Holiday rentals with a kayak in Greater Toronto and Hamilton Area

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Top-rated Accommodation with a Kayak in Greater Toronto and Hamilton Area

Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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Guest favourite

The exterior of the guest house features a wrap-around composite deck with glass railing, overlooking the direct waterfront views of Lake Ontario. The structure is surrounded by lush greenery and is complemented by large windows allowing natural light into the living space.

Guesthouse in Lincoln

4.96 out of 5 average rating, 324 reviews

Cottage On Lake Ontario Niagara

OPEN TIMESLOTS AUGUST 12-23 AUGUST 25-29 (4 nights/5 days) AUGUST 30-SEPTEMBER 3 (4 ni 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 orchards and the Lake.

LocationOutdoor spacesBackyard

Top Guest favourite

A wooden dock extends into a calm lake, reflecting fluffy white clouds and blue skies. Lush greenery is visible along the shoreline, creating a serene natural backdrop.

Cottage in Kawartha Lakes

4.93 out of 5 average rating, 197 reviews

Ke's Rustic Retreat in Kawartha Lakes

WELCOME TO KE’S PLACE! This ALL SEASONS rustic, private, 4 season, lakefront cottage on Pigeon Lake features 3 bedrooms, 3 full/double sized beds, large bright living room with sleeper sectional, newly renovated kitchen, two large decks, private dock, indoor fireplace, enclosed patio room, outdoor fire pit, and large yard for games and more. Located approximately 1.5 hours from Toronto, this cottage is the perfect place for families and friends to escape the hustle and bustle, relax and unwind.

Outdoor spacesValuePool

Top Guest favourite

An outdoor stone wall shower is positioned next to a wooden deck, leading to a private pond. The deck features a covered area with dining furniture. Lush greenery surrounds the space, and sunlight illuminates the scene under a clear blue sky.

Shipping container in Clarington

4.98 out of 5 average rating, 117 reviews

Rustic Ridge

Rustic Ridge Tiny Cabin - Cozy Escape on Private Pond **Cabin will have to be winterized when temperature drops meaning no running water and outdoor shower, jugs of water will be supplied to rinse after sauna, bottled water in dispenser also provided.*** Welcome to Rustic Ridge Tiny Cabin, a unique shipping container retreat on the back of our property. Nestled by a private pond with a fountain, this serene cabin is the perfect escape for nature lovers and those looking to unwind in comfort.

ValueLocationAmenities

Guest favourite

Cottage in Georgina

4.9 out of 5 average rating, 206 reviews

Waterfront Cottage-Sauna, Dock, 4-bed, 4 Parking

Bright and airy waterfront cottage in one of Lake Simcoe’s most desirable areas. The open-concept layout and unique lot design offer stunning lake views from almost every room. Enjoy custom furnishings, stylish decor, and a fully equipped kitchen—perfect for relaxing getaways or extended stays. Whether you're here for a peaceful retreat or lakeside fun, this cottage provides comfort, beauty, and convenience in a serene upscale setting. Ask us about fun activities that Lake Simcoe offers.

LocationOutdoor spacesParking

Top Guest favourite

Cottage in Innisfil

4.85 out of 5 average rating, 262 reviews

3BR on Lake Simcoe | Gorgeous Views 1hr From City

Escape the city and unwind at our peaceful three-bedroom lakefront cottage on Lake Simcoe, just one hour north of Toronto. With 129 feet of private waterfront, expansive lake views, and shallow swimmable shoreline, it’s the perfect year-round getaway for families, couples, or friends looking to relax and reconnect. 🌅 Stunning sunrise lake views 🏖️ 129 ft of private waterfront 🏊 Shallow, swimmable shoreline 🔥 Cozy all-season retreat 🌲 Quiet and peaceful setting 🚗 Just 1 hour from Toronto

ValueLocationComfort

Top Guest favourite

Cottage in Georgina

4.91 out of 5 average rating, 300 reviews

Lakefront | Hot Tub, Private Dock & Sandy Bottom

Luxury lakefront cottage on beautiful Lake Simcoe with a rare shallow sandy-bottom shoreline, private dock, and hot tub, perfect for swimming and family fun. Enjoy breathtaking sunsets, kayaking, paddleboarding, fishing, BBQ, and a fire pit. Ideal for family vacations and group getaways near Toronto, minutes from Hwy 404. Features 6 spacious bedrooms, 4 bathrooms, a fully equipped chef's kitchen, and a bright open-concept living area. Private, peaceful, and perfect for unforgettable memories.

LocationValueNearby

Guest favourite

Cottage in Georgina

4.96 out of 5 average rating, 134 reviews

Resort-Style Luxury Waterfront Cottage

Experience luxury at our 5-star, Superhost-rated waterfront cottage on Lake Simcoe, just 80 KM from Toronto! A guest favorite, it offers breathtaking sunsets and sunrises from the living room and loft. Relax on the sandy beach with waist-deep waters, and enjoy the patio, BBQ, bar, lounge, kayaking, and fishing. With a fully equipped kitchen, 3 bedrooms, and 2 bathrooms, it comfortably accommodates up to 8 guests. Book your dream getaway today for the perfect blend of relaxation and adventure!

Outdoor spacesLocationAccess

Superhost

An aerial view captures the waterfront trailer set against lush greenery, with a private deck featuring seating arrangements. Nearby, two kayaks await by the water, and a fire pit is surrounded by logs. The tranquil lake reflects the surrounding foliage.

Tiny home in Action

4.85 out of 5 average rating, 150 reviews

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.

LocationValueHeating

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, 211 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.

Outdoor spacesLocationBackyard

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, 196 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!

ValueOutdoor spacesTV

Top Guest favourite

Cottage in Cameron

4.93 out of 5 average rating, 106 reviews

Lakefront Cottage | 2 BR, Hot Tub, Fire Pit

Welcome to your private Kawartha Lakehouse retreat! This spacious home is the perfect luxury escape for couples, small families, or friends who want extra room to spread out and relax. Enjoy the comfort of a full-size lakehouse with only 2 bedrooms, giving you both privacy and space on the tranquil lakeside. Whether you’re planning a romantic getaway, a family trip with kids, or a work-from-the-lake escape, our home offers a cozy setup with the space and privacy of a full lakehouse.

Outdoor spacesLocationComfort

Top Guest favourite

Condo in Innisfil

4.97 out of 5 average rating, 176 reviews

Upscale Spa w/ Hot Tub-Private Sauna-Penthouse

Welcome to our most Dramatic & Romantic Penthouse Spa Getaway Suite! Reconnect with your loved one or celebrate that special milestone in our professionally designed to play with all your senses spa suite, this escape will leave you feeling refreshed and rejuvenated! Cozy up to any of 3 fire elements and then cleanse and detox in your own private in-suite Infrared Sauna! Cook up a gourmet meal in our fully equipped chef's dream kitchen and year round Weber BBQ for grilling!

LocationOutdoor spacesHot tub