 SGD$83 SGD$79 SGD$89 SGD$93 SGD$102 SGD$92 SGD$83 SGD$83 SGD$88 SGD
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